Glycine

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9/2/2019 Glycine - Wikipedia

Glycine
Glycine (symbol Gly or G;[4] /ˈɡlaɪsiːn/)[5] is an amino acid that has a
single hydrogen atom as its side chain. It is the simplest amino acid Glycine[1]
(since carbamic acid is unstable), with the chemical formula NH2-CH2-
COOH. Glycine is one of the proteinogenic amino acids. It is encoded by
all the codons starting with GG (GGU, GGC, GGA, GGG). Glycine is
integral to the formation of alpha-helices in secondary protein structure
due to its compact form. For the same reason, it is most abundant amino
acid in collagen triple-helices. Glycine is also an inhibitory
neurotransmitter - interference with its release within the spinal cord
(such as during a Clostridium tetani infection) can cause spastic
paralysis due to uninhibited muscle contraction.
Canonical Zwitterionic form at
Glycine is a colorless, sweet-tasting crystalline solid. It is the only achiral
amino acid physiological pH
proteinogenic amino acid. It can fit into hydrophilic or hydrophobic
form
environments, due to its minimal side chain of only one hydrogen atom.
The acyl radical is glycyl. Names
Preferred IUPAC name
Glycine

Contents Systematic IUPAC name


2-Aminoethanoic acid
History and etymology
Other names
Production
Aminoacetic acid
Chemical reactions Glycocoll
Metabolism
Identifiers
Biosynthesis
Degradation CAS Number 56-40-6 (http://www.c
Physiological function ommonchemistry.or
As a biosynthetic intermediate g/ChemicalDetail.asp
As a neurotransmitter x?ref=56-40-6) 
Uses 3D model Interactive image (htt
Animal and human foods (JSmol)
Chemical feedstock
ps://chemapps.stolaf.
Laboratory research edu/jmol/jmol.php?m
odel=C%28C%28%3
Presence in space
DO%29O%29N)
Presence in foods
Zwitterion: Interactive
See also
image (https://chema
References
pps.stolaf.edu/jmol/j
Further reading
mol.php?model=C%
External links 28C%28%3DO%2
9%5BO-%5D%29%5
BNH3%2B%5D)
History and etymology
Abbreviations Gly, G
ChEBI CHEBI:15428 (http
s://www.ebi.ac.uk/ch
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Glycine was discovered in 1820 by the French chemist Henri Braconnot ebi/searchId.do?che
when he hydrolyzed gelatin by boiling it with sulfuric acid.[6] He biId=15428) 
originally called it "sugar of gelatin",[7][8] but the French chemist Jean-
ChEMBL ChEMBL773 (https://
Baptiste Boussingault showed that it contained nitrogen.[9] The
www.ebi.ac.uk/chem
American scientist Eben Norton Horsford, then a student of the German
bldb/index.php/comp
chemist Justus von Liebig, proposed the name "glycocoll";[10][11]
ound/inspect/ChEMB
however, the Swedish chemist Berzelius suggested the simpler name
L773) 
"glycine".[12][13] The name comes from the Greek word γλυκύς "sweet
tasting"[14] (which is also related to the prefixes glyco- and gluco-, as in ChemSpider 730 (http://www.che
glycoprotein and glucose). In 1858, the French chemist Auguste mspider.com/Chemic
Cahours determined that glycine was an amine of acetic acid.[15] al-Structure.730.htm
l) 

Production DrugBank DB00145 (https://ww


w.drugbank.ca/drugs/
Although glycine can be isolated from hydrolyzed protein, this is not
DB00145) 
used for industrial production, as it can be manufactured more
conveniently by chemical synthesis.[16] The two main processes are ECHA InfoCard 100.000.248 (https://
amination of chloroacetic acid with ammonia, giving glycine and echa.europa.eu/subs
ammonium chloride,[17] and the Strecker amino acid synthesis,[18] tance-information/-/s
which is the main synthetic method in the United States and Japan.[19] ubstanceinfo/100.00
About 15 thousand tonnes are produced annually in this way.[20] 0.248)
EC Number 200-272-2
Glycine is also cogenerated as an impurity in the synthesis of EDTA,
IUPHAR/BPS 727 (http://www.guid
arising from reactions of the ammonia coproduct.[21]
etopharmacology.or
g/GRAC/LigandDispl
Chemical reactions ayForward?tab=sum
Its acid-base properties are most important. In aqueous solution, glycine mary&ligandId=727)
itself is amphoteric: at low pH the molecule can be protonated with a KEGG D00011 (https://www.
pKa of about 2.4 and at high pH it loses a proton with a pKa of about 9.6 kegg.jp/entry/D0001
(precise values of pKa depend on temperature and ionic strength). 1) 
PubChem CID 750 (https://pubche
m.ncbi.nlm.nih.gov/c
ompound/750)
UNII TE7660XO1C (http
s://fdasis.nlm.nih.go
v/srs/srsdirect.jsp?re
gno=TE7660XO1C) 

CompTox DTXSID9020667 (htt


Dashboard
ps://comptox.epa.go
(EPA)
v/dashboard/DTXSID
9020667)

InChI
SMILES
Properties
Chemical C2H5NO2
formula
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Molar mass 75.067 g·mol−1


Appearance White solid
Density 1.607 g/cm3
Melting point 233 °C (451 °F;
506 K)
(decomposition)
Solubility in 24.99 g/100 mL (25
water °C)[2]
Solubility soluble in pyridine
sparingly soluble in
ethanol
insoluble in ether
Acidity (pKa) 2.34 (carboxyl), 9.6
(amino)[3]
Magnetic -40.3·10−6 cm3/mol
susceptibility (χ)
Pharmacology
ATC code B05CX03 (WHO (htt
ps://www.whocc.no/a
tc_ddd_index/?code
=B05CX03))
Hazards
Safety data See: data page
sheet
Lethal dose or concentration (LD, LC):
LD50 (median 2600 mg/kg (mouse,
dose) oral)
Supplementary data page
Structure and Refractive index (n),
properties Dielectric constant
(εr), etc.
Thermodynamic Phase behaviour
data solid–liquid–gas
Spectral data UV, IR, NMR, MS
Except where otherwise noted, data
are given for materials in their standard
state (at 25 °C [77 °F], 100 kPa).
 verify (what is   ?)
Infobox references

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Glycine is a white crystalline solid

Glycine functions as a bidentate ligand for many metal ions. A typical complex is Cu(glycinate)2, i.e.
Cu(H2NCH2CO2)2, which exists both in cis and trans isomers.

As a bifunctional molecule, glycine reacts with many reagents. These can be classified into N-centered and carboxylate-
center reactions.

The amine undergoes the expected reactions. With acid chlorides, one obtains the amidocarboxylic acid, such as
hippuric acid[22] and acetylglycine.[23]With nitrous acid, one obtains glycolic acid (van Slyke determination). With
methyl iodide, the amine becomes quaternized to give betaine, a natural product:

H3N+CH2CO2- 3 CH3I → (CH3)3N+CH2CO2- + 3 HI

Glycine condenses with itself to give peptides, beginning with the formation of glycylglycine:

2 H3N+CH2CO2- → H3N+CH2C(O)NHCH2CO2- + H2O

Pyrolysis of glycine or glycylglycine gives 2,5-diketopiperazine, the cyclic diamide.

Metabolism

Biosynthesis
Glycine is not essential to the human diet, as it is biosynthesized in the body from the amino acid serine, which is in
turn derived from 3-phosphoglycerate, but the metabolic capacity for glycine biosynthesis does not satisfy the need for
collagen synthesis.[24] In most organisms, the enzyme serine hydroxymethyltransferase catalyses this transformation
via the cofactor pyridoxal phosphate:[25]

serine + tetrahydrofolate → glycine + N5,N10-Methylene tetrahydrofolate + H2O

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In the liver of vertebrates, glycine synthesis is catalyzed by glycine synthase (also called glycine cleavage enzyme). This
conversion is readily reversible:[25]

+
CO2 + NH4 + N5,N10-Methylene tetrahydrofolate + NADH + H+ ⇌ Glycine + tetrahydrofolate
+ NAD+

Degradation
Glycine is degraded via three pathways. The predominant pathway in animals and plants is the reverse of the glycine
synthase pathway mentioned above. In this context, the enzyme system involved is usually called the glycine cleavage
system:[25]

Glycine + tetrahydrofolate + NAD+ ⇌ CO 2


+
+ NH4 + N5,N10-Methylene tetrahydrofolate +
NADH + H+

In the second pathway, glycine is degraded in two steps. The first step is the reverse of glycine biosynthesis from serine
with serine hydroxymethyl transferase. Serine is then converted to pyruvate by serine dehydratase.[25]

In the third pathway of its degradation, glycine is converted to glyoxylate by D-amino acid oxidase. Glyoxylate is then
oxidized by hepatic lactate dehydrogenase to oxalate in an NAD+-dependent reaction.[25]

The half-life of glycine and its elimination from the body varies significantly based on dose.[26] In one study, the half-
life varied between 0.5 and 4.0 hours.[26]

Physiological function
The principal function of glycine is as a precursor to proteins. Most proteins incorporate only small quantities of
glycine, a notable exception being collagen, which contains about 35% glycine due to its periodically repeated role in
the formation of collagen's helix structure in conjunction with hydroxyproline.[25][27] In the genetic code, glycine is
coded by all codons starting with GG, namely GGU, GGC, GGA and GGG.

As a biosynthetic intermediate
In higher eukaryotes, δ-aminolevulinic acid, the key precursor to porphyrins, is biosynthesized from glycine and
succinyl-CoA by the enzyme ALA synthase. Glycine provides the central C2N subunit of all purines.[25]

As a neurotransmitter
Glycine is an inhibitory neurotransmitter in the central nervous system, especially in the spinal cord, brainstem, and
retina. When glycine receptors are activated, chloride enters the neuron via ionotropic receptors, causing an Inhibitory
postsynaptic potential (IPSP). Strychnine is a strong antagonist at ionotropic glycine receptors, whereas bicuculline is a
weak one. Glycine is a required co-agonist along with glutamate for NMDA receptors. In contrast to the inhibitory role
of glycine in the spinal cord, this behaviour is facilitated at the (NMDA) glutamatergic receptors which are
excitatory.[28] The LD50 of glycine is 7930 mg/kg in rats (oral),[29] and it usually causes death by hyperexcitability.

Uses
In the US, glycine is typically sold in two grades: United States Pharmacopeia (“USP”), and technical grade. USP grade
sales account for approximately 80 to 85 percent of the U.S. market for glycine. If purity greater than the USP standard
is needed, for example for intravenous injections, a more expensive pharmaceutical grade glycine can be used.

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Technical grade glycine, which may or may not meet USP grade standards, is sold at a lower price for use in industrial
applications, e.g., as an agent in metal complexing and finishing.[30]

Animal and human foods


Glycine is not widely used in foods for its nutrional value, except in
infusions. Instead glycine's role in food chemistry is as a flavorant. It is
mildly sweet, and it counters the aftertaste of saccharine. It also has
preservative properties, perhaps owing to its complexation to metal ions.
Metal glycinate complexes, e.g. copper(II) glycinate are used as
supplements for animal feeds.[20]

Structure of cis-
Chemical feedstock Cu(glycinate)2(H2O).[31]
Glycine is an intermediate in the synthesis of a variety of chemical
products. It is used in the manufacture of the herbicides glyphosate,[32]
iprodione, glyphosine, imiprothrin, and eglinazine.[20] It is used as an intermediate of the medicine such as
thiamphenicol.

Laboratory research
Glycine is a significant component of some solutions used in the SDS-PAGE method of protein analysis. It serves as a
buffering agent, maintaining pH and preventing sample damage during electrophoresis. Glycine is also used to remove
protein-labeling antibodies from Western blot membranes to enable the probing of numerous proteins of interest from
SDS-PAGE gel. This allows more data to be drawn from the same specimen, increasing the reliability of the data,
reducing the amount of sample processing, and number of samples required. This process is known as stripping.

Presence in space
The presence of glycine outside the earth was confirmed in 2009, based on the analysis of samples that had been taken
in 2004 by the NASA spacecraft Stardust from comet Wild 2 and subsequently returned to earth. Glycine had
previously been identified in the Murchison meteorite in 1970.[33] The discovery of cometary glycine bolstered the
theory of panspermia, which claims that the "building blocks" of life are widespread throughout the Universe.[34] In
2016, detection of glycine within Comet 67P/Churyumov-Gerasimenko by the Rosetta spacecraft was announced.[35]

The detection of glycine outside the solar system in the interstellar medium has been debated.[36] In 2008, the Max
Planck Institute for Radio Astronomy discovered the spectral lines of a glycine-like molecule aminoacetonitrile in the
Large Molecule Heimat, a giant gas cloud near the galactic center in the constellation Sagittarius.[37]

Presence in foods
Food sources of glycine[38]
Food g/100g
Snacks, pork skins 11.04
Sesame seeds flour (low fat) 3.43
Beverages, Protein powder soy based 2.37
Seeds, safflower seed meal, partially defatted 2.22
Meat, bison, beef and others (various parts) 1.5-2.0
Gelatin desserts 1.96
Seeds, pumpkin and squash seed kernels 1.82
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Turkey, all classes, back, meat and skin 1.79


Chicken, broilers or fryers, meat and skin 1.74
Pork, ground, 96% lean / 4% fat, cooked, crumbles 1.71
Bacon and beef sticks 1.64
Peanuts 1.63
Crustaceans, spiny lobster 1.59
Spices, mustard seed, ground 1.59
Salami 1.55
Nuts, butternuts, dried 1.51
Fish, salmon, pink, canned, drained solids 1.42
Almonds 1.42
Fish, mackerel 0.93
Cereals ready-to-eat, granola, homemade 0.81
Leeks, (bulb and lower-leaf portion), freeze-dried 0.7
Cheese, parmesan (and others), grated 0.56
Soybeans, green, cooked, boiled, drained, without salt 0.51
Bread, protein (includes gluten) 0.47
Egg, whole, cooked, fried 0.47
Beans, white, mature seeds, cooked, boiled, with salt 0.38
Lentils, mature seeds, cooked, boiled, with salt 0.37

See also
Trimethylglycine
Amino acid neurotransmitter

References
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ISBN 091191028X, 4386.
2. "Solubilities and densities" (http://prowl.rockefeller.edu/aainfo/solub.htm). Prowl.rockefeller.edu. Retrieved
2013-11-13.
3. Dawson, R.M.C., et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.
4. "Nomenclature and Symbolism for Amino Acids and Peptides" (http://www.chem.qmul.ac.uk/iupac/AminoAcid/AA1
n2.html). IUPAC-IUB Joint Commission on Biochemical Nomenclature. 1983. Archived (https://web.archive.org/we
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5. "Glycine | Definition of glycine in English by Oxford Dictionaries" (https://en.oxforddictionaries.com/definition/glycin
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6. R.H.A. Plimmer (1912) [1908]. R.H.A. Plimmer; F.G. Hopkins (eds.). The chemical composition of the proteins (htt
ps://books.google.com/?id=7JM8AAAAIAAJ&pg=PA112). Monographs on biochemistry. Part I. Analysis (2nd ed.).
London: Longmans, Green and Co. p. 82. Retrieved January 18, 2010.
7. Braconnot, Henri (1820). "Sur la conversion des matières animales en nouvelles substances par le moyen de
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animal materials into new substances by means of sulfuric acid]. Annales de Chimie et de Physique. 2nd series (in
French). 13: 113–125. ; see p. 114.
8. MacKenzie, Colin (1822). One Thousand Experiments in Chemistry: With Illustrations of Natural Phenomena; and
Practical Observations on the Manufacturing and Chemical Processes at Present Pursued in the Successful
Cultivation of the Useful Arts … (https://books.google.com/books?id=1So5AAAAMAAJ&pg=PA557). Sir R. Phillips
and Company.

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9. Boussingault (1838). "Sur la composition du sucre de gélatine et de l'acide nitro-saccharique de Braconnot" (http
s://babel.hathitrust.org/cgi/pt?id=mdp.39015035450702;view=1up;seq=515) [On the composition of sugar of
gelatine and of nitro-glucaric acid of Braconnot]. Comptes Rendus (in French). 7: 493–495.
10. Horsford, E.N. (1847). "Glycocoll (gelatine sugar) and some of its products of decomposition" (https://babel.hathitr
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AJ&pg=PA167). Courier Corporation. ISBN 9780486642352.
12. Berzelius, Jacob (1848). Jahres-Bericht über die Fortschritte der Chemie und Mineralogie (Annual Report on the
Progress of Chemistry and Mineralogy) (https://books.google.com/books?id=mDc4AQAAIAAJ&dq=%22glycin%22
&pg=PA654#v=onepage&q=%22glycin%22&f=false). vol. 47. Tübigen, (Germany): Laupp. p. 654. From p. 654:
"Er hat dem Leimzucker als Basis den Namen Glycocoll gegeben. … Glycin genannt werden, und diesen Namen
werde ich anwenden." (He [i.e., the American scientist Eben Norton Horsford, then a student of the German
chemist Justus von Liebig] gave the name "glycocoll" to Leimzucker [sugar of gelatine], a base. This name is not
euphonious and has besides the flaw that it clashes with the names of the rest of the bases. It is compounded
from γλυχυς (sweet) and χολλα (animal glue). Since this organic base is the only [one] which tastes sweet, then it
can much more briefly be named "glycine", and I will use this name.)
13. Nye, Mary Jo (1999). Before Big Science: The Pursuit of Modern Chemistry and Physics, 1800-1940 (https://book
s.google.com/books?id=qKjxtZvnBKQC&pg=PA141). Harvard University Press. ISBN 9780674063822.
14. "glycine" (http://oxforddictionaries.com/definition/american_english/glycine). Oxford Dictionaries. Retrieved
2015-12-06.
15. Cahours, A. (1858). "Recherches sur les acides amidés" (https://babel.hathitrust.org/cgi/pt?id=umn.31951d00008
355e;view=1up;seq=1050) [Investigations into aminated acids]. Comptes Rendus (in French). 46: 1044–1047.
16. Okafor, Nduka (2016-03-09). Modern Industrial Microbiology and Biotechnology (https://books.google.com/books?i
d=PTm1CwAAQBAJ&pg=PA385). CRC Press. ISBN 9781439843239.
17. Ingersoll, A. W.; Babcock, S. H. (1932). "Hippuric acid" (http://www.orgsyn.org/demo.aspx?prep=cv2p0328).
Organic Syntheses. 12: 40.; Collective Volume, 2, p. 328
18. Wiley (2007-12-14). Kirk-Othmer Food and Feed Technology, 2 Volume Set (https://books.google.com/books?id=f-
-1V1ftgtsC&pg=PA38). John Wiley & Sons. ISBN 9780470174487.
19. "Glycine Conference (prelim)" (https://web.archive.org/web/20120222063555/http://www.usitc.gov/trade_remedy/7
31_ad_701_cvd/investigations/2007/glycine_from_india_japan_korea/preliminary/DOC/Glycine%20Conference%2
0%28prelim%29.wpd). USITC. Archived from the original on 2012-02-22. Retrieved 2014-06-13.
20. Drauz, Karlheinz; Grayson, Ian; Kleemann, Axel; Krimmer, Hans-Peter; Leuchtenberger, Wolfgang and
Weckbecker, Christoph (2007). "Amino Acids". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-
VCH.
21. Hart, J. Roger (2005). "Ethylenediaminetetraacetic Acid and Related Chelating Agents". Ullmann's Encyclopedia
of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_095 (https://doi.org/10.1002%2F14356
007.a10_095).
22. Ingersoll, A. W.; Babcock, S. H. (1932). "Hippuric Acid". Org. Synth. 12: 40. doi:10.15227/orgsyn.012.0040 (https://
doi.org/10.15227%2Forgsyn.012.0040).
23. Herbst, R. M.; Shemin, D. (1939). "Acetylglycine". Org. Synth. 19: 4. doi:10.15227/orgsyn.019.0004 (https://doi.or
g/10.15227%2Forgsyn.019.0004).
24. Meléndez-Hevia, E; De Paz-Lugo, P; Cornish-Bowden, A; Cárdenas, M. L. (December 2009). "A weak link in
metabolism: the metabolic capacity for glycine biosynthesis does not satisfy the need for collagen synthesis".
Journal of Biosciences. 34 (6): 853–72. doi:10.1007/s12038-009-0100-9 (https://doi.org/10.1007%2Fs12038-009-
0100-9). PMID 20093739 (https://www.ncbi.nlm.nih.gov/pubmed/20093739).
25. Nelson, David L.; Cox, Michael M. (2005), Principles of Biochemistry (4th ed.), New York: W. H. Freeman, pp. 127,
675–77, 844, 854, ISBN 0-7167-4339-6
26. Hahn RG (1993). "Dose-dependent half-life of glycine". Urological Research. 21 (4): 289–291.
doi:10.1007/BF00307714 (https://doi.org/10.1007%2FBF00307714). PMID 8212419 (https://www.ncbi.nlm.nih.go
v/pubmed/8212419).

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27. Szpak, Paul (2011). "Fish bone chemistry and ultrastructure: implications for taphonomy and stable isotope
analysis" (https://uwo.academia.edu/PaulSzpak/Papers/827788/Fish_Bone_Chemistry_and_Ultrastructure_Implic
ations_for_Taphonomy_and_Stable_Isotope_Analysis). Journal of Archaeological Science. 38 (12): 3358–3372.
doi:10.1016/j.jas.2011.07.022 (https://doi.org/10.1016%2Fj.jas.2011.07.022).
28. "Recent development in NMDA receptors" (http://www.cmj.org/Periodical/paperlist.asp?id=LW7347&linkintype=pu
bmed). Chinese Medical Journal. 2000.
29. "Safety (MSDS) data for glycine" (http://physchem.ox.ac.uk/MSDS/GL/glycine.html). The Physical and Theoretical
Chemistry Laboratory Oxford University. 2005. Retrieved 2006-11-01.
30. "Glycine From Japan and Korea" (http://www.usitc.gov/publications/701_731/pub3980.pdf) (PDF). U.S.
International Trade Commission. January 2008. Retrieved 2014-06-13.
31. Casari, B. M.; Mahmoudkhani, A. H.; Langer, V. (2004). "A Redetermination of cis-Aquabis(glycinato-
κ2N,O)copper(II)". Acta Cryst. E. 60: m1949-m1951. doi:10.1107/S1600536804030041 (https://doi.org/10.1107%2
FS1600536804030041).
32. Stahl, Shannon S.; Alsters, Paul L. (2016-07-13). Liquid Phase Aerobic Oxidation Catalysis: Industrial Applications
and Academic Perspectives (https://books.google.com/books?id=z5-tDAAAQBAJ&pg=PA268). John Wiley &
Sons. ISBN 9783527690152.
33. Kvenvolden, Keith A.; Lawless, James; Pering, Katherine; Peterson, Etta; Flores, Jose; Ponnamperuma, Cyril;
Kaplan, Isaac R.; Moore, Carleton (1970). "Evidence for extraterrestrial amino-acids and hydrocarbons in the
Murchison meteorite". Nature. 228 (5275): 923–926. Bibcode:1970Natur.228..923K (http://adsabs.harvard.edu/ab
s/1970Natur.228..923K). doi:10.1038/228923a0 (https://doi.org/10.1038%2F228923a0). PMID 5482102 (https://w
ww.ncbi.nlm.nih.gov/pubmed/5482102).
34. Reuters (18 August 2009). "Building block of life found on comet - Thomson Reuters 2009" (https://www.reuters.co
m/article/scienceNews/idUSTRE57H02I20090818). Retrieved 2009-08-18.
35. European Space Agency (27 May 2016). "Rosetta's comet contains ingredients for life" (http://sci.esa.int/rosetta/5
7858-rosettas-comet-contains-ingredients-for-life/). Retrieved 2016-06-05.
36. Snyder LE, Lovas FJ, Hollis JM, et al. (2005). "A rigorous attempt to verify interstellar glycine". Astrophys J. 619
(2): 914–930. arXiv:astro-ph/0410335 (https://arxiv.org/abs/astro-ph/0410335). Bibcode:2005ApJ...619..914S (htt
p://adsabs.harvard.edu/abs/2005ApJ...619..914S). doi:10.1086/426677 (https://doi.org/10.1086%2F426677).
37. Staff. "Organic Molecule, Amino Acid-Like, Found In Constellation Sagittarius 27 March 2008 - Science Daily" (htt
ps://www.sciencedaily.com/releases/2008/03/080326161658.htm). Retrieved 2008-09-16.
38. "National Nutrient Database for Standard Reference" (https://web.archive.org/web/20150303000000/http://www.na
l.usda.gov/fnic/foodcomp/search/). U.S. Department of Agriculture. Archived from the original (http://www.nal.usda.
gov/fnic/foodcomp/search/) on 2015-03-03. Retrieved 2009-09-07.

Further reading
Kuan YJ, Charnley SB, Huang HC, et al. (2003). "Interstellar glycine". Astrophys J. 593 (2): 848–867.
Bibcode:2003ApJ...593..848K (http://adsabs.harvard.edu/abs/2003ApJ...593..848K). doi:10.1086/375637 (https://
doi.org/10.1086%2F375637).
Rachel Nowak. "Amino acid found in deep space - 18 July 2002 - New Scientist" (https://www.newscientist.com/ne
ws/news.jsp?id=ns99992558). Retrieved 2007-07-01.

External links
Glycine MS Spectrum (http://gmd.mpimp-golm.mpg.de/Spectrums/8a79d6c1-4849-4634-afe1-112d6e346bfb.asp
x)
Glycine (http://www.pdrhealth.com/drugs/altmed/altmed-mono.aspx?contentFileName=ame0084.xml&contentNam
e=Glycine&contentId=247) at PDRHealth.com
Glycine cleavage system (http://www.chem.qmul.ac.uk/iubmb/enzyme/reaction/AminoAcid/GlyCleave.html)
Glycine Therapy - A New Direction for Schizophrenia Treatment? (http://www.schizophrenia.com/glycinetreat.htm)
"Organic Molecule, Amino Acid-Like, Found In Constellation Sagittarius" (https://www.sciencedaily.com/releases/2
008/03/080326161658.htm). ScienceDaily. 27 March 2008.
Guochuan E. Tsai (1 December 2008). "A New Class of Antipsychotic Drugs: Enhancing Neurotransmission
Mediated by NMDA Receptors" (http://www.psychiatrictimes.com/display/article/10168/1357569). Psychiatric
Times. 25 (14).
https://en.wikipedia.org/wiki/Glycine 9/10
9/2/2019 Glycine - Wikipedia

ChemSub Online (Glycine) (http://chemsub.online.fr/name/glycine.html).


NASA scientists have discovered glycine, a fundamental building block of life, in samples of comet Wild 2 returned
by NASA's Stardust spacecraft. (http://www.jpl.nasa.gov/news/news.cfm?release=2009-126)

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