Professional Documents
Culture Documents
(Advances in Ccarbohydrate Chemistry and Biochemistry Volume 54) Derek Horton-Cumulative Subject and Author Indexes, and Tables of Contents For Volumes 1-53-Academic Press (1999)
(Advances in Ccarbohydrate Chemistry and Biochemistry Volume 54) Derek Horton-Cumulative Subject and Author Indexes, and Tables of Contents For Volumes 1-53-Academic Press (1999)
Board of Advisors
LAURENS ANDERSON DAVtD R. BUNDLE
STEPHENJ. ANGYAL STEPHEN HANESSIAN
HANSH. BAER BENGTLINDBERG
CLINTON E. BALLOU HANSPAULSEN
JOHNS. BRIMACOMBE NATHAN SHARON
J. GRANTBUCHANAN J. F. G. VLIEGENTHART
ROYL. WHISTLER
Volume 54
Cumulative Subject and Contributor Indexes
and Tables of Contents
Volumes 1-53
ACADEMIC PRESS
San Diego London Boston New York
Sydney Tokyo Toronto
This book is printed on acid-free paper. @
The appearance of the code at the bottom of the first page of a chapter in this book
indicates the Publishers consent that copies of the chapter may be made for
personal or internal use of specific clients. This consent is given on the condition,
however, that the copier pay the stated per copy fee through the Copyright Clearance
Center, Inc. (222 Rosewood Drive, Danvers, Massachusetts 01923), for copying
beyond that permitted by Sections 107 or 108 of the U.S. Copyright Law. This consent
does not extend to other kinds of copying, such as copying for general distribution, for
advertising or promotional purposes, for creating new collective works, or for resale.
Copy fees for pre-2000 chapters are as shown on the title pages. If no fee code
appears on the title page, the copy fee is the same as for current chapters.
0065-23 18/00 $30.00
Academic Press
A Harcourt Science and Technology Company
525 B Street, Suite 1900, San Diego, California 92101-4495, USA
http://www.apnet.com
Academic Press
24-28 Oval Road, London NWl 7DX, UK
http:l/www.hbuk.co.uk/ap/
V
This Page Intentionally Left Blank
PREFACE
such an index for volumes 1-29, while those appearing in volumes 35, 40, 45,
and 50 refer in each case to the preceding five volumes.
The present index volume largely follows the model used successfully for the
Methods in Enzymology series published by Academic Press, and the cumulative
subject index has been compiled directly from subject indexes in the individual
volumes. It is recognized that a lack of total uniformity is inevitable as a conse-
quence of unevenness in some of the indexes, and most importantly, from the
progress that has been made toward uniformity in carbohydrate nomenclature.
Current nomenclature recommendations are recorded in the 1996 document
Nomenclature of Carbohydrates, issued by the International Union of Pure and
Applied Chemistry and the International Union of Biochemistry and Molecular
Biology, which has been published in Volume 52 of Advances in Carbohydrate
Chemistry and Biochemistry.
This index volume is complemented by a cumulative contributor index, and it
is hoped that the volume will facilitate the retrieval of information and signifi-
cantly enhance the utility of the entire series.
Washington, DC DEREKHORTON
June 1999
CONTENTS OF VOLUMES 1-53
VOLUME 1
CarbohydrateOrthoesters ..................................................... 77
EUGENEPACSU
VOLUME 2
ix
X CONTENTS OF VOLUMES 1-53
Synthesis of Hexitols and Pentitols from Unsaturated Polyhydric Alcohols ............. 107
R. LESPLEAU
VOLUME 3
Historical Aspects of Emil Fischers Fundamental Conventions for
Writing Stereo-Formulas in a Plane ............................................. 1
C. S. HUDSON
TritylEthersofCarbobydrates ................................................. 79
BURCKHARDT HELFERICH
Glutose and the Unfermentable Reducing Substances in Cane Molasses ............... 113
LOUISSATTLER
VOLUME 4
The Acylated Nitriles of Aldonic Acids and Their Degradation .. . . .. . .. . . . .. .. .. . . ... 119
VENANCIO DEULOFEU
VOLUME 5
.
Action of Certain Alpha Amylases . . .. .. . . . . . .. . . .. .. . . . .... .. .. .. .. .. .... .. .. . . 229
MARYL. CALDWELL AND MILDRED ADAMS
VOLUME 6
The Methyl Ethers of he galactose .. . . .. .... . ... .. . . . .. ... .. .... . . .. .. .. .... . . ... 11
D. J. BELL
VOLUME 7
Acetals and Ketals of the Tetritols, Pentitols, and Hexitols . . . . . . . . .. . . . ... . . . . .. . . . . . 137
S. A. BARKER AND E. J. BOURNE
VOLUME 8
VOLUME 9
Carboxymethylcellulose . . .. . . . . . . . . . . .. . .. .. . . . . . .. . . . . . . . . .. . . . . . .. . . . . .. . . .. 28.5
A N D MARJORIE
J. V. KARABINOS Hmmu
VOLUME 10
.
Glycosylamines . . . .. . . . . . .. .
. . . .. . . . . . . ... .. . .. . . . . . . . .. . . . .. .. . ... . .. .. . . . . . 95
G. P. ELLISAND JOHN HONEYMAN
The Methyl Ethers of the Aldopentoses and of Rhamnose and Fucose . . . . . .. . . . .. . . .. . 257
GEORGE G. MAHER
VOLUME 11
TheOsones . ..
..... ... ...... .. . . .. . .. .. .. . ..... . .... .. ... ............ .. . .. ... 43
S. BAYNE
AND J. A. FEWSTER
VOLUME 12
InfraredSpectraofCarbohydrates .............................................. 13
W. BROCKNEELY
The Saccharinic Acids .... .. .. .. . . ... .. .... . ... .. .. .. .... . ... .... . .. .. .. . . .. . . . 35
JOHNC. SOWDEN
VOLUME 13
.
The Nonulosaminic Acids . . . .. . . . . . .. . . . .. .. . . ... .. .. .. . .... . . . . . . . . . . . .. . . . .. 237
F. ZILLIKEN
AND M. W. WHITEHOUSE
VOLUME 14
VOLUME 15
VOLUME 16
VOLUME 17
VOLUME 18
Photochemistry of Carbohydrates . . . .. . . . .. . .. . . . .. . . . .. . . . .. . . . . . . . . . . I 9
GLYN0. PHILLIPS
xx CONTENTS OF VOLUMES 1-53
Chemistry of the Amino Sugars Derived from Antibiotic Substances .................. 259
JAMESD. DUTCHER
VOLUME 19
NuclearMagneticResouance ................................................... 51
L. D. HALL
The Action of Hydrogen Peroxide on Carbohydrates and Related Compounds .......... 149
G. J. MOODY
3-Deoxyglycosuloses(3-Deoxyglycosones)and
the Degradation ofcarbohydrates ............................................... 181
E. F. L. J. ANET
VOLUME 20
.
Wood Hemicelluloses: Part I1 . . . . . . . .. . . . . . .. . .. .. . . . .. . . . . .. . .. . . . . . . .. .. .. .. . 410
T. E. TIMELL
VOLUME 21
KARLFREUDENBERG
Mass Spectrometry of Carbohydrate Derivatives .. . .. .. .. . .. . . ... .. .. .. . . . . . . . .. .. 39
N. K. KOCHETKOVAND 0. S. CHIZIIOV
TheGlycofuranosides ......................................................... 95
JOHNW. GREEN 95
xxii CONTENTS OF VOLUMES 1-53
Complexes of Alkali Metals and Alkaline-Earth Metals with Carbohydrates . .... . ... .. 209
J. A. RENDLEMAN,JR.
The Effects of Plant-Growth Substances on Carbohydrate Systems ... .. .... ... . . .... , 377
H. W. HILTON
VOLUME 22
Acetolysis ................................................................... 11
R. D. GUTHRIE
AND J. F. MCCARTHY
VOLUME 23
VOLUME 24
RichardKuhn(1900-1967) ..................................................... 1
HANSH. BAER
TheNitroSugars ............................................................. 67
HANSH. BAER
Glycosphingolipids
(Sugar-Sphingosine Conjugates) ................................................ 381
J. KISS
VOLUME 25
VOLUME 26
Tables of the Properties of Deoxy Sugars and Their Simple Derivatives ................ 279
ROGERF. BUTTERWORTH AND STEPHEN HANESSIAN
Morphology and Biogenesis of Cellulose and Plant Cell Walls ........................ 297
AND G. D. MCGINNIS
F. SHAFIZADEH
VOLUME 27
VOLUME 28
VOLUME 29
BernardRandallBaker(1915-1971) ............................................. 1
LEONGOODMAN
VOLUME 30
DavidJamesBell(1905-1972) .................................................. 1
JOHNS. D. BACONAND DAVIDJ. MANNERS
VOLUME 31
VOLUME 32
VOLUME 33
VOLUME 34
EdwardJohnBourne(1922-1974) ............................................... 1
HELMUTWEIGEL
VOLUME 35
.
Edmund Langley Hirst (1898-1975) . . . . . . . . . . . . . . . .... . . . .. . .. . . . . ... .. .. .. . .. . 1
MAURICESTACEY AND DAVID J. MANNERS
CarbohydrateBoronates ....................................................... 31
ROBERTJ. FERRIER
VOLUME 36
JohnArcherMills(1919-1977) .................................................. 1
STEPHEN
J. ~ G Y A L
Bibliography of Crystal Structures of Polysaccharides, 1976 . . ... ... . ..... .. ..... . ... 315
PUDUPADl R. SUNDARARAJAN AND ROBERT H. MARCHESSALTLT
VOLUME 37
VOLUME 38
EmilHardegger(1913-1978) ................................................... 1
HASSANS. EL KHADEM
VOLUME 39
KarlPaulGerhardtLink(1901-1978) ............................................ 1
CLINTONE. BALLOU
xxxii CONTENTS OF VOLUMES 1-53
VOLUME 40
VOLUME 41
VOLUME 42
DexterFrench(1918-1981) ..................................................... 1
JOHNH. PAZUR
Sugar Analogs Having Phosphorus in the Hemiacetal Ring .. .. ... . . . . . . .. . . . . ... .. .. 135
HlROSHl YAMAMOTO AND SABURO INOKAWA
Carbon-13 Nuclear Magnetic Resonance Data for Oligosaccharides . . . .. .. .. .. ... ..... 193
K L A U S BOCK,CHRISTIAN PEDERSEN, A N D HENRIK
PEDERSEN
VOLUME 43
VOLUME 44
FredShafuadeb,1924-1983 ....................................................
GARYD. MCGINNIS
VibrationalSpectraofCarbohydrates ............................................
MOHAMED MATHLOUTHI AND JACKL. KOENIG
VOLUME 45
The Chemistry and Biochemistry of the Sweetness of Sugars . ... .. .. .. . .. . . . ... .. .. . . 199
CHEANG-KUAN LEE
VOLUME 46
KonoshinOnodera,1910-1983 .................................................. 1
TOIiRU KOMANO
AND NAOKIG S H I M U R A
VenancioDeulofeu,1902-1984 .................................................. 11
ROSAM. DE LEDERKREMER AND EDUARDOG. GROS
VOLUME 47
VOLUME 48
HamaoUmezawa,1914-1986 ................................................... 1
TSUTOMU
TSUCHIYA,KENJIMAEDA,AND DEREKHORTON
VOLUME 49
1,4:3,6-Dianhydrohexitols ...................................................... 93
PETERSTOSSAND REINHARD
HEMMER
VOLUME 50
VOLUME 51
HoraceS.Isbell,1898-1992 ..................................................... 1
HASSANS. EL KHADEM
VOLUME 52
VOLUME 53
HarrietL.Frush,1903-1996 ......................................... 13
HASSANS. EL KHADEM
I
2 SUBJECT INDEX
mineral and Lewis acids, 32:60 70 w-deoxy sugars by catalytic reduction of,
spectroscopic properties of, 32:8X 98 21:176
ofsugars, 32:IS-123 Acetamide
sulfonic esters, fonnation and reaciions N-[5-( I ,2-dihydroxyethyl)-3-furyl]-.
of, 3248-52 formation of, 28:202
in synthesis, 32: 16 ~~,O-bis(trimethylsilyl)-. trimethylsilylation
tritylation of, 32:46 with, 28:26
of 2-amino-2-deoxyaldoses, deamination trifluoro-N-methyl-N-(trimethylsily1)-.
of, 25: 192 trimethylsilylation with, 28:28
gas-liquid chromatography of, 30:33 trifluoro-N.0-bis(triniethylsily1)-, as
glycoside synthesis by alcoholysis of trimethylsilylating agent, 28:27, 80
acyclic sugar. 34:244 Acetamidodeoxyhexosidase, in Tay-Sachs
mass spectra of sugar, 29:7 1-73 discasc, 31:6
photolysis. 38: 150-1 53 Acetamido group
selective esterification of carbohydrate, effect on acyloxoniurn rearrangements.
33:4041 26:161
selective methylation of carbohydraic. oligosaccharides containing, ' T - N M R data
33:65-66 for, 42:209-2 I0
sugar, 26: I3 participation i n sugar reactions, 22: 127
in 1-thioglycosiduronic acid prcparation, Acetanilide, metabolism, 36:9 1
36: 10&102 2-Acetate. trorworiented. nucleophilic attack
exchange of, 34: 186-1 88, 192 on carbonyl group, 51:7. 10
gas-liquid chromatographic detemii nation Acetates
of, 30:35 circular dichroism. 45: 120- 122
of hexitols, pentitols, and tetritols, gas-liquid chromatography of
7: 137-207 alditol, 30:30 -32
hydrolysis mass spectrometry of, 30:40
(acid-catalyzed) of, 22:30, 59, I 13 of methylated alditols, 30:89-98
selective, 39: 14-24 of niethylated aldononitriles, 30: I00
isomerization, 39:26-28 of niethylated methyl glycosides. 30:26,
isopropylidene. in gas-liquid 82
chromatography, 28:37 of methylated sugars, 30:29. 86
mercaptalation of, 32:28
of monosaccharides, mass spcctra of, mass spectrometry of, aldononitrile.
21:74 methylated. 30:43
nomenclature, 52: 123-1 24 Acetic acid
cyclic, 52:121-122 (2,3-0-isopropylidene-P-r~-ribofuranosyl)-,
of polyhydric alcohols, mass spectra of. ethyl ester, preparation of, 33:157
21:79 bromo-. cellulose ester, preparation of,
of polysaccharides, preparation of: 29:339 29:337
preparation bromo (2,3,4,6-tetra-O-acety 1-P-o-
from dithioacetals, 32:65 glucopyranosy1)-, methyl ester,
from en01 ethers, 34: 1 88 preparation of, 33:146-147
propane- I ,3-diyl dithio-, preparation of, as catalyst in osazone formation, 22:264
3239 chloro-
protection as, 46: 182-1 X9 as catalyst for polymerization of 1.6-
rearrangements of, 26:220 anhydro sugars, 2 1 :486
synthesis of, 34: 182-1 92 as solvent for sucrose, 27: 104
trimethylene dithio-, preparation of, (4-chloro-2-methy1phenoxy)-
32: 37-38 effect on sugarcane. 21 :427
4 SUBJECT INDEX
5-deoxy-5-phosphino-and-5-phosphinyl-, 4ldoses
ORTEP representation, 42: 163 2-amino-2-deoxy-, deamination and micro
structural analysis of, 42:161-176 determination or detection of, 31:71
2,6-diamino-2,3,4,6-tetradeoxy-, synthesis, 4-acetamido-4-deoxy-, 23: 178
40:4748 acylated, thioglycosides preparation, 52: 18 1
orientation, 47:48, 5 1 acyl esters, ammonolysis of, 31539
sweetness, and structure, 45:239-248 acyloxonium derivatives, preparation and
I-thio-, conformation of, 26:87 rearrangement of, 26: 146
5-thio-, mutarotation of, 24:49 aldehydo-
5-thio-, oxidation of sulfur in, 23:2 12 acetates, preparation of, 32:62
Aldopyranosides reaction with diazomethane, 32:64
acidic degradation of, 28: 180 2-5-anhydridq mutarotation of, 25:2 I3
alkyl2,3-anhydro-4-deoxy- conformation of peracetates of o-ribo. D-
configuration, 40:44 arabino-, o-xylo, o-lyxo-, and L-
ring opening reactions, 40:4447 galacto-, 26:72
aIkyl3,4-anhydro-o~- aldonolactone reduction to, 50: 157- I61
oxirane-ring opening, 40:57-59 and aldosides, cyclic acetals of, 20:2 19-
synthesis, 40:56 302
p-, 48~327 5-(alkylamino)-5-deoxy-,23: 139
hydrolysis by alkali, 21:137 amino-, deamination of, 25: 183- 194,
hydrolysis of, rate constants for, 22:42 33:114116
methyl 2-amino-2-deoxy-
cuprammonia complexes in deamination of, 33: 114-1 16
conformational analysis, 26:64 dithioacetals, deamination of, 25: 192
infrared spectroscopy and conformational synthesis of, 24:9, 1 12, 265
analysis of, 26:54 4-amino-4-deoxy-, 23: 147
methyl 2,3- and 3,4-anhydro-, conformations 6-amino-6-deoxy-, 23: I55
of, 26: 124 anhydrides of, formation in aqueous solution,
methyl D- 42:35
conformation in solution, 26:84 2,5-anhydro-, 25:182, 185
optical rotation and conformation of, color reaction for, 25:216
26:61 dimethyl acetals, synthesis of, 33: I26
methyl 3,4-dideoxy-3-(dimethylamino)-r)~-, preparation by deamination, 33: I 14
N-oxide, Cope degradation, 40:5 1 preparation from glycosyl cyanides,
valence geometry parameters, 47:72 33:131-142
Aldopyranosuloses, unsaturated, synthesis, synthetic routes to, 33: 1 15
40:6412 hemiacetals, 25212
Aldopyranosyl fluorides, polyglycoses from, reactivity of, 25:210
21:460 2-6-anhydro-, 24:211
Aldopyranosyl halides, conformations of, effect 3,6-anhydro-, by alkaline degradation,
of halogen on, 26:87 28:202
Aldose anhydro-C-(p-methoxyphenyl), synthesis
amides, preparation of, 31:82, 84, 89 and properties of, 27:28&292
isomerization of, to ketose, with hydride anomeric, equilibrium proportions of, 23:3 1
shift, 46:287 in aqueous solution, 49:25-26
liquid chromatography methods for analysis composition, 42:21,3437
of, 46:33 liquid chromatography, 42:23-24
transformations, basic conditions, 46:28 I branched-and straight-chain, in formose,
Aldoseptanosides, hydrolysis of, rate constants 29:2 13-2 15
for, 22:42 branched-chain sugars, 48:287-288
22 SUBJECT INDEX
D- 3-amino-2.3,6-trideoxy-2-fluoro-6-
complexes, 34:54 halogeno-a-. derivatives
formation of, 34:47 IH- and I9F-NMR data for, 46: 123
3-deoxy-3-fluoro-P-o-, preparation of, N-containing synthetic precursors, 'H-
34:133 and "F-NMR data for, 46: 123
3-deoxy-3-iodo-2-0- 3-benzamido-4-O-ben~oyl-6-bromo-, "C-
(methylthio)carbonyl-P-D-, crystal NMR data for, 46: 170
structure, 43:220-22 1 benzyl3-benzamido-2,3,6-tndeoxy-2-
3-deoxy-3-nitro-P-~-,preparation of. fluoro-a-, 'H-and "F-NMR data for,
34:105, 126 46: 123
3,4-dideoxy-3,4-epimino-P-~-, preparation benzyl2,3-dideoxy-2-tluoro-a-
and properties of, 34: 124- 125, 3-azido-6-O-(methylsu1fonyl)-. 'H- and
130-131 I9F-NMR data for. 46: 1 18
2-0-benzoyl-3-0-p-tolylsulfonyl-~-~-, 3-benzamido-, 'H- and I9F-NMR data
preparation of, 34231 for, 46: 1 18
3,4-0-isopropylidene-P-~-, as synthetic 3-benzamido-6-0-mesyl-, 'H- and "F-
intermediate, 34:90 NMR data for, 46: 1 I8
2-O-(methyhlfonyl)-P-~-,reaction with 3-benzamido-6-O-tosyl-, IH- and IYF-
potassium fluoride, 38:220-22 1 NMR data for, 46: 1 I8
3-S-benzy1-3-thio-o-, preparation of, benzyl2-fluoro-a-, 3-benzamido-2,3,6-
34: I36 tr~deoxy-,~~C-NMR data for. 46: 170
2,3,4-tri-0-benZyl-P-D-, polymerization, benzyl 2-fluoro-2,3,6-tndeoxy-6-1odo-a-
39:182, 187 3-azido-, 'H- and "F-NMR data for,
anhydro-4-~-benzyl-3-deoxy-3-fluoro-~-~-, 46: 123
2-0-acetyl-1,6-, 'H- and 19F-NMRdata 3-benzdmido-, 'H- and '"F-NMR data
for, 46: 1 14 for, 46: I23
D- methyl 3-benzamido-2,3-dideoxy-2-
orientation of hydroxyl groups for, in fluoro-a-
4 C , ( ~conformation,
) 45:75 4,6-di-O-benzoyl-, 'H- and "F-NMR
pentaacetate, conformation of, 26: I02 data for, 46: 1 I8
1,6:3,4-dianhydro-P-~-,25:113.48: 163- 4,6-0-acetyl-, 'H-and "F-NMR data
164 for, 46: I 18
preparation of, 34: 108, 1 13 4,6-0-benzyhdene-, 'H- and "F-NMR
1,2:3,4-di-O-isopropylidene-P-~-, hydrolysis data for, 46: 1 18
of, 34:204 methyl 4-O-benzoyl-6-bromo-2.3,6-
penta-0-acetyl-a-o-, crystal structure trideoxy-2-fluoro-a-
bibliography, 34:360 3-benzamido-, 'H- and I9F-NMR data
tri-0-acetyl- 1,6-anhydro-P-o-, reaction with for, 46: I23
trifluoromethanesulfonic acid. 34:87 3-(trifluoroacetamido)-, IH- and "F-
Altropyranose pentaacetate. carba- NMR data for, 46: 123
a-DL-, synthesis, 48:28-29 methyl 4,6-0-benzyliden-2,3-di-deoxy-2-
u-D-,synthesis, 48:44 fluoro-cx-
a-L-, synthesis, 48:46 3-(diallylamino)-, 'H- and "F-NMR
Altropyranoside data for, 46: 1 18
D- 3-(trifluoroacetamido)-, 'H- and I9F-
3-amino-2,3-dideoxy-2-fluoro-a-, NMRdata for, 46: 1 18
derivatives methyl 2.3.6-trideoxy-2-fluoro-a-
'H- and I9F-NMRdata for, 46: I 17- I I8 3-amlno-
N-containing, synthetic precursors, ' H- "C-NMR data for, 46: 170
and "F-NMR data for, 46: I I 7- I I8 'H- and "F-NMR data for, 46:123
32 SUBJECT INDEX
Arabinopyranoside (continued) D-
methyl 3.4-O-endo-ethylidene-fb~- 2-deoxy-
irradiation, 39:93 2-bromo-P-, 'H- and I9F-NMR data for,
synthesis, 39:79 46:135
methyl 3,4-0-ethylidene-P-~-. 3,4-di-O-acetyl-2-bromo-u-, 'H- and
photochemical reaction mechanism with "F-NMR data for, 46:135
excited acetone, 38: 143 3,4-di-O-acety1-2-iodo-a-, IH- and I9F-
preparation of, 34: 190 NMR data for, 46:135
methyl 3,5-U-(ethyl orthoacetyl)-P-L-, 3,4-di-O-acetyl-2-deoxy-2-fluoro-P-, 'H-
acetoxonium fluoroborate, 26: 168 and "F-NMR data for, 46: 155
methyl 3,4-O-isopropylidene- 3,4-di-0-acetyl-2-O-methyl-p-, 'H- and
p-L-,23~276 I9F-NMR data for, 46: 101
reaction with N-(2-chloro-l, 1.2- 3,4-di-0-benzoyl-2-0-methyl-, 'H- and
trifluoroethyl)diethylamine,28:258 "F-NMR data for, 46:lOI-102
2-0-methyl p-D-, reaction with 3,4-0-acetoxonium-2-0-methyl-, 'H- and
butyllithium, 39: 142 "F-NMR data for, 46:lOl
2-0-methyl-P-~-,sulfonylation of, 3.4-0-benzoxonium-2-0-methyl-, 'H- and
23:238 I9F-NMR data for, 46:lOl
2-O-p-tolysulfonyl-P-o-, displacement 3(or 4)-0-benzoyl-2-O-methyl-~-,'H- and
reactions of, 24:152 '"F-NMR data for, 46:102
methyl 4-O-methyl-u-~~-, preparation of, 2,3,4-tri-O-acetyl-,'H- and 19F-NMR data
28:296 for, 46: 101
methyl 2-0-methyl-p-~-,benzoylation of, 2,3,4-tri-O-acetyl-P-, I3C-NMR data for,
33:25 46: I67
methyl 2-U-(methylsulfonyl)- p-D-, 23:260 2,3,4-tri-0-benzoyl-~-, 'H- and "F-NMR
methyl 2-0-p-tolylsulfonyl-~-~-, 23:260 data for, 46: 101
methyl tri-0-methyl-P-D-, mass spectrum of, 3-deoxy-3-fluoro-
21:60 p-D-,preparation, 38:213
methyl 2,3,4-tri-O-methyl- D-, preparation, 38:213
p-L-,mass spectrum of, 21:48 2-deoxy-2-fluoro-o-, preparation, 38:2 14,
D-, mass spectrum of, 23:202 245
methyl tri-0-(methylsulfony1)-a+(and p- di-O-acetyl-2-bromo-2-deoxy-p-~-,
L)-, displacement reactions of, 24: 161 preparation, 38:235
2-O-methyl-o-, from 3-0-methyl-D-glucose 3,4-di-0-acetyl-2-deoxy-2-fluoro-p-~-,
by oxidation, 33:98 preparation, 38:233
p-nitrophenyl a-L-,as U-L- 3,4-di-0-benzoyl-2-0-methyl-o-, anomers,
arabinohranosidase substrate, 42:390 synthesis, 38:201
trifluoromethyl 3,4-di-O-acetyl-2-deoxy-2- tri-O-acetyl-p-~-,proton magnetic resonance
fluoro-p-D-, preparation, 38:233 spectroscopy of, 27:82
Arabinopyranosylamine, N-acetyl-u-L-, tri-0-benzoyl-
configuration of, 31:104 U-D-, 26: 177
Arabinopyranosyl azide, tn-0-acetyl-u-o-, p-D-.26: 179
crystal structure bibliography, 32363 Arabinopyranosyl isothiocyanate, 2,3,4-tri-0-
Arabinopyranosyl chloride, 4-chloro-4-deoxy- acetyl-a-o-, 44:141
~-,2,3,-di(chlorosulfate), preparation of, I3C NMR, 44:141
28:235 formation of amino acid diastereoisomers
Arabinopyranosyl fluoride using, 44: 1 17
2-bromo-2-deoxy- infrared spectrum, 44: 141
a-D-,crystal structure of, 25:74 Arabinopyranosylmethane,bis(ethylsulfony1)-
P-D-, 24:204 U-D-, triacetate, nuclear magnetic
SUBJECT INDEX 53
6-Azauridine B
crystal structure bibliography, 31:355
5-niethy1, 5-phosphate, 22:373 Bacillosamine, 23: 155
5-phosphate, 22373 Bacillus circuluns, trehalase from, 30:25 1
monohydrate, crystal structure Bacillus licheniformis peptidoglycan, crystal
bibliography, 31:359 structure bibliography, 40:399
trihydrate, crystal structure, 43:273-274 Bacillus maceruns, 46:212, 2 15-217
selective tritylation of, 33:5 1 cyclodextrin transglycosylase, 46:207
2,3,5-tri-O-formyl-,methanolysis, Bacillus potvniyxa, polysaccharide, 36:300
selective, 39:37 Bacillus .subtitis
Azepine, sugar derivatives, 25:404 a-1.-arabinofuranosidase from, 42387-388
Azides endo-L-arabinanase in, 42392-393
anomeric as precursors, 50:278-280 L-arabinanases from, 42:384, 391
I ,4:3,6-dianhydrohexitols,49: 154 teichoic acid from, 21:350, 354
irradiation of carbohydrate, 38: 176-178, Bucillus thrtringiensis, exotoxin from,
180-1 84 preparation of, 34: 170
sugar, aziridine sugars from, 25:354 Bacitracin
Azido ketonucleosides, synthesis of, 42:257 effect on peptidoglycan biosynthesis,
2-(2-Azidophenyl)ethyl 26:43 1
alcohol, 46:200 inhibition of protein glycosylation,
photocyclization of, 46:201 40:325-326
Azido-pheylselenylation, 53: 16 1-1 67 Bacteria, see also specific species
Azidosphingosine, derivatives, glycosylation a+-trehalose in, 30:230,234
with trichloroacetimidates, 50:41, amphiphiles, 44:277
45-48 cell-walls
Azines extension in, 42:51
of o-fructose, 22:280, 303 lipopolysaccharides of gram-negative,
irradiation of carbohydrate, 38: I86 26:409424
Aziridirie ring peptidoglycan in, 26:424432
fonnation in sugar reactions, 22: 143, 146, synthesis. 44:342
151 dextran-synthesizing, 30:373
saccharides containing, 25:352-356 gas-liquid chromatograpliic analysis for,
stability of, 34: 13I 28:XI
Aziridines glucansucrases, 51: 138-139
glucosidase inhibition, 48:37 1-373 glycolipides of acid-fast, 16:207-238
preparation of, 27:257,264 gram-negative
reaction with nitrous acid, 31:66 extracts, gas-liquid chromatography of,
Aziridinium chloride, N,N-diethyl-, and 28:59
reactivities of hydroxyl groups toward, lacking lipopolysaccharides, 50:262-263
33:57 infection, immune response of capsular
Aziridino ketonucleosides, synthesis of, 42: polysaccharides, 41: 186-191
257 lipopolysaccharides, 44:277
Aziridinyl groups, anomeric effects, solvent 0-specific chains, biosynthesis,
effects, 47:68-69 44:3 12-3 I9
Azoospermia, o-fructose level in, 34:304 block mechanism, 44:3 12-3 18
Azo-proteins, preparation and properties, monomeric mechanism, 44:3 18-3 19
37:230 structure, enzymic analysis, 44:230-23 1
Azotohacter indicum, see Belierinckia indicu mass spectrometry of polysaccharides from,
Azulenes, C-glycosylation in preparation of, 29:66
33: 159 nucleosides and nucleotides of, 15:201-234
SUBJECT INDEX 61
Carbohydrases, endo and exo actions of, action of hydrogen peroxide on, 19:149-
29:340 179
Carbohydrate. chains acyclic, selective esterification of
proton nuclear magnetic resonance dithioacetals of. 33:4041
spectroscopy of glycoprotein-related, selective methylation of, 33:65-66
4 1:2 10-3 74 acyl esters, reaction with ammonia,
structural reporter groups, 41:212 31:81-134
Carbohydrate-alkali metal alcoholate affinity chromatography adsorbents for
complexes, 21:260 macromolecular substances,
Carbohydrate amines, deamination of, and 39:405-447
related compounds, 31:9-79 anomeric carbon atom, 47: 102
Carbohydrate-amino acid linkages, see ~ S < J anomeric region, 44: I I , I9
Glycosyl linkage anti. see Anti-carbohydrate antibodies
structures, 43:4-6 application of trifluoroacetic anhydride in
types, 43:4-6 chemistry of, 16:59-84
Carbohydrate anomers, separation of, 46: applications of reductive desulfurization by
70-7 1 Raney nickel, in the field of, 5: 1-28
Carbohydrate-binding specificity, of lectins, asymmetric carbon atom source, 27:205
35:139-145,331-333 benzyl ethers in synthesis of, 31:4
Carbohydrate chemistry, Wittig reaction in, boronates, see Boronates
27:227-299 branched-chain. by fomiose reaction,
Carbohydrate esters, photochemical reactions, 29:209-2 16
38: 136-142 butaneboronates, in gas-liquid
Carbohydrate-metal base complexes, 2 1 :237 chromatography. 28: 3 8
Carbohydrate-metal salt complexes carbonates of. 15:91-158
electrophoresis, 21:23 1 catabolism in yeasts, central pathways of,
optical rotations of, 21:228 32: 160-1 6 I
preparation of, 21:2 16-220 charge requirements, 47: 128
proof of existence of, 21 :2 1 1 CH,OH group. determination of rotational
solvation of, 21:226 isomerism, 44:53
stability of. 21:227 'T-labelled, preparation of, 32:8
stoichiometry of, 21:222 complex carbohydrates
structure of, 21:236 biosynthesis, in plants, 44:358-377
Carbohydrate-peptide linkage, of regulation mechanisms, 44:376-378
glycoproteins, 2 5 4 6 7 4 7 2 f.a.b.-mass spectrometry, 4559-62
Carbohydrate polymers, compositional analysis complexes with alkali metals and alkaline-
of, 46:5457 earth metals, 21:209-271
Carbohydrate-protein compounds, in urine as components of cardiac glycosides.
(human), 24:435452 1:147-173
Carbohydrate-protein linkages, 2 9 4 17-43') conformation
amino acid and carbohydrate residues, and interactions of, vibrational
50~277-278 spectroscopic study, 44:87-88
proteoglycans, 49:242-243 vibrational spectra used to analyzc.
structural analysis, 43:6 44:25-26
type, distinguished by I3C-NMR constitution of, 15: 11-51
spectroscopy, 43: 10 in con) syrup. 36:29
unusual, 43:4449 crystalline, radiation-induced, free-radical
model compounds, 43:4547 reactions, 37:67-74
Carbohydrates, see also Food, carbohydrates crystal structure
acetals. photochemistry, 38: 142-147 analysis of, 19:7-22
76 SUBJECT INDEX
cycloaddition, furan and acrylic acid, Difluorinated hex-5-enofuranoses, 'H and I9F-
racemic carba-sugars, synthesis, NMR data for, 46: IS4
48:29-36 2P.6P-Difluoroandrost-4-ene-3,I 7-dione.
product, 24: 129 48: 165
L- I ,6-Diepicastanospetmine, SO: 198- I99 3,3-Difluoro-3-de( methoxy)sporaricin A,
Dietetic foods, hexitols in, gas-liquid 48:223
chromatographic estimation of, 28:58 Difluorofuranoses, 3,6-anhydro-6,6-, 48: 153
Diethanolamine, see also 2,2'-Iminodiethanol Difluorogalactopyranose, 6-deoxy-6,6-
from aminolysis of sucrose, 27:99 I ,2:3,4-di-O-isopropylidene-a-~-, IH-and
Diethidium 5-iodocytidylyl-(3',5')-guanosine, I9F-NMR data for, 46: I5 1
27 hydrate, crystal structure bibliography, 1,2,3,4-tetra-O-acetyI-i,-,'H-and "F-NMR
38:502-503 data for. 46:150-151
Diethidium 5-iodouridylyl-(3 '+5 ')-adenosine, Difluorokanamycin A
27 hydrate, crystal structure bibliography, 4,6-dideoxy-4-epi-4,6-. 48:226
38:501-502 5,6-dideoxy-S-epi-5,6-, 48:225
Diethylamine Difluoromethylenation, aldonolactones.
(2-chloro-I , 1,2-trifluoroethyI), fluorinating 50: 145- 146
agent, 38:227-229 Difluorosucrose. 6,6'-dideoxy-6,6'-. 48:2 16
N-(2-chloro-l, 1,2-trifluoroethyl)- Difluoro sugars, 2-deoxy-2,2-, synthesis,
fluorinating agent, 38:227-229 48:181 182
reactions with alcohols and carbohydrates, Difluorouridiiie, 2',3'-dideoxy-3.'5'-, synthesis
28:257 and biological activity, 48:256
Diethy lamine, reducing sugar behavior in. Di-P-o-fiuctopyranose 1,2':1 '2-dianhydride,
42:34 47: 17,26
Diethylaminosulfur trifluoride, fluorinating Difructose anhydrides, 2:253-277,
agent, 38:225 52:211-212,240
Diethyl dithioacetals, circular dichroism. formation, S2:2 19
45: I23 Digalactosylceramide, biosynthesis, 40:248
Diethylenetriamine-guanosine-palladium(I1) Digalacturonopolygalacturonase,nomenclature,
bisperchlorate, crystal structure, 33:327
43 ~328-329 m-Digallic acid, 21:25
Diethyl ether, as solvent for sucrose, 27:87 Digestibility, 53:399400
Diethyl-hi-(trimethyIsilyl)amine, Digipronin, 39:302
trimethylsilylation with, 28:28 Digitalis pttrpitrra
Diferulic acid, esters, in ryegrass cell-walls, flavonoid from, 31:145
36:260 glucoapiosylapigenin from. 31: 175
in xylans, 36:242 Digitalose
Differential scanning calorimetry, I ,4:3,6- occurrence, 39:28 I
dianhydrohexitols, 49: 119 steroid glycosides, 39:302
Differential thermal analysis, starch, synthesis of. 32:65
47:299-300 Digitoxal, 3,4-di-O-nitrobenzoyI-, 2 1:299
Diffusion, agar, 53:205-206 Digitoxigenin, 21:273
Diffusion coefficients a-and P-o-rhamnosides, synthesis of, 27:4
of a-amylases, 23:309 a-r-rhamnopyranoside, preparation of, 27:4
of P-amylases, 23:333 3-U-(or-r-rhamnopyranosy)-, 21279
of phosphorylases, 23:348 8,14-anhydro-. structure of, 2 5 5 5
Diffusion-in-a-cone model, 51: 119-120. 126 anhydro-, 21:279
Diffusion measurement, enzyme molecular- 3-O-(~-u-glucopyranosyl)-, 21:282,3 12
weight determination by, 23:287 3-(2-deoxy-a-i) arubino-hexopyranosyl)-.
Diffusion model, 51:106 21:304
120 SUBJECT INDEX
3,4,6-tri-O-benzoyl-2-deoxy-~-arubino-hex- Enthalpy
I , crystal structure, 43:262 of activation
Enkephalins, effect on glycosylation, 40:347, of hindered rotation, 23: 198-199
350 of mutarotation of o-glucose, 24:53
Enofuranose of hydrogen bonding, 25:98
6-chloro-5,6-dideoxy-5,6-difluoro- I ,2-0- Entropy
isopropylidene-3-O-methyl-a-~-.qdo- of activation
hex-5- for acid-catalyzed hydrolysis of
(E) isomer, I3C-NMR data for, 46: 176 furanosides, 2 2 4 0
(Z) isomer, I3C-NMR data for, 46: 1 76 in hydrolysis of pyranosides, 2 2 3 3
5,6-dideoxy- for mutarotation of o-glucose, 24:37,53
6,6-difluoro- 1,2-O-isopropylidene-a-~- of hydrogen bonding. 2 5 9 8
xylo-hex-5- Envelope conformation, of furanoid sugars,
3-O-benzyl-,C-NMR data for. 46: 175 26: 109
3-O-methyl-,I3C-NMR data for, 46: 176 Enzyme inhibitors
1,2-O-isopropylidenehex-5- active-site-directed irreversible, 29:2-3
6-chloro-5,6-difluoro-3-O-rnethyI-a-~- low molecular weight, research, Japan,
xylo-, IH and I9F-NMR data for, 48: 13-14
46: 154 polysaccharide sulfates as, 29:336
6,6-difluoro-3-0-methyl-a-o-ribo-, H Enzyme-metal-ion complexes, catalytic
and I9F-NMR data for, 46: 154 activity of, 28:423
6,6-difluoro-3-0-methyl-a-~-.~ido-, H Enzyme Q, in starch synthesis, 34:6
and I9F-NMR data for, 46: 154 Enzymes, see also specific enzymes
6,6-difluoro-3-0-rnethyl-~-~-*ylo-.IH acting on pectic substances, -579-102
and I9F-NMR data for, 46: I54 active site probing, 50:13-14
Enol formation, mechanism of, 26:6 active sites of, 23:296, 298
Enolide, 1p,5,1 la,l9-tetrahydroxy-3b-O-a-~- affinity chromatography purification,
rhamnopymosyl-5P. 14b card-20(22)-, 39:441443
crystal structure, 43:26&265 in alginic acid synthesis, 26:407
Enones, formation of, 46:326 analytical methods utilizing, 30:279-284
Enonolactones Basidiomycetes, glucan degradation by,
2-acylamido-hex-2-. 50:169-1 70 30:361,363-364,367
p-elimination, 50:162-165 in biodegradative hydrolysis of
catalytic hydrogenation, 50:170-1 73 galactomannans, 31:256
Enopyranose, 1,4,6-hi-O-acetyl-2-(N- biosynthesis
acetylacetamido)-2,3-dideoxy-cr-o- of adenosine cyclic 3,5-phosphate in.
erythro-hex-2-, crystal structure, 30:224
43:243-244 guanosine 5-tetraphosphate in, 30:225
Enopyranosides of dexhans, 30:418433
ethyl 4,6-di-O-acety1-2,3-dideoxy-a-~- of tylosin, 3 5 8 4
erythro-hex-2-, crystal structure, 43:229 bound in plant cell-walls, 42:300-302
in synthesis of branched-chain sugars, bovine spleen, dextran degradation by,
4297-98 30:397
Enopyranos-2-ulose, 1,6-anhydro-3,4-dideoxy- in catabolism of starch and glycogen,
P-o-g&cero-hex-3-, 47:338 30:285-302
Enterobacterial common antigen in cellulose synthesis, 26:323-324, 327, 386
f.a.b.-mass spectrometry, 4 5 3 4 classification of metal-dependent, 28:423
perdeuteriomethylated, f.a.b.-mass coffee-bean, in galactomannan structure
spectrometry, 45:69 study, 31:271-274
structure, on f.a.b.-mass spectrometry. 45:69 D-, 2 5 9
130 SUBJECT INDEX
I3C-NMR data for, 46: 173 effect of catalyst on preparation of, 26:200
'H- and "F-NMR data for, 46: 144 hydrolysis of, 26:204
l-deoxy-l-fluoro-2,3:4,5-di-O- preparative column chromatography of
isopropylidene- hydrolysis products, 26:233
13C-NMR data for, 46: 173 2,3:4,5-di-O-rnethylene-P-o-, 26:245
'H- and I9F-NMR data for, 46: 144 1 -0-acetyl-2,3:4,5-di-O-isopropylidene-~-o-,
esters of, 22:292 conformation of, 26:226
taste properties, 45:254 3-0-acetyl- 1,2:4,5-di-O-isopropyli-dene-P-
1-deoxy-1-fluoro-p-o-, synthesis, D-, conformation of, 26:225
38:209-210 3-O-m-~-glucopyranosyl-p-~-, crystal
I ,2:4,5-di-O-isopropylidene-o-, mass structure bibliography, 38:445446
spectrum of, 21:76 3-O-m-o-glucopyranosyl-o-, see Turanose
2,3:4,5-di-O-Isopropylidene-o-, mass 5-O-~-glucopyranosyl-o-,22:230
spectrum of, 21:76 1,2-O-isopropyIidene-p-D-, 26:203
4,5-di-O-acetyl- 1,2-O-isopropylidene-3-0- 2,3-O-isopropyIidene-p-~-, 26:204, 242
methyl-p-o-, conformation of, 26:224 conformation of, 26:225
2,3:4,5-di-O-benzyIidene-p-~-, 26:244 2,3-oxazolidine-2-thinone-o-, 22:280
I ,2:4,5-di-O-cyclohexylidene-o-, I-S-ethyl-] -thio-, 22:28 1
26:244245 1,3,4,5-tetra-U-acetyl-p-o-. 22:250
1,2:4,5-di-O-isopropylidene- 1,3,4,5-tetra-O-benzoyl-p-~-, ammonolysis
3-O-methyl-p-~-,reaction with of. 31:91
butyllithium, 39:145 1,3,4,5-tetra-O-methyl-p-~-, 22:275
3-O-p-tO-lylSUlfOnyl-p-D-, fluorination, h-thio-p-~-.taste properties, 45252
38:222 ~,4,5-tri-~-acety~-2,3-O-isopropylidene-~-~-
2,3:4,5-di-O-isopropylidene- , crystal structure bibliography, 37:398
1-O-methyl-P-o-, reaction with 3,4,5-tri-O-acetyl- 1,2-O-isopropyhdene-p-~-
butyllithium, 39:144 , conformation of, 26:224
1 -O-(methykulfonyl)-p-D-, fluorination, P-D-Fructopyranose calcium chloride
38:210 dihydrate, crystal structure bibliography,
1-O-(tetrahydropyran-2-yl)-P-o-, reaction 32:359
with lithium diisopropylamide, o-Fructopyranose o-fructofuranose 2', I :2,I '-
39: 146 dianhydride, from o-fructose in anhydrous
2,3:4,6-di-O-isopropylidene-, 1-O-methyl-P- hydrogen fluoride, 27:94
D-, 26:244 Fructopyranoside, 53:98
1,2:4,5-di-O-isopropylidene-~-~- a-maltosyl p-D-, 22:23 1
conformation of, 26: 1 19,2 18,225 ethyl p-D-,l-[N,N-bis-(2-chloroethyl)
effect of catalyst on preparation of'. phosphoramidate]. 22:246
26:200,202 methyl 5-amino- 1.3-O-benzylidene-5-deoxy-
hydrolysis of, 26:203 p-D-, 23: 146
mass spectrum of, 26:23 1 methyl p-D-,sweetness-structure relation
oxidation of, 26:250 ship, 45249-250
thin-layer chromatography of, 26:234 methyl 1,3-O-benzyhdene-4,5-di-O-
rearrangement of, 26:220 (methylsulfonyl)-P-o-, displacement
structure of, 26:2 16-2 1 7 reactions of, 24: 16 1
crystal structure bibliography, 31:35 I , 367 trimethylsilyl tetra-O-(trimethylsilyl)-o-,
selective hydrolysis, 39: 17 mass spectrum of, 29:48
2,3:4,5-di-O-isopropylidene-P-~-, 26:220, Fructopyranosyl bromide, 1.3,4,5-tetra-O-
242-243 benzoyl-P-o-, 22:262
conformation of, 26: 1 19, 2 19, 226 Fructopyranosyl fluoride
crystal structure bibliography, 31:367 a-o-and p-D-,22:262
148 SUBJECT INDEX
protecting group in, 46: 188- I 89 hydrolysis of, trifluoroacetic acid in,
methyl 2,3,6-trideoxy-2-fluoro- 28: 17
3-amino-P-, IH- and I9F-NMR data for, monohydrate, crystal structure
46: 124 bibliography, 30:45 1
P- 4,6-phosphate, hydrolysis, 39:6 1
3-amino-,13C-NMR data for, 46: I71 reaction with sulfuryl chloride, 33:74.251,
3-benzamid0-4-O-benzoyl-,~~C-NMR 259
data for, 46:171 selective benzylation of, 33:57
3-(trifluoroa~etarnido)-,~~C-NMR data selective chlorination with
for, 46: 17 1 methanesulfonyl chloride, 33:s 1
3-benzamido-P-, 'H- and I9F-NMR data selective esterification of, 33:27-28
for, 46: 125 sulfonylation of, 23:247
3-benzamido-4-0-benzoyl-P-, ' H- and methyl 4-amino-4-deoxy-a-o-, deamination
I9F-NMR data for, 46:125 of, 31:42
3-(trifluoroacetamido)-, 'H- and "F- methyl 3,h-anhydro-
NMR data for, 46: 125 a-D-,crystal structure bibliography,
trifluoromethyl 3,4-di-O-acetyl-2,6- 31:359
dideoxy-a-, IH- and I9F-NMR data 2,4-di-O-methyl-P-~-.23:270, 24: 146
for, 46: 132 2-0-benzyl-P-o-, 24: 196
methyl 2,3,-di-0-acetyl-4,6-dichloro-4,6- methyl 3.4-anhydro-a-o-, 25127, 145
dideoxy-a-o-, reaction with sodium methyl 6-azido-6-deoxy-2-0-p-tolylsulfonyl-
azide, 28:286 a+-, 24: 145
with tributyltin hydride, 28:303 methyl P-11-
methyl 3, 6-anhydro-a-~-,crystal structure catalytic oxidation of, 33:87
bibliography, 30:45 1 crystal structure bibliography, 3k433-434
methyl 2-acetamido- sulfonylation of, 23:248
3,4-di-0-acetyI-2,-6-dideoxy-6-fluoro-a- methyl 2-benzamido-3-O-benzyi-2,4,-6-
D-, preparation, 38:208 trideoxy-4,6-difluoro-~-,preparation,
6-0-acetyl-2- deoxy-a-o-, selective 38:222
sulfation of, 3 3 5 1 methyl 4,6-bis(acetamido)-4,6-dideoxy-a-~-,
methyl 2-(acetoxymercuri)-3,4,6-tri-O- 23:155
acety1-2-deoxy-P-o-, irradiation, methyl 6-bromo-h-deoxy-. a-D-, crystal
38: 190-1 9 1 structure of, 2 5 7 3
methyl a-D- methyl 2-chloro-2-deoxy-
benzoylation of, 23:250 a,p-o-, crystal structure bibliography,
catalytic oxidation of, 33237 31:366
4,6-dideoxy-4,6-di(thiocyanato)-, P-D-, reaction with sulfuryl chloride,
synthesis, 44: 125 28:235
2,3,4-di-O-acety-6-deoxy-6-thiocyanato-, methyl 4-chloro-4-deoxy-2,3,4-tri-O-p-
44: I43 tolylsulfonyl-a-o-, 22: 183
2,3-di-O-acetyl-6-deoxy-6-thio~yanato-4- methyl 6-chIoro-6-deoxy-2,3,4-tri-O-p-
0-p-tolylsulfonyl-, 44: 143 tolylsulfonyl-a-D-, 22: 184
2,3-di-O-acetyl-4,6-di( thiocyanat0)-. methyl D-
44: I43 halogen derivatives of, 22:221
synthesis, 44: 126 reaction with sulfuryl chloride, 33:74
2,3-di-0-benzoyl-4-deoxy-4-thiocyanato-, methyl 4-deoxy-
44:143 4-iodo-2,3-di O-methyI-2,6-di-O-p-
2,3-di-0-benzoyl-4,6-dideoxy-4,6- tolylsulfonyl-a-o-, 23:268
di(thiocyanat0)-, 44: 143 4-iodo-2,3-di-O-methyI-6-O-p-
formation from dithioacetal, 3 2 6 8 tOlylSUlfOtlyl-D-, 23~268
168 SUBJECT INDEX
D- D-, 49:96-97, I 17
acetylation of, effect of borate on, benzoylation with N-benzoyliniidazole,
28:3435 33:43
anhydridation of, 25:233 esterification with p-phenylazobenzoyl
catalytic oxidation of, 33:88 chloride, 33: 15
selective oxidation with mercuric p-toluenesulfonylation of, 33: 14
acetate, 33: 100 sweetness-structure relationship,
with sodium metaperiodate, 33:95 45:257, 274
conformation of, 25: 105, 26:69 taste properties, 45:270
crystallography of, 25:60 2,5-di-O-p-tolylsulfonyl-u-, 23:252
crystal structure bibliography, 30:450 displacement reactions of, 24: 149
methyl ethers, separation of, 30:2 1 L-, catalytic oxidation of, 2S:261
determination in blood by gas-liquid 2-S-benzoyl-5-O-methylsulfonyl-2-thio-
chromatography, 28:57 I>-, 49: 153
from o-fructose, 22:232,283 2-0-
from o-glucose and its conversion into u- (p-bromopheny1sulfonyI)-u-, 5-nitrate,
fructose, 36:53-54 crystal structure bibliography, 31:367
effect of alkali tetraborates on rotation of, (p-bromophenylsulfonyl)-(exo/-o-,
23:36 crystal and niolecular structures of,
hexaacetate, mass spectrum of, 21:89 25:255
hexanitrate, selective denitration, 3 9 5 8 5-O-p-tolylsulfonyl-~-,23:252
reaction with butanal, 39:26 2,5:3,6-dianhydro-,D-, 29246
irradiation, 38: 147-148 preparation of, 33: I3 1
L-ascorbic acid synthesis, 37: 149 ring opening of, 25257
oxidation, chemical, 37: 1 13-1 I5 1,5:3,6-dianhydro-2,4-0-methylene-~-,
fermentative, 37: 112-1 13 25:245
to L-sorbose, in L-ascorbic acid 2,4:3,5-di-0-benzylidene-l,6-dichloro-l,6-
synthesis, 37:9 1-92 dideoxy-o-, 49: 158
radiolysis and free-radical chcmistry, 1.6-dichloro- I,h-dideoxy-u-, 25:256.
37:27,32 49: 158- I59
in mammalian nerve, determination by preparation of, 28:280
gas-liquid chromatography, 28:58 2,5-dideoxy-2,5-diiodo-u-, 49: 149- 150
utilization by yeasts, 32:146, 218 1,4-dideoxy- 1,4-imino-o-, SO: 198
1-deoxy- I ,S-di-0-acetyl-2,3,4,6-tetra-0-mcthyl-~-,
1,1-bis(nicotinamido)-o-,preparation of, mass spectrum of. 29:62
31:88 1,6-di-0-benzoyl-2,4:3,5-di-O-methylene-o-,
1 -C-methyl-I.-, preparation of, 27:242 acetolysis of, 22:13,39:25
1,l -di-C-(p-methoxypheny1)-D-, 1,3:2,4-di-0-ethylidene-
preparation of, 33: 125 selective
5,6-bis-O-(trifluoroacetyl)-i~-,
I -( 2,4-dinitroaniIino)-o-, irradiation. deacylation, 39:29
38: 173 11-
1-(2-methylhydrazino)-~-,preparation of, 5,6-dinitrate, selective denitration,
29:153 39:57
2,5-diamino-l,4:3,6-dianhydro-~-, oxidation, 38:301
deamination of, 31:55 2,4:3,5-di-0-isopropylidene-o-
1,4-diamino, 1,4-dideoxy-3-0-(4-deoxy-4- acetolysis, selective, 39:25
propionamido-a-o-glucopyranosyl-i>-, selective hydrolysis, 39:23
hydrobromide dihydrate, crystal 1,3:5,6-di-O-isopropylidene-2,4-0-
structure bibliography, 38:463 methylene-o-, selective hydrolysis,
1,4:3,6-dianhydro- 39:23
186 SUBJECT INDEX
2-deoxy-3-~-~-~-galactopyranosy~-a-~-cholesterol-3-yl 2,3,4-tri-O-acetyl-P-o-,
mannopyranosyl-a-o-, preparation, 36:82
deacetylation and hydrolysis of, 31: 195 2-d, methyl 2-deoxy-a-D- and-P-D-,
deamination degradation of, 31:234 preparation of, 27: 132
3,4-di-O-acetyl-2-deoxy-p-~-,synthesis, D-
39:35 2-acetamido-2.6-dideoxy-6-fluoro-a-
3,6-di-O-acetyl-2-deoxy-4-U-(tetra-O- benzyl 3,4-di-O-acetyl-, 'H- and "F-
acetyl-a-D- galactopyranosy1)-, NMR data for, 46: 121
synthesis of, 34:25&25 I methyl 7,4-di-O-acetyI-, 'H- and I9F-
3-0-acetyl-2-deoxy-4.6-di-0- NMR data for, 46: 121
(methylsu1fony)-a-o-, displacement methyl 3,4-di-O-methyI-, 'H-and I9F-
reactions of, 24: 160 NMR data for, 46: 121
4,6-0-benzylidene-2-deoxy-p-~-, selective 2-deoxy-2-fluoro-
etherification with 2-chloropropionic methyl 4,6-di-O-acetyl-3-0-benzyl-P-,
acid, 33:55 IH- and I9F-NMR data for, 46:86
4,6-0-benzylidene-2-deoxy-3-0-( tetra-0- methyl 3-0-acetyl-4,6-0-benzylidene-
acetyl-P-o-galactopyranosyl)-a-n-, p-, 'H- and IyF-NMR data for, 46:87
synthesis of, 34:252 methyl 4,6-0-benzyhdene-3-0-methyl-
benzyl2-amino-2-deoxy-6-0-a-~- p-, 'H- and IyF-NMR data for, 46:87
mannopyranosyl-a-o-, deamination methyl 3-0-benzyl-4,6-0-benzylidene-
degradation of, 31:234 p-, 'H- and I9F-NMR data for, 46537
benzyl2,3-di-0-allyl-4-0-benzyl-p-~-. phenyl 3,4,6-tri-O-acetyl-P-, IH- and
hydrogenolysis, 39: 130 I9F-NMR data for, 46:87
benzyl2,3-di-0-benzyl-4,6-0-benzyl idene- tnfluoromethyl 3.4,6-tn-O-acetyl-a-,
p-D-,hydrogenolysis regioselectivity, 'H-and I9F-NMR data for, 46:87
39:128 3-deoxy-3-fluoro-
benzyl3-0-acetyl-2-[henzyl- benzyl p, 'H- and I9F-NMR data for,
oxycarbonyl)amino]-2-deoxy-4.6-di-0- 46:91
(methylsulfony1)-a-o-, displacement benzyl 2,4,6-tn-O-acetyl-P-, 'H- and
reactions of, 24:160 I9F-NMR data for, 46:91
henzyl4-0-(a-~-glucopyranosyluronic methyl 2-0-acetyl-4,6-0-benzylidene-
acid)++-, synthesis of, 33:88 p-, 'H- and "F-NMR data for, 46:91
benzyl4,6-0-benzylidene- 6-deox y-h-fluoro-
p-D-, selective acylation of, 33:20 methyl. 'H- and 19F-NMR data for,
2-( benzyl-oxycarbonyl)amino-2-deoxy-a- 46:96
D-, hydrogenolysis regioselectivity, methyl 2,7,4-tn-O-benzyl-a-, 'H- and
39: 127 '"F-NMR data for. 46:96
benzyl 6 - ~ - p - t o ~ y ~ s u ~ f o n 23:240
y~-~-~-, phenyl, 'H- and IyF-NMR data for,
benzyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy- 46:96
p-D-,selective deacylation, 39:29 p-nitrophenyl p-, 'H- and IyF-NMR
benzyl 2,3.4-tri-O-benzyl-P-~-,oxidation, data for, 46:96
36:72 methyl 2-acetamido-3-0-acety1-2,4,6-
benzyl 3,4,6-tri-0-benzyl-2-0-triflyl-p-~-, trideoxy-4,6-diffluoro-a-, 'H- and
48:124-125 I9F-NMR data for. 46: IS7
bis(benzy1oxy) isopropyl 2,3,4,6-tetra-O- methyl 4-azido-4,6-dideoxy-6-fluoro-a-,
benzyl-a-o-, preparation of, "C-NMR data for, 46: 171
34:258-259 methyl 2-benzamido-2.6-dideowy-6-
butyl 2-acetamido-2-deoxy-P-o-, fluoro-a-
transglycosylation of, 31:5 3,4-di-O-acetyl-, 'H- and "F-NMR data
carha-glucopyranosyl a-D-,synthesis, 48: 7 1 for, 46: 12 1
206 SUBJECT INDEX
3,4-di-O-acetyl-6-bromo-2,6-dideoxy-c~- tolylsulfonyl-3-O-(trimethylsilyl)-,
D-, preparation by Pinner reaction, 44:144
28:257 2,3-di-O-acety1-6-deoxy-4-0-
3-O-acetyl-6-chloro-2,6-dideoxy-4-0- (methylsulfonyl)-6-thiocyanato-,
(methylsulfonyl)-(Y-D-,preparation 44: 144
of, 28:256,33:83 2,3-di-O-acetyl-4,6-dideoxy-4,6-
3-O-acetyl-2-deoxy-a-o-, di(thiocyanat0)-, 44: 144
methanesulfonylationof, 28:256 2,3-di-O-acetyl-4,6-dideoxy-4-
4,6-O-benzylidene-2-deoxy-a-~-and- thiocyanato-, 44:144
p-D-, selective etherification 2,3-di-O-benzoyI-4,6-didexoy-4-
with 2-chloropropionic acid, thiocyanato-, 44: 144
33:55 2,3-(diphenylcyclodiboronate)-4,6-
3,4,6-tri-O-acetyl-2-deoxy-p-~-, phenylboronate, selective cleavage,
nitrosation of, 31:67 3953
methyl 3-acetamido- electro-oxidation of, 29: 117
3,6-dideoxy-a-~-,acylation and formation from dithioacetal,32:68
sulfonylation of, 33:30 gel chromatography of, 2332
3,6-dideoxy-p-~-,reaction with acetyl hydrolysis of, 22:3 1-32,34
chloride, 33:29 trifuluoroacetic acid in, 28: 17
2,4-di-O-acetyl-3,-6-dideoxy-a-~-, methyl derivatives, sweetness, 43262
selective deacylation, 39:29 methyl ethers, taste properties, 49262
2-O-acetyl-3,6-dideoxy-P-~-, reaction mono-and dideoxy derivatives,
with acetyl chloride, 33:29 sweetness-structure relationship,
4-0-acetyl-3,6-dideoxy-P-~-, reaction 45259-260
with acetyl chloride, 33:29 2-O-acetyl-4,6-dideoxy-4-thiocyanto-,
methyl (Y-D- 44: 144
acetals, taste of, 45243 phenylboronate, preparation, 3538, 46,52
2-acetamido-3-O-acetyl-2-deoxy-4,6-di-O- 4,6-phenylboronate 2,3-(diphenyl-
(methylsufonyl)-S~2nucleophilic cyclodiboronate), hydrolysis, 3552
displacement, 44: 125-126 preparation, 35:47
acylation with N-(tri-0- 4,6-phosphate, hydrolysis, 39:6 1
methylgalloyl)imidazole, 33:43 preparation of, 27:101,31:31-32,34:256,
4,6-benzeneboronate, acetylation and 266
benzoylation of, 23:267 reaction with N-bromosuccinimideand
benzoylation of, 23:249 triphenylphosphine,28:249,33:78
sulfonylation of, 23:247,249 with sulfur monochloride, 28:256
2,3-bis(diethylborinate)4,67- with sulfur monochloride in N,N-
ethylboronate, selective cleavage, dimethylformamide,33: 82
3955 with sulfuryl chloride, 28:230-23 1
catalytic oxidation of, 33:88 relative reactivities of hydroxyl groups in,
C Z and C-0 bond-lengths in, 44: 15 335657
crystal structure bibliography, 31:366 selective acetalation of, 33:71
cyclic 4,6-phosphate selective acetylation with acetic anhydride
cyclohexylammoniumsalt, crystal in pyridine, 33:30
structure bibliography, 37:392 selective benzylation of, 3357
4-deoxy-4-(thiocyanato)-, synthesis, selective chlorination
44: 126 with carbon tetrachloride and
4,6-dideoxy-4-thiocyanato-2-O-p- tris(dimethylamino)phosphine,33:79
tolylsulfonyl-, 44: 144 with methanesulfonyl chloride, 33:8 1
4,6-dideoxy-4-thiocyanato-2-O-p- with sulfuryl chloride, 33:73-74
208 SUBJECT INDEX
(Glucopyranosylthioureide)uronamide, Glucopyranuronamide
preparation, 36: 122-123 a-D-, crystal structure bibliography, 32:3S6
(G1ucopyranosylthioureide)uronicacid, 2,3,4- D-, preparation of, 33:201
tri-O-acetyl-N'-p-o-, methyl ester, D-Glucopyranuronate, diaxial and
preparation, 36: 122 axialequatorial processes in p-elimination,
r)-Glucopyranosyltoluene, surface activity of, 29:258-265
25:256 Glucopyranuronic acid
Glucopyranosyl 2,4,6-trimethylbenzoate. a- and p-D-. 1-esters, preparation, 36: 106
2,3,4,6-tetra-0-acetyI- (Y-D-, calcium bromide salt trihydrate, crystal
a-D-,deacetylation, 39:34 structure bibliography, 34:347
P-D-, deacetylation, 39:34 D-
9-(P-o-Glucopyranosyluronamide)adenine, methyl ester. preparation, 36:59, 64
preparation, 36: 129 structure of, and lactone, 33:190
1 -(~-~-Glucopyranosyluronamide)cytosine, 3,4-di-O-acetyl-l,2-0-[ I -(4-methyl ester,
preparation, 36: 129 preparation, 36: 102
(Glucopyranosyluronamide)thiocarbamate, 1-0-acyl-a- and-p-o-, kinetics of p-D-
preparation, 36:123 glucosiduronase action, 36: 1 12
(Glucopyranosyluronamide)thiosemicarbazide, 1-0-anisoyl-a- and-p-o-, preparation,
derivatives, preparation, 36: 123 36: I08
(Glucopyranosyluronamide)thiourea, 1 -0-benzoyl-a- and-@+-, preparation,
derivatives, preparation, 36: 123 36: 108
Glucopyranosyluronic acid I -0-(1 8p-glycynhet-30-yl)-o-, preparation,
2-acetamido-2-deoxy-ol-o- 36:109-110
ester of uridine 5'-pyrophosphate, 1 -0-(3-carboxypropanoyl- 18P-glycynhet-
isolation of, 28:327 30-yl)-p-o-, preparation, 36:109-110
methyl ester, ester of uridine 5'- I -0-(5-hydroxyindol-3-ylacetyl)-p-~-,
pyrophosphate, preparation and chromatography, 36: 108
reduction of, 28:355 l-O-(indol-3-ylacetyI)-P-~-,
o~-D-, ester of uridine 5'-pyrophosphate, chromatography, 36: 108
decarboxylation of, 28:385 I-0-indomethacin-pa-, synthesis, 36: 104,
enzymic preparation of, 28:343 Ill
isolation of, 28:326 I -0-(N-acylaminoacyl)-tri-~-benzyl-p-o-,
4-0-( ~-D-Glucopyranosy~uronic acid)-D- benzyl esters, preparation, 36: 1 13
glucaric acid, hydrolysis of, rate of, 22:78 I -0-[N-(rerr-buty1oxycarbonyI)-~-alanyl]- p-
(Glucopyranosyluronic acid)-2-4- D-, preparation, 36: I 14
dioxothiazolidine, preparation, 1-0-veratroyl-a- and-p-o-, preparation.
36:123-124 36:lOS
Glucopyranosyluronic acid epitope, 4- tetra-0-acetyl-u-, methyl ester, preparation,
acetamido-4-deoxy-2-0-methyl-~-1.- 3659
fucopyranosyl-( 1+4)-p-o-, 51:2 18 1,2,3,4-tetra-O-benzyl-a- and-@+, benzyl
Glucopyransoylamine,2-acetamido-N-( I - ester, preparation, 36:78
aspart-4-oyl)-2-deoxy-p-o- 1,1 '-thiobis(methy1 2,3,4-tri-0-acetyl-P-~-,
analogs, synthesis, 43: 140-141 dimethyl ester, preparation, 36:99
elongation of 2,3,4-tri 0-acetyl-D-, methyl ester,
cabohydrate chain, 43: 155-156 preparation, 36:60,62
peptide chain, 43: 152-154 2,3,4-tri-0-acetyI-l-O-
synthesis, 43:137-138, 140 acetyl- 1-0-4-methoxybenozyl-p-~-,
Glucopyransoyl isothiocyanate, 3,4,6-tri-0- methyl ester, preparation, 36: 106
acetyl-2-deoxy-2-thicoyanato-a-o.24: acyl-o-, methyl esters, proton magnetic
209 resonance spectroscopy, 36: 1 I &I I 1
220 SUBJECT INDEX
and biosynthesis, 37: 182-1 89, 2 18-22 1 polarography of, 29:133, 150-151
and glycosylation, 37: 184-187 radiation chemistry, 37:32-33
and metabolism, 37: 182, 218-22 I separation from glycolaldehyde as
role, 37:2 13-2 14 trimethylsilyl oxrmes, 28:3 I
spatial conformation, 37:206-2 12 Wittig reaction with, 27:245, 288-289
structure of glycoprotein, 37: 157-223 Glyceric acid
antenna and variable fraction, 37: 170, 2-deoxy-2-fluoro-, 22:206
172-173, 177 3-0-phosphono-
core and invariant fraction, 37: 170 u-, calcium salt trihydrate, crystal structure
glycan-protein linkages, 37: 164- I70 bibliography, 30:447
N-acetyllactosaminic type, 37: 171, 173, in photosynthesis, 32:7-8
178-179 trimethylsilylated, mass spectrometry of.
n-glycans and isoglycans, 37: 170 29:80
oligomannosidic type, 37:171-176, 178 Glyceride, 0-a-u-galactosyl-, occurrence,
Glycenoses, 23:234 37:322-328
Glyc-3-enuloses, l-bromo-l,3,4-trideoxy-, Glycerol
synthesis of, 27:295 I - and 2-phosphates. phosphono migration
Glyceraldehyde, 46:32 1 in. 33: 108
carbon monoxide elimination by radiation, 1.2-anhydro-3-deoxy-or -,sulfonylation of,
37:14 23:239
composition in solution, 42:20, 3 I , 37 2-C-(hydroxymethyl)-,synthetic and
D- formose component, 29:209
(+)-,synthesis of, 21:17 cluster ions, 45:29
configurational correlation with L-serrne, 3-deoxy-
27:207 I-O-p-tolylsulfonyl-o~-, 23:239
configuration of, 26: 13 2-O-p-tolylsulfonyl-o~-, 23:239
from u-fructose in liver, 34:292--293 1 -deoxy- 1 -fluoro-
diethyl dithioacetal, physical constants of, D-, preparation, 38:210
32: 102 L-, selective phosphorylation with
gel chromatography of, 2 5 3 I dibenzyl phosphorochloridate, 33:50
3-phosphate hydrate, carbon- 13 nuclear 2-deoxy-2-fluoro-, synthesis, 38:237
magnetic resonance spectroscopy, 6-deoxy-6-sulfo-a-o-glucopyranosy1-( 1 4 I )-
41:53 D-, rubidium salt, crystal structure
reaction with 1,3 dicarbonyl compounds, bibliography, 31:366
45: 13 o-galactosides, 37:3 12-3 16. 360-362
dehydration to pyruvaldehyde, 28: 174 1,2-dithio-. in dithioacetal preparation, 32: 19
acidic conditions, 46:278-279 enzymic determination of, 30:282-283
2-deoxy-2-fluoro-o~-,22: 199 ester of cytidine 5'-pyrophosphate, isolation
synthesis, 40: 105 of, 28:334
DL- esters, acyl migration in. 33: 107
dimer, crystal structure bibliography, ethylboronate, structure, 35:43
31:359 gas-liquid chromatography of, 28:57,91
reaction with ammonia, 25:325 inhibitory effect in pectinesterase, 33:337
gas-liquid chromatography of, 28:96 manufacture from yeast and sugar,
high-temperature transformation, in alkali 32:127-128
conditions, 46:284 as matrix for f.a.b.-mass spectrometry,
kinetic currents in polarography of, 29: I36 45:25-26
2,3-0-isopropylidene-~-, carbohydrate 2,2'-0-methylenebis-
substrate, 40: 120-122 1 -deoxy- I -fluoro-L-, 'H-and I9F-NMR
3-phosphate, radiolysis, 37:42 data for, 46: 158
236 SUBJECT INDEX
4-0-(2-acetamido-2-deoxy-o- Gulono- I ~
H- and
dideoxy-4-fluoro-6-O-trityl-01-, ' by o-gulono- 1,4-lactone reduction.
"F-NMR data for, 46: 1 19 3 8 ~ 15-3
3 16
2-deoxy-2-fluoro-p-~-,48: 132 preparation, 38:293-294
2-flUOrO-OI-D-, 48:13 1-132 halogen derivatives of, 22:217
methyl cx(and P)-D-, hydrolysis of, 22:45 synthesis of, 24:247
methyl 4-acetamido-4,6-dideoxy-01-~-, 6-deoxy-
23:187 ~-,21:173,178, 181
methyl 3-acetylation 3,6-dideoxy-a-~-, L-, 21:178
acetylation of, 33:30 preparation, 38:3 16
methyl 2,3-anhydro- 2,3-O-isopropylidene-~-composition in
OI-D-, 25~127,145-146 aqueous solution, 42:59
4,6-benzylidene-o-, 25: 116 4-thio-~-composition in aqueous solution,
methyl D-, effect of calcium chloride on 42:53
specific rotation of, 21:230 2,6-diamin0-2,6-dideoxy-o-, 22: 14 I
methyl 6 - d e o x y - a - ~ ~synthesis,
-, 40:h9 I ,2:5,6-di-O-isopropylidene-
methyl 2-deoxy-3,4,6-tri-O-p-tolylsufonyl-01- OI-D-, 24:247
D-, 23:272 D-, selective hydrolysis, 39: 15
methyl 4,6-O-benzylidene-, hydrolysis of, 2,3:5,6-di-O-isopropylidene-o-, preparation,
34:202 38:316
Gulopyranosiduronic acid, methyl p-0-, L-
ammonium salt, preparation, 36:73 derivatives of cyclic acetals, Table, 34:234
Gulopyranosse, 1,6-anhydro- preparation, 37: 109-1 10,38:290-29 1
p-D-, sulfonylation of, 23:252 synthesis of, 33:88
2,3-di-O-p-tolylsuIfonyl-~-u-, 23:252 2,3-O-isopropylidene-o-,preparation, 38:3 16
2,3,4-~-0-p-tolylsulfonyl-~-u-, 23:252 pyranose form, 42:63
Gulopyranosyl chloride, 6-deoxy-2,3-0- stability in solution, 42:26
isopropylidene-4-O-methyl-p-~-, reaction Guloseptanose, 4,5-di-O-acetyl- I ,2-0-
with base, 39: 147-148 isopropylidene-3-O-methyl-01-~-, crystal
Gulopyranosyluronic acid, P-L-, ester of structure bibliography, 31:3 53
guanosine 5'-pyrophosphate, isolation of. Guluronan, L-, crystal structure bibliography,
28:320 33:403
Gulopyranuronic acid, D-, methyl 01- and p- i.-Guluronan lyase, 44: 192-1 94
glycosides, preparation, 36:72 Guluronic acid
Gulose 2,3-diamino-2.3-dideoxy-~-, biosynthesis,
2-acetamido-2-deoxy-D- composition in 44:29&298
aqueous solution, 42:47, 67 01-L-, 47:24-25
2-amino-2-deoxy-u-, 22: 13 I , 14 I. 24: I 12 complexing. 47:32
derivatives, synthesis of, 22: 138 L-
3-amino-3-deoxy-o-, 22: 131 of alginic acid, 35:8, 10
2-amino-2,6-dideoxy-o-, 22: 141 biosynthesis, 44:296-298
3,6-anhydro-~-composition in aqueous Gum arabic, 22:5. 24:34&341
solution, 42:58 acetolysis of carboxyl-reduced, 31: 199
in aqueous solution, composition, 42:63 as a-L-arabinofuranosidase substrate,
OI-D-, effect of alkaline-earth metal salts on 42:390,392
specific rotation of, 21:230 antitumor activity of, 32:253. 266
D- structure, 24:343, 346, 41:8
calcium chloride complex, mutarotation enzymic analysis, 44:247
of, 23:34 Gums, 22:5,24:333-379
derivatives of cyclic acetals, Table, Acacia, 24:343-348
34:234 Acacia arubicu, 24:342, 345-346
260 SUBJECT INDEX
isopropylidene- 3,4.5-tri-0-acetyl-2,6-anhydro-o-lyxo-.
cU-D-X,VlO-, 24~255 methyl ester, preparation, 36:61. 78
a - ~xylo-,
- synthesis by Wittig reaction, Hex-2-enono- I ,4-Iactone
21:293 2-acetamido-2,3-dideoxy-
3,5-0-benzylidene-6-deoxy- 1,2-0- o-erythro-, crystal structure bibliography,
isopropylidene-, C U - D - X ~ ~ O22:202
-. 38:437
2.3,5-tri-O-acetyl-l,6-anhydro-P-~-urnhino-, D-threo-, crystal structure bibliography.
preparation of, 34: 156 37:380
Hex-3-enofuranoside, 4,6-dichloro-4.6- 5,6-O-isopropylidene-~-threo-. crystal
dideoxy-a-o-galactopyranosyl1,4,6- structure bibliography. 38:44044 I
trichloro- 1,3,4,6-tertradeoxy-2.3-di-O- o-erythro-. see u-Erythorbic acid
sulfo-P-D-g[ycero-, physical properties I -threo-, see Ascorbic acid, I.-
of, 33:294 2-mesyslates, 50: 167
dideoxy-2.3-di-O-sulfo-a-~- 2-O-benzyl-3-deoxy-~-threo-. preparation of,
galactopyranosyl 1,4,6-trichloro- 33:220-22 I
1,3,4,6-tetradeoxy-P-~-g[ycero-. Hex-2-enono- 1,j-lactone
preparation of, 33:261 2,4-di-0-benroyl-3,6-dideoxy-i.-eryrhro-,
Hex-4-enofuranoside, methyl 5,6-dideoxy-2,3- 50: 164
0-isopropylidene-P-n-eryfhro-, reaction 2,4,6-tri-0-benzoyl-3-deoxy-1~-erythro-,
with bromine in chloroform or carbon synthesis. 49:90-91
tetrachloride, 28:269 Hex-2-enono- 1,5-lactone, 2,3,4,6-tetradeoxy-
Hex-5-enofuranoside m-glycero-. see Parasorbic acid
5,6-dideoxy-2,3-O-isopropylidene-P- v-riho-, Hex-2-enopuranoside
preparation of, 31:56 cholesteryl4.6-di-0-acetyl-2,3-dideoxy-a-o-
D-riho-, methyl 5,6-dideoxy-6,6-difluoro- erythro-, 24:215
2,3-O-isopropylidene-a- 6-deoxy- 1,2:3,4-di-O-isopropylidene-a-~-
13C-NMR data for, 46: 176 galactopyranos-6-yl4,6-di-O-acetyl-
'H- and I9F-NMR data for. 46: 154 2,3-dideoxy-a-o-etyhro-, 24:2 15
methyl 5,6-dideoxy- 4,6-di-0-acetyI-2,3-dideoxy-i~ervthro-hex-
2,3-di-O-p-to~ykulfony~-a-~-arabino-, 2-enopyranosyl4,6-di-O-acetyI-2,3-
reaction with iodine trifluoroacetate, dideoxy-o-ecvthro-. 24:2 16
28:273 ethyl 4,6-di-O-acetyl-2,3-dideoxy-a-~-
with nitryl iodide, and with iodien erythro-, 24:2 15
azide, 28:270-27 I , 299 methyl 2-azido-4,6-0-benzylidene-2.3-
6-nitro-2,3-di-O-p-tolylsulfonyl-a-~- dideoxy-a-n-eythro-, 24:244
arubino-, preparation of, 28:299 methyl 4,6-di-U-acetyl-2,3-dideoxy-a-o-
2,3,4,6-tetra-0-acety~-a-~-glucopyranosyl erythro-, 24:232
1,3,4-tri-0-actyl-6-deoxy-P-o-/hre~~- threo-, 24:215
preparation of, 33:264 methyl 4,0-acetyl-2,3,6-trideoxy-3-C-
reduction of, 33:266 methyl-L-threo-, 24:246
2-Hexenoic acid, cis-4,5-epoxy-, resolution, methyl 4,6-O-benzylidene-
40:114 3-cyano-2,3-dideoxy-a-~-y!~rhro-,
4-Hexenoic acid 24:246
3(R)-hydroxy-3(R)-methyl-, preparation, 3-deoxy-2,S-methyI-2-thio-a-o-ey/hro-,
40:114 24:244
trans-3-hydroxy-3-methyl-, methyl ester. 3-deoxy-2,S-phenyl-2-thio-a-o-enThro-,
precursor for sugar synthesis, 40:2 I 24:244
274 SUBJECT INDEX
2,3-Hexodiulose 1,2:5,6-di-O-isopropylidene-a-~-
1-deoxy-o-erythro-, 25:343 ribo-, cis- and trans-, preparation.
alkaline degradation of, 28:196 38:247-248
dehydration of, 28: 194 xylo-, cis- and trans-. preparation,
from D-fructose dehydration, 28: 1 79- I80 38:247-248
preparation of, 28: 168-1 69, I94 D-
4-deoxy-o-g~cero-,25:343 3-deoxy-3-C-(difluoromethylene)- 1,2:,5,6-
preparation of, 28: 168-169 di-0-isopropylidene-a-
2,5-Hexodiulose ribo-. IH- and I9F-NMR data for,
1,4:3,6-dianhydro-o-rhreo-, 25:26 1 46:141
o-threo-, 22:284 xylo-. 'H- and "F-NMR data for,
composition in aqueous solution, 42:38 46:141
dehydration of, 28: 186 3-deoxy-3-C-(fluoromethylene)- 1,2:5,6)-
preparation, 37: 140 di-0-isopropylidene-a-, ribo-, 'H-
L-threo-, dimer, crystal structure and IyF-NMR data for, 46:140
bibliography, 37:387 3-deoxy-3-C-(fluoromethylene)-I .2:5,6-
Hexodiulosonic acid, o-thre0-2,5-, 46:34 di-0-isopropylidene-a-, xylo-. 'H-
composition in aqueous solution, 42:40 and "F-NMR data for, 46: 140
2,3-hexodiulosonic acid, threo-, polarog-raphy L-ribo-
of o-phenylenediamine condensation 3-acetamido-2,3,5,6-tetradeoxy-5-
products, 29: 154 fl~oro-@-,'~C-NMR data for, 46: 17 I
2,5-Hexodiulosonic acid, o-threo- 3-acetamido-2,3,5,6-tetradeoxy-5-
methyl ester, preparation, 37: 143 fluoro- l-O-(4-nitrobenzoyl)a-, P-
reduction, 37: 145 'H- and I9F-NMR data for, 46: 128
preparation, 37: 137-140, 145-146 methyl 3-acetamido-2,3,5,6-tetradeoxy-
reactions, 37: 142-143 5-flUOrO-P-, IH- and I9F-NMR data
reduction, 37:14&145 for, 46: 128
structure, 37:141-142 1 -0-acetyl-2.3,5,6-tetra-O-henzoyl-4-
2,3-Hexodiulosono- 1,4-lactone, L-thrro-.2-( p - deoxy-4-fluoro-P-
bromophenyl)hydrazone, crystal structure galacro-, 'H- and I9F-NMR data for,
bibliography, 37:386 46: 143
Hexofuranose gluco-, 'H- and "F-NMR data for,
1,5-anhydro-, formation of, 34:88 46: 143
1,6-anhydro-, 7:37-52 2-deoxy-, 2-fluoro-, IH- and "F-NMR data
(6-acetamido-2,3-di-O-acetyl-5,6-dideoxy- for, 46:99
P-D-xY~o-,preparation of, 34: 15 1 3-deoxy-
analogs, 34: 146-1 5 1 3-C-(difluoromethylene)- 1,2:5,6-di-O-
complex formation with, 34: 154 isopropyhdene-a-o-rzbo-,
and derivatives, Table, 34: 177 preparation, 38:249
formation and preparation of, 34388. 3-C-(difluoromethylene)-l,2:5,6-di-0-
151 isopropyhdene-a-o-xv[o-,
by pyrolysis of monosaccharides, preparation, 38:249
34:46 3-C-(fluoromethyl)-I ,2:5,6-di-0-
properties of, 34: 153-1 55 isopropylidene-cu-D-ribo-,cis- and
reactions of, 34: 155-1 57 trans-, preparation, 38:247-248
5,6-anhydro-, 25: 160-163, 179 3-C-( fluoromethyl)- 1,2:5,6-di-0-
3,6-anhydro-5-deoxy- 1,2-0-isopropylidene- isopropylidene-a-o-xylo-,cis- and
~-D-I$o-, 23:241 trans-, preparation, 38:247-248
preparation of, 28:271 3-deuterio- 1,2:5,6-di-O-isopropylidene-a-
3-C-(chlorofluoromethylene)-3-deoxy- o-ribo-, preparation of, 28:303
280 SUBJECT INDEX
I crystal
1(4),3(6)-(R,R)-di-S-oxide,
structure, 43:341
Idaric acid, 2,5-anhydro-o-, 25190 1,6-di-0-acetyl-2,4:3,5-di-O-methyl-ene-~-,
preparation of, 33: 119 22:15
ldono- 1,4-lactone, 2-amino-2-deoxy-~-, 1,6-di-O-benzyl-2,4:3,5-di-O-methyl-ene-~ ,
deamination of, 31:58 acetolysis of, 22:15
Iditol 1,2:5,6-di-O-isopropyIidene-o-,3,-4-
3-acetamido- 1,2:5,6-di-O-isopropylidene-~-, trithiocarbonate, acetobrominolysis,
22:133 39:114
1-amino-1,5-anhydro- I-deoxy-L-, 23: 137 di-0-isopropylidene-o ,monobenzoate,
preparation of, 34: 150 22:118
I-amino-l,6-anhydro- 1-deoxy-L-, 23: 156 1,2:5,6-di-O-isopropylidene-3,4-dithio-o-,
preparation of, 34: 150 acid hydrolysis of, 32:44
1-amino- 1 -deoxy-o-, deamination of, 31:60 2,4:3,5-di-O-methylene-~ , acetoiysis of,
1,4-anhydro-r-, catalytic oxidation of, 22:13
25261 L-, anhydridation of, 25:233
1,6-anhydro-r- 3,4-S-kopropylidene-3,4-dithio-o-,
crystal structure bibliography, 34:350 preparation of, 32:44
infrared spectrum of, 25250 tri-0-acetyl- 1,5-anhydro-5-deoxy-5-C-[(S)-
2,5-anhydro-~-,29243 phenylphosphinyl]-L-, physical
1,2-bis(acetamid0)-3,4,5-tri-O-acetyl-2,6- properties of, 42:191
anhydro- 1,2-dideoxy-o-, 23: 160 ldofuranose
crystallography of, 25:60 3,6-(acetylepimino)-3,6-dideoxy-1,2-0-
D-, 21:17 isopropylidene-P-L-, crystal structure
conformation of, 26:69 bibliography, 30:452
crystal structure bibliography, 30:450 5-amino-5-deoxy-l,2-0-isopropylidene-~-~-,
1,6-diamino- I ,5-anhydro-l,6-dideoxy-~-, 23:135
23:137 5-amino-3-0-benzyl-5,6-dideoxy- 1,2-0-
1,4:3,6-dianhydro- isopropylidene-P-L-, 23: 139
2,5-0-benzoyl-2,5-dithio-~-, 49: 153 3,6-anhydro-5-deoxy-5 -fluoro- 1,2-0-
D-, 25246 isopropylidene-
2,5-dideoxy-2,5-(dithiocyano)-~-, 49: 153 a-L-,proton magnetic resonance
2,5-di-O-p-tolylsulfonyl-r-, displacement spectroscopy of, 27532
reactions of, 24: 149 p-L-,preparation, 38:221
L-, 25:260,49:96 3,6-anhydro-5-deoxy-5-iodo-l,2-0-
catalytic oxidation of, 25261 isopropylidene-P-r-, preparation of,
infrared spectra of, and nitrates, 25:252 28:27 1
nuclear magnetic resonance spectra of, I ,5-anhydro-2,3-di-O-benzyl-6-O-trityl-a-~-,
and derivatives, 25254 24:171
2,3:4,5-dianhydro- 3,5-anhydro-l,2-0-isopropylidene-
D-, 24:168,49:124-125 p-L-,conformation of, 26: 122
proton magnetic resonance spectroscopy 6-O-trityl-p-~-,24:114
of, and esters, 27:64 5,6-anhydro- 1,2-0-isopropylidene-P-~-,
1.6-di-O-(methyIsulfonyl)-~-, cytostatic 25112
activity, 28:7 6-azido-5,6-dideoxy-5-iodo- 1,2-0-
2,5-dideoxy-2,5-diiodo-~-, 49: 149-1 50 isopropylidene-P-L-
2,5-di-O-acetyI-l,4:3,6-dianhydro- 1(4);3(6)- crystal structure of, 25:74,30:452
dithio-D- preparation of, 28:271
disulfoxide, crystal structure bibliography, S-(benzylamino)- 1,2-0-cyclohexylidene-5-
34:372 deoxy-L-, 23:141
SUBJECT INDEX 303
Idofuranurono-6,3-lactone(continued) 1,4-anhydro-
I3C-NMR data for, 46: 170 2,3-di-O-benzyl-6-O-trityl-P-~-,
24: 171
'H-and "F-NMR data for, 46: 116 2,3,6-tri-O-methyl-i-, synthesis, 39: 165
1,2-O-isopropylidene- 1,6-anhydro-
I3C-NMR data for, 46: 170 p-0-
'H- and "F-NMR data for, 46: 116 catalytic oxidation of, 33:90
1,2-0-isopropylidene-P-~-, preparation, per-0-substituted, 34:77
36:74 3-deoxy-3-fluoro-P-o-, specific rotation
Idonic acid of, 34: 135
2-amino-2-deoxy-o-, deamination, 25: 190, 3-deoxy-3-nitro-P-o-, preparation of,
31:58,33:119 34:105, 126
2,4:3,5-di-O-benzyIidene-L-, preparation and 2,4-di (benzylamin0)- 2,3,4-trideoxy-3-
structure, 37: 129 nitro-p-o-, preparation of, 34: 106,
L-, conversion into ~-xylo-2-hexulosonic 126
acid, 37:134-137 2-Sbenzyl-2-thi-P-~-, preparation of,
preparation, 37:108-109, 120, 129-133 34:136
Idono-l,5-lactam, 5-amino-5-deoxy-~-,23: 166 5-(benzylamino)-5-deoxy-~-,23: 141
Idonolactone, 2-amino-2-deoxy-o-, 5,6-bis(acetamido)
deamination, 25: 190,33:119 1,6-anhydro-5,6-dideoxy-P-~-, 23: 176,
Idono- 1,4-lactone 199-200
3,6-anhydro-~-,25261 2,3,4-tri-O-acetyl- 1,6-anhydro-5,6-
L-, irradiation, 37: 123 dideoxy-P-L-, mass spectrum of,
Idopyranose 23:205
OL-D-, 45:74 carba-P-DL-, 48:34
D-, orientation of hydroxyl groups for, in 5-deoxy-5-phosphino-and 5-phosphinyl-~-
4 C , ( ~conformation,
) 45:75 bond lengths for pyranoid ring of, 42: 165
Idopyranose Cremer-People puckering parameters for,
2,3,4,-triamino- 1,6-anhydr0-2,3,4-trideoxy- 42: 164
P-D-, preparation of, 34: 126 ORTEP representation, 42:163
5-acetamido- synthesis and structures of, 42: 145-155
1,6-anhydro-5-deoxy-P-L-, 23: 175 5.6 diamino- 1,6-anhydro-5,6-dideoxy-P-~-
2,3,4-tri-O-acetyl- 1,6-anhydro-5-deoxy-P- formation of, 34: 149
L-, mass spectrum of, 23:204 mass spectrum of, 23: 176
6-acetamido-2,3,4-tri-0-acetyl-1,6-anhydro- 2,6-diamino-2,6-dideoxy-~-, 23: 168
5-deoxy-P-~-,mass spectrum of, 23:203 L-, 3-deoxy-3-fluoro-
a-D- 01 anomer, 'H- and I9F-NMR data for,
conformation in aqueous solution, 26534 46:91
pentaacetate p anomer, 'H- and I9F-NMR data for,
conformation of, 24:58 46:9 1
proton magnetic resonance spectroscopy penta-0-acetyl-
of, 27:23 OL-D-
6-amino- 1,6-anhydr0-6-deoxy- conformation of, 26: 102
p-L-, formation of, 34: 149 in solution, 26:87
L-, 23: 156 preparation and conformation of,
2-amino- 1,6-anhydro-2- deoxy-P-o-, 26:149
preparation of, 34: 122 5-thio-~-,23:217
3-amino- 1,6-anhydro-3-deoxy-P-o-, 1,2,3,4,6-penta-0-acetyI-a-~-, crystal
preparation of, 34: 122, 126 structure bibliography, 37:401
5-amino-l,6-anhydro-5-deoxy-P-~-, 23: 136 5-(phenylphosphinyl)-~-
formation of, 34: 149 mass spectrometry of, 42: 172-1 76
SUBJECT INDEX 305
synthesis, 40:68-69
a-DL-, a-D-, 26: 119
p-DL-, synthesis, 40:69 Lyxopyranosylmethane, bis(ethylsulfony1) a-
p-L-, 25: 154 D-, triacetate, nuclear magnetic resonance
D-, 25: 153 spectrum of, 25:252
methyl p-DL-,synthesis, 40:68 Lyxose
methyl++-, 22:126 2,s-anhydro-
methyl D-, conformation in solution, 26:84 D-
methyl 2,4-di-O-benzoyl-3-bromo-3-deoxy- dialkyl dithioacetal, 25: 198
a-D-,synthesis, 39:112 diisobutyl dithioacetal, 24: 175
methyl 2-O-benezoyl-3,4-di-S-benzoyl-3,4- 3,4-di-p-tolylsulfonyl-~-, diisobutyl
dithio-P-L-, 22: 141 dithioacetal, preparation of, 32:5 1
methyl 4-O-benxoyl-2,-3-O-benzylidene-01- 5-seleno-~-,dimethyl acetal, 25:205
D-, reaction with triphenylmethyl 5-thio-D-,dimethyl acetal, 25:205
fluoroborate, 39: 110-1 12 p-L-
methyl 2,3-O-isopropylidene-01-~- crystal structure bibliography, 31:363
hydrolysis of, 34:204 taste properties, 45:242
in L-apiose synthesis, 31: 182 5-bromo-5-deoxy-DL-,synthesis of, 28:304,
methyl 2.3-O-isopropylidene-4-O-p- 40:90
tolylsulfonyl-a-o-(or a - ~ ) - , composition in nonaqueous solvents, 42:68
displacement reactions of, 24: 191 D-
methyl tri-0-methyl-a(and P)-D-, mass in aqueous solution, 42:16
spectra of, 21:60 composition, 42:64.66
methyl tri-0-acetyl-a+-, proton magnetic polarimetry, 42:22
resonance spectroscopy of, 27:28 derivatives of cyclic acetals, Table.
methyl 2,3,4-tri-O-acetyl-5-amino-S-deoxy- 34:212
5-N-(methoxy)-, synthesis, 40: 100 dialkyl dithioacetal, reaction withp-
methyl tri-0-benzoyl-a-D-, proton magnetic toluenesulfonyl chloride, 25: 198
resonance spectroscopy of, 27:28 diethyl dithioacetal, partial
Lyxopyranosyl chloride demercaptalation of, 32:67
01-D-, 2,3,4-tri(chlorosulfate), preparation and diisobutyl dithioacetal, reaction with p -
reactions of, 28:235-237 toluenesulfonyl chloride, 3 2 3 1
2-chloro-2-deoxy-01-~-,2,4-di(chlorosulfate), dithioacetal
preparation of, 28:236 reaction with sulfonyl chloride in
Lyxopyranosyl fluoride pyridine, 32:48
D- selective esterification of, 33:4041
3,4-di-O-acetyl-2-deoxy- reaction with sulfuryl chloride, 33:76
2-bromo-, IH- and 19F-NMR data for, synthesis of, 33:93
46:135 halogen derivatives, 22:2 16
2-iodo-, 'H- and IYF-NMRdata for, nonselective spin-lattice relaxation rates,
46: I36 45:148
2,3,4-tri-O-acetyl-a-, IH- and IYF-NMR polarography of, 29: 126
data for, 46: 102 utilization by yeasts, 32:2 15
2,3,4-tri-O-henzoyl-a-, IH- and "F-NMR 5-deoxy-~-,21: 177
data for, 46: 102 5-deoxy-~-,21:17&177
per-O-acetyl-2-deoxy-2-fluoro-p-~-, preparation from dithioacetal of 6-deoxy-
preparation, 38:204 L-galactose, 32:8S
per-0-benzoyl-a-o-, preparation, 38:20 1 3,4-di-O-acetyl-2,5-anhydro-
tri-0-acetyl-a, p-D-,26: 179 aldeh-ydo-o-, and p-nitrophenylhydrazone,
tri-0-benzoyl- preparation of, 28:287-288
a,p-D-, 26: 179 D-,(p-nitrophenyl)hydrazone, 25:202
334 SUBJECT INDEX
Orientation, mechanism of, in plant cell walls, phenyl-, in mass spectrometry, 30:43
26~331-335,338 of sugars, 3:2344
Orosomucoid Osladin
a-o-mannosidase in structural studies of structural features, 45:289
human, 28:445 taste properties, 45:286-287
carbohydrate linkage in, 25:421,444,466 Osones, 11:43-96,21:11
glycopeptides, liquid chromatography Osotriazoles
separation, 46:48 chemistry of, 18:99-121
isolation of carbohydrates from, on conformation of sugar derivatives, 26:
analytical-scale columns, 46:60 71-72
sialylated oligosaccharides, fractionation, N-phenyl-, oligosaccharide acetates, mass
46:46 spectrometry of, 29: 101-103
Orotic acid monohydrate, 43:274 Ospolot, 45:5
Orotidine 5-phosphate, 22:3 12 0-substitution
ORTEP representation of phosphorus sugars, nomenclature, 52: 1 12-1 13
42:163, 183 acyl, 52:112-113
Orthoacetates, of sugars, 21:20 phosphates, 52: 113-1 15
Orthoacetic acid, methyl ester, reaction with phosphinates, 52: 116
ribonucleosides, 22:340 phosphonates, 52: 115-1 16
Orthobenzoic acid, esters of o-fructose sugars, composition in aqueous solution,
derivatives, 22:248 42:4346
Orthoesters Ouabain, octahydrate, crystal structure,
of carbohydrates, 1:77-127 43:264-265
derivatives, formation, aldonolactones Ovalbumin, 44:232,239-240
reaction with alcohols, 50:149-151 a-D-mannosidase action on, 28:437443
of D-fructofuranose, 22:292 aspartamidoglycans from, composition and
of o-fructose derivatives, 22:248 effect of enzymic hydrolysis of,
hydrogenolysis, 39: 127 28:440442
of cyclic, cyclic acetal synthesis, 39:79 glycopeptides, liquid chromatography
as protecting groups, 36: 144 separation, 46:48
1,2-Orthoesters, of acylated sugars, glycoside hen
synthesis from, 34:244,248 I3C-n.mr. spectral reporter regions,
Orthoformic acid, ethyl ester, reaction with 43: 14-1 5
ribonucleosides, 22:340 oligopeptides
Orthoglyoxylic acid, trithio-, triethyl ester, high-mannose, 43: 11-13
formation from dithioacetal, 32:81 hybrid, 43: 1 1-14
Orthosaccharinic acids, and lactones, 22:206 hydrolysis, with trifluoroacetic acid,
Osage orange 46:268
lectin isolation of carbohydrates from, on
carbohydrate-binding specificity, analytical-scale columns, 46:60
35:268-270 oligosaccharides, liquid chromatography
isolation, purification, and properties, separation, 46:4243
35~267 sialylated oligosacchairdes, fractionation,
pigments, structure of, 26: 16 46:46
Osazones Ovarian cysts
chemistry of, 20:139-181 blood-group
of o-fructose derivatives, 22:263 H substance, Smith degradation of,
discovery of, 21:lO 31:209
formation mechanism of, hydrogen isotope substances, 25:426,433,446,452458
effect on, 27: 15 1 glycoproteins, oligosaccharides from, liquid
SUBJEC'T INDEX 395
xylofuranos-3-yl)-5-hydroxy-2,4- Phosphorus
dioxopyrrolidin-3-ylidene]triphenyl-, 32P-labelednucleotides, 22:339
preparation, 38:25 1-252 ring oxygen replacement by, 52: 140-141
[5-(,")-(3-deoxy-3-fluoro- 1,-2:5,6-di-0- starch phosphate content. 51:250, 253
isopropylidene-a-u-glucoft1ranos-3-yl)- in yeast mannan, 23:391
5-hydroxy-2,4-dioxopyrrolidin-3- Phosphorus acid, in nucleotide synthesis,
ylideneltriphenyl- 22:342
preparation, 38:250-25 I Phosphorus compounds
X-ray crystallography, 38:28 1 in deoxyhalogeno, sugar synthesis, 28:280
sugar, synthesis of, 27:295 as solvents for sugars, 27:123
Phosphoric acid Phosphorus halides, replacement of hydroxyl
1,4:3,6-dianhydrohexitolsesters, 49: 130-132 group in carbohydrates by halogen, 22: 184
as solvent for sugars, 27:94 Phosphorus-3 1 NMR spectroscopy, 42: 19-20
Phosphoric esters Phosphorus oxoacid esters, nomenclature,
bacterial polysaccharides, 48:3 13-3 17 52:113-1 I6
of carbohydrates, synthesis of, 31:4 Phosphorus pentachloride
effect on proton nuclear magnetic resonance polycondensation of u-glucose in aqueous,
spectroscopy, 29:23 21:447
of polysaccharides, 29:334 reactions with carbohydrate derivatives,
protection of, 46:202-203 28:239
Phosphoric triamide, hexamethyl- replacement of hydroxyl group by chlorine,
photochemical reaction with carbohydrate 22: I84
esters, 38: 137-142 Phosphorus pentachloride-aluminum chloride,
as solvent rearrangements of saccharides in, 26: 194
in displacement reactions, 24: 14 I Phosphorus pentafluoride, as catalyst in
for sugars, 27: 123 polymerization of 1.6-
for trimethylsilylation, 28:30 anhydrohexopyranoses, 34:74
and thionyl bromide or chloride, reaction Phosphorus pentaoxide
with o-rihonucleosides, 28:250 as catalyst for polycondensation of sugars,
Phosphorochloridic acid 21 :441,452, 454
bis (2,2,2-trichloroethyI) ester, selective oxidation and polymerization of sugars with,
phosphorylation of nucleosides with, 46:6
33:48 Phosphorus sugars
dibenzyl ester biological activity of, 42: 188-190
as phosphorylating agent physical properties of, 42: 19 1
for 2'-deoxynucleosides, 22:345 synthesis and structure of, 42: 135-191
for nucleosides, 22:326 Phosphorus trichloride
for nucleosides, 22:326 as phosphorylating agent for nucleosides,
selective phosphorylation with, 33:48 22:341-342
diphenyl ester, in selective phosphorylation polycondensation of D-glucose in aqueous,
of carbohydrates, 33:4647 21:447
Phosphorochloridites, in nucleotide formation, Phosphorylases, 25:8
36: 159 active sites of, 23:346
Phosphorohydrazidic acid, phenyl ester, as amino acids of, 23:345
phosphorylating agent for nucleosides, and amylo-( I-t6)-glucosidase, mechanism
22:338 ofaction of, 30:312,328,331
Phosphorolysis, of activated nucleosides, function, 51: 141- 142
22:369 in honey, 25:303
Phosphorothioic acid, S-ethyl ester, as kinetics, 23:289, 353
phosphorylating for nucleosides, 22:335 mechanism of action of, 23:356
414 SUBJECT lNDEX
Xylonic acid, D-, salts, preparation of, 29: I 19 5-deoxy-a-~-,23:126, 167, 19&192
Xylononitrile 5-deoxy-o-, 23:122, 126, 128, 148, 160,
tetra-0-acetyl- 192-1 93
D-, ammonolysis of, effect of solvent on, synthesis, 41:9
31:99 tetra-O-acetyl-5-deoxy-o-. mass spectrum
L-, ammonolysis of, effect of solvent on, of, 23:201
31:99 a - D - , 45:74
2,3,4,5-tetra-O-acetyyl-~-,reaction with conformation in solution, 26:85
ammonia, 31:83 crystal structure bibliography, 30:447
Xylo-oligosaccharides, 4 6 5 9 ester of adenosine 5'-pyrophosphate,
chemical shifts, 46:75 enzymic preparation of, 28:343
1,4:3,6-dianhydrohexitols,49: 102-1 09 of uridine 5'-pyrophosphate, enzymic
di-o-fructose dianhydride derivatives, 52:264 preparation of, 28:343
per-0-acetyl derivatives, fructose occurrence of. 28:325
components, 52:265-266 1,2,4-orthobenzoate
dihexulose dianhydrides, 52:248-249 crystal structure bibliography, 30:465,
geminal coupling, 2J ('H,19F), 46:75 34:357
'H-I9F coupling constants, 46:75-77 3-( p-bromobenzoate), crystal structure
long-range coupling bibliography, 30:465
4J, ('H, "F). 46:76-77 reaction with sulhryl chloride, 28:235,
5J, ('H, I9F), 46:76-77 33:76
6J. ('H, 19F),46:77 taste properties. 45:242
per-0-acetyl dihexulose dianhydrides, 5-amino-5-deoxy-, derivative, synthesis,
52:250-25 I 40:97
per-0-acetyl fructose glucose, 52:252 p-D-
preparative liquid chromatography, 46:60 conformation in solution, 26:85
structural-reporter-group concept, 46: 79 taste properties, 45:242
vicinal coupling, 3J (lH,19F), 46:75-76 tetraacetate, conformations of, 24:58
from xylans, 32:347-348,350 5-[(benzyloxycarbonyI)amino]-5-deoxy-a-
Xylopranoside D-, 23:192-193
a-D-, glucopyranosyl-a-o-, preparation of, 5-benzymIdo-5-deoxy-o-, 23: 169
34:265 5-d, P-D-,tetraacetate. preparation of, 27:220
serine-p-o-, and copper(I1) complex, crystal D-
structure bibliography, 34:355 amino-substituted, 47:65
Xylopyranan, carbon-I3 nuclear magnetic derivatives having N-substituents,
resonance spectra, 38:95 equilibria, 47:6465
Xylopyranose 1,3,4-tri-0-acetyl-2-deoxy-2-fluoro-a-
1,2,3,4-tetra-O-benzoyl-p-~-, crystal 'IC-NMR data for, 46:167-168
structure, 43:265-266 'H- and I9F-NMR data for, 46: 104
2,3,4-tri-O-acetyl-a-o-, 43:37 1 5-deoxy-5-phosphino- and-5-phosphinyl-~-,
a-o-Xylopyranose calcium chloride tri hydrate, synthesis of, 42:138-145
crystal structure bibliography, 31:348 3,4-di-O-acetyl-2-bromo-2-deoxy-~-,
Xylopyranose 1,2,3-orthobenzoate. 3 - 0 - ( p - reaction with (p-nitropheny1)-
bromobenzoy1)-a-u-. crystal structure, hydrazine, 25:202, 28:287
43:347-348 1,2:3,4-di-O-isopropylidene-5-thio-a-~-,
Xylopyranoses selective hydrolysis, 39: 17
4-acetamido- a-L-,crystal structure, 43:207-208
4-deoxy-~-,23: 147, 180 N-amino-5-amino-5-deoxy-o-, 23: 1 59
1,2,3-tri- 0-acetyl-o-, 23: 182 0-(a-u-glucopyranosyluronicacid)-( 1+2)-
5-acetamido- 0-p-o-xylopyranosyl-( 1+4)-0-. 24:37 1
526 SUBJECT INDEX
533
534 CONTRIBUTOR INDEX
I L
W
Z
Wallenfels, Kurt, 16:239
Wander, Joseph D., 32: 15 Zahringer, Ulrich, 50:211
Watson, Ronald R., 31:135 Zamojski, Aleksander, 40: 1
Webber, J. M., 15:371, 17:15 Zaranyika, Mark F., 51:243
Weidmann, Hans, 33: I89 Zehavi, Uri, 46: 179
Weigel, Helmut, 18:61,34:1 Zhdanov, Yu. A,, 27:227
Weiss, Alvin H., 29:173 Zilliken, F., 13:237
Weiss, Ekkehard, 17:65 Zorbach, W. Werner, 21:273
This Page Intentionally Left Blank