European J. Biochem.

1 (1967) 375-378

IUPAC-IUB Commission on Biochemical Nomenclature (CBN)

Abbreviated Designation of Amino Acid Derivatives and Pep-tides

Tentative Rules’

These Tentative Rules are an attempt to achieve a broad 1.5 Amino acid symbols denote the L configuration unless
systematization of various types of abbreviated notation otherwise indicated by D or DL appearing before the symbol
already in use [e.g. Brand and Edsall, Ann. Rev. Biochem. 16 and separated from it by a hyphen. When it is desired to
(1947) 224; Report of the Committee on Abbreviations of the make the number of amino acid residues appear in a clearer
American Society of Biological Chemists, December 18, 1959; manner, the hyphen between the configurational prefix and
Report of the Committee on Nomenclature of the European the symbol may be omitted (see 5.3.1.1 et seq.). (Note: The
Peptide Symposium, Pergamon Press, 1963, pp. 261 -269; designation of a n amino acid residue as DL is inappropriate
“Tentative Rules for Abbreviations and Symbols of Chemical for compounds having another amino acid residue with an
Names of Special Interest in Biological Chemistry,” IUPAC asymmetrical center.)
Information Bulletin No. 20, July 1963, pages 16-18; 1965 1.6 Structural formulas of complicated features may be
revision of the latter]. They seek to reconcile the needs of the used along with the abbreviated notation wherever necessary
protein chemist, i.e. indication of amino acid sequences, with for clearity.
those of persons concerned more with the chemical reactions
of proteins and the synthesis of polypeptides, i.e. the need
of conveying more detailed chemical information in abbre- 2. ABBREVIATIONS FOR AMINO ACIDS
viated form.
2.1 Common Amino Acids
1. GENERAL CONSIDERATIONS Alanine Ala Lysine LYS
Arginine Arg Methionine Met
1.1 The symbols chosen are derived from the trivial Asparagine2 Am2 Ornithine Om
names or chemical names of the animo acids and of chemicals Aspartic acid ASP Phenylalanine Phe
reacting with amino acids and polypeptides. For the sake of Proline Pro
Cysteine CYS
clarity, brevity, and listing in tables, the symbols have been, Glutamic acid Glu Serine Ser
wherever possible, restricted to three letters, usually the Glutamine2 Gln2 Threonine T h
first letters of the trivial names. Glycine GlY
1.2 The symbols represent not only the names of the Tryptophan TrP
Histidine His Tyrosine Tyr
compounds but also their structural formulas. Isoleucine Ile Valine Val
1.3 The amino acid symbols by themselves represent the Leucine Leu
amino acids. The use of the symbols t o represent the free
amino acids is not recommended in textual material, but such
use may occasionally be desirable in tables, diagrams, or 2.2 Less Common Amino Acids
figures. Residues of amino acids are represented by addition
of hyphens in specific positions as indicated in Section 3. Abbreviations for less common amino acids should be
1.4 Heteroatoms of amino acid residues ( e . g . OB and Sb’ defined in each publication in which they appear. The follow-
of serine and cysteine, respektively, NSof lysine, N“ of gly- ing principles and notations are recommended.
cine, etc.) do not explicitly appear in the symbol; such 2.2.1 Hydroxyamino Acids.
features are understood to be encompassed by the abbre- Hydroxyl y sine HYl
viation. 3-Hydroxyproline 3HYP
4-Hydroxyproline 4HYP
Document of the IUPAC-IUB Commission on Bio- 2.2.2 allo-Amino Acids.
chemical Nomenclature (CBN), approved by CBN in July allo-Isoleucine aIle
1965 and published by permission of the International Union allo-Hydroxylysine aHyl
of Pure and Applied Chemistry, the International Union of
Biochemistry, and the official publishers t o the International 2.2.3 “Nor” Amino Acids. “Nor” (e.g. in norvaline) is not
Union of Pure and Applied Chemistry, Messrs. Butterworths used in its accepted sense (denoting a lower homologue) but
Scientific Publications. (Published in IUPAC Information t o change the trivial name of a branched chain compound
into that of a straight chain compound (compare with “iso,”
Bulletin No. 25, February 1966, page 32.)
This set of Rules should be regarded as an extension, not paragraph 2.1). “Nor” should therefore be treated as part
a replacement, of Section 2 (Polypeptides and Proteins) of
of the trivial name without special emphasis.
Abbreviations and Symbols for Chemical Names of Special Norvaline Nva
Interest in Biological Chemistry [ J . Biol. Chem. 241 (1966) Norleucine Nle
521; European J . Biochem. 1 (1967) 2591.
Reprints of these Tentative Rules may be obtained from 2.2.4 Higher Unbranched Amino Acids. We suggest the
Waldo E. Cohn, Director, NAS-NRC Office of Biochemical following general rules for guidance in forming abbreviations :
Nomenclature, Oak Ridge National Laboratory, P. 0.Box Y, the functional prefix “amino” should be included in the
Oak Ridge, Tennessee 37831, U.S.A. symbol as the letter “A,” diamino as “D.”
Comments on these Tentative Rules may be sent to any
member of CBN: 0. Hoffmann-Ostenhof (Chairman), W. E. 2Asparagine and glutamine may also be denoted as
Cohn (Secretary), A. E. Braunstein, J. S. Fruton, B. Keil, Asp(NH,) or Asp, and Glu(NH,) or Glu, respectively.
W. Klyne, C. Likbecq, B. G. Malmstrom, R. Schwyzer, E. C.
Slater, or corresponding member, N. Tamiya.
I I
NH2 NH,
26 Europcan J. Biochcm., Vol. 1
376 IUPAC-IUB Tentative Rules :Amino Acid Derivatives and Peptides European J. Biochem.

The trivial name of the parent acid should be abbreviated I I

T r p o r Trp: H,NCHCOOH Arg or Arg: H,NCHCOOH
to leave no more than two or three letters, as convenient and 1 1 I I
necessary for clarity. The word “acid” (“-suure,” etc.) should $HZ (CH,),
be omitted from the symbol as carrying no significant inform- I
ation. Unless otherwise indicated (see paragraph below), P N - NH
I
single groups are in the a position, two amino groups in the
1%
a,w (monocarboxylic acids) or a,a’ positions (dicarboxylic HzN N-
acids). The location of amino acids in positions other than a I I
and w is shown by the appropriate Greek letter prefix. S e r o r Ser: H,NCHCOOH Tyr o r T y r : H,NCHCOOH
1 I I I
Examples :
cc-Aminobutyric acid
a-Aminoadipic acid
a-Aminopimelic acid
a,y-Diaminobutyric acid
Abu
Aad
APm
Dbu
CHZ
0
I

I 0 CH,

0
I
cc,B-Diaminopropionicacid DPr
=,a’-Diaminopimelic acid DPm I
B-Alanine BAla C y s o r Cys: HzNCHCOOH (“half-cystine”)
I I
.s-Aminocaproid acid
B-Aminoadipic acid
~Acp
BAad 7%
-S
2.2.5 Na-Alkyluted Amino Acids. Na-Methylamino acids
are becoming more and more common (e.g. in the large group
of depsipeptides). This justifies special symbols. CYS r--l
Examples : ( C y s t i n e would be: I Cys Cys
CYS
N-Methylglycine (sarcosine) MeGly or Sar
N-Methylisoleucine MeIle
N-Methylvaline, etc. MeVal, etc.
N-Ethyglycine, etc. EtGly, etc.

3. AMINO ACID RESIDUES 3.4 Luck of Hydroxyl on Curboxyl Groups in the Side Chain
3.1 Luck of Hydrogen on the a-Amino Group
The cc-amino group is understood to be at the left-hand dsp or Asp: H,NCHCOOH &lu or Glu: H,NCHCOOH
side of the symbol when using hyphens, and-in special
cases-at the point of the arrow when using arrows to
indicate the direction of the peptide bond (-CO --f NH-,
-NH t CO-).
‘ &HZ
I
b0
I I
CH,
II
CH,
Examples :
I I
co
CH3 I
-Gly: -HNCH,COOH -Ala:
I
-HNCHCOOH
4. SUBSTITUTED AMINO ACIDS
CH3
I 4.1 Substitution in the a-Amino and a-Curboxyl Groups
>Gly or L G l y : >NCH,COOH; > A h o r l A l a : >NCHCOOH This follows logically from 3.1 and 3.2. The following
examples will make the usage clear.
3.2 Luck of Hydroxyl on the cc-Curboxyl Group N-Acetylglycine Ac-Gly
The a-carboxyl group is always understood t o be on the Glycine ethyl ester Gly-OEt
right-hand side of the symbol when using hyphens, and-in Na-Acetyllysine Ac-Lys
such special cases as 5.3.1.3-at the tail of the arrow when Serine methyl ester Ser-OMe
using arrows to indicate the direction of the peptide bond cc-Ethyl-N-acetylglutamate Ac-Glu-OEt
(-CO -+ NH, -NH c CO-). Isoglutamine Glu-NH,
Example: Gly- : H,NCH,CO-. Et
N-Ethyl-N-methylglycine EtMeGly, )Gly,
3.3 Luck of Hydrogen on Amino, Imino, Guunidino, Hydroxyl, Me
and Thiol Functions in the Side Chain
Me
I
Lys o r L y s : H,NCHCOOH I
1 I ~ t - i - ~ i ~
(CH,),
I
NH
I 4.2 Substitution in the Side Chain
I Side chain substituents may be portrayed above or
H i s or His: H,NCHCOOH or H,NCHCOOH below the amino acid symbol, or by placing the symbol for
I I I the substituent in parentheses immediately after the amino
acid symbol.
The use of parentheses should be reserved for a single
symbol denoting a side chain substituent. Where a more
Vol. 1, No. 4, 1967 Commission on Biochemical Nomenclature 377

complex substituent is involved, i t is recommended that the The presence of free, substituted, or ionized functional
vertical stroke and a two-line abbreviation be used. groups can be represented (or stressed) as follows:
OMe H
I
I
Aspartic acid #?-methyl ester Asp or Asp or Asp(0Me) Glycyllysylglycine H-Gly-Lys-Gly -OH
I I t s dihydro- +Hz-Gly-Lys-Gly-OH-2C1-
OMe

Ac
chloride

I t s sodium salt Gly-Lys-Gly-0-

+Q Na+
I
Lys or Lys or Lys(Ac)
NE-Acetyllysine
I Its NE-formyl Gly-Lys-Gly or Gly-Lys(CH0)-Gly
Ac derivative I
CHO
AC
I 5.2 Peptides Substituted at Na
0-Acetylserine Ser or Ser or Ser(Ac)
I Examples :
Ac
Glycylnitroso- GlY
Me glycine " l Y T
I NO
0-Methyltyrosine Tyr or Tyr or Tyr(Me) Glycylsarcosine Gly-Gly or Gly-MeGly
I
Me Me or Gly-Sar
Et
I Ac
A'-Ethylcysteine Cys or Cys or Cys(Et)
Na-Glycyl-Na- Gly--Gly I
kt acetylglycine

5 . POLYPEPTIDES
5.1 Polypeptide Chains
Na-Glycyl-aN-
glycylglycine
"'7
Gly- Gly

Polypeptides may be dealt with in the same manner as

substituted amino acids, e.g.
G1ycylglycine
a-Glutamylglycine
5.3 Cyclic Polypeptides
Gly-Gl y 5.3.1 Homodetic cyclic polypeptides (the ring consists
Glu-Gly of amino acid residues in peptide linkage only). Three
representations are possible:
5.3.1.1 The sequence is formulated in the usual manner

Glu
yGlu
1G- I but placed in parentheses and preceded by (an italic) cyclo.
Example: Gramicidin S =
y-Glutamylglycine or
cyc~o-(-Val-Orn-Leu-D-Phe-Pro-v~l-o~-Leu-D-Phe-Pr~)
I-Gly or (see 1.5, sentence 2)

Glutathione3 Glu or Glu cyclo-(Val-Orn-Leu-DPhe-Pro-Val-Orn-Leu-DPhe-Pro-)

1-Cys-Gly '
I--Cys-Gly
5.3.1.2 The terminal residues may be written in one line,
as in 5.3.1.1, but joined by a lengthened bond. Using the
same example in the two forms (see 1.5):
N"- a-Glutamyllysine
G1uI
LYS

NE-y-Glutamyllysine Glu Lys or Glu Lys or Glu

1-1
5.3.1.3 The residues are written on more than one line,
in which case the CO --f N H direction must be indicated by
arrows, thus (in the optimal manner of 1.5):
Note that Glu would represent the corresponding
+Val + O m -+ Leu + DPhe + Pro-
y s-Gl y L P r o +- DPhe c Leu c O m c V a l e 1
thiolester with a bond between the y-carboxyl of glutamic 5.3.2 Heterodetic cyclic polypeptides (the ring consists
acid and the thiol group of cysteine. of other residues in addition to amino acid residues in peptide
26'
378 IUPAC-IUB Tentative Rules : Amino Acid Derivatives and Peptides European J. Biochem.

linkage) : These follow logically from the formulation of 6.1 N-Protecting Groups of the Urethane Type
substituted amino acids.
Example :
Benzyloxy carbonyl Z-
p-Nitrobenzyloxy carbonyl Z(NO2)-
Oxytocin Cys-Tyr-Ile-Asn-Gln-Cys-Pro-Leu-Gly-NH2 p-Bromobenzyloxycarbonyl Z(Br)-
-! ! p-Methoxybenzyloxycarbonyl Z(0Me)-
p-Methoxyphenylazobenz yloxy carbonyl Mz-
Cyclic ester of threonylglycylglycylglycine p-Phenylazobenzyloxycarbonyl Pz-
tert.-Butyloxycarbonyl Boc-
Cyclopentyloxycarbonyl Poc-
Thr-Gly-Gly-Gly I or H-Thr-Gly-Gly-Gly--
I ! 6.2 Other N-Protecting Groups
6. ABBREVIATIONS FOR SUBSTITUENTS Acetyl Ac-
Benzoyl Bz-
Groups substituted for hydrogen or for hydroxyl may be Tosyl TOS-
indicated either by their structural formulas or by (accepted) Trifluoracetyl Tfa-
abbreviations, e.g. Phthalyl Phtr
Benzvl Bzl-
Benzoylglycine Tritg Trt-
@osly O r c6H5-co-G1Y Or
(hippuric acid) Tetrahydropyranyl ThP
Bz-Gly4 Dinitrophenyl Dnp-
Benzvlthiomethvl Btm-
Glycine methyl Gly-OCH3 o r Gly-OMe o-Ni&ophenylsdfenyl Nps-
ester
6.3 Carboxyl-protectingGroups
Suggestions for the abbreviations of protecting groups
common in polypeptide chemistry follow. All such symbols Methoxy (methyl ester) -0Me
(except those allowed by individual journals, e.g. Bz, Ac, Ph, Ethoxy (ethyl ester) -0Et
Me, Et, etc.) should be defined in each paper. Although Tertiary butoxy (tert-butyl ester) -OBut
symbolization by the use of capital letters throughout would Benzyloxy (benzyl ester) -0Bzl
be useful for distinguishing these symbols from those of the Diphenylmethoxy (benzhydryl ester) -0Bzh
amino acids, we propose the use of one capital letter followed p-Nitrophenoxy (p-nitrophenyl ester) -0Np
by lower-case letters in order not to increase the flood of Phenylthio (phenylthiolester) -SPh
capital-letter abbreviations in biological chemistry. p-Nitrophenylthio -SNp
Cyanomethoxy -0CHZCN
4 Bz- is the symbol generally used for benzoyl in organic
chemistry. Its use for benzyl (which has become rather Note: Contrary to the symbols for amino acid residues,
common in polypeptide chemistry) should be discouraged. the position of the dashes in the symbols for substituents
We propose Bzl- for benzyl. carries no significant information.

These Tentative Rules have been translated into French and German and have appeared
in the Bulletin de la Xoci6t6 de Chimie biologique [49 (1957) I211 and in Hoppe-Xeyler's
Zeitschrift fur physiologische Chemie [348 (1967) 2561.
All tentative Rules of the IUPAC-IUB Commission on Biochemical Nomenclature (CBN),
first published in the Journal of Biological Chemistry [241 (1966) 527,2491 and 29871 and in Bio-
chemistry [6 (1967) 3621 are available from Waldo E. Cohn, Director, NAS-NRC Office of Bio-
chemical Nomenclature, Oak Ridge National Laboratory, P. 0. Box Y, Oak Ridge, Tennessee
37831, U.S.A. :
Abbreviations and Symbols for Chemical Names of Special Interest in Biological Chemistry
[see European J. Biochem. 1 (1967) 2591,
Rules for Naming Synthetic Modifications of NaturaI Peptides [see European J . Biochern. I
(1967) 3791,
Abbreviated Designation of Amino Acid Derivatives and Polypeptides (this document),
Trivial Names of Miscellaneous Compounds of Importance in Biochemistry,
Nomenclature of Quinones with Isoprenoid Side Chains,
Nomenclature and Symbols for Folic Acid and Related Compounds,
Nomenclature of Corrinoids.
A document, OBN-1, describing the (American) NAS-NRC Office of Biochemical Nomen-
clature, and listing other rules affecting biochemical nomenclature is available from its Director,
Dr. Waldo E. Cohn.