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词条 Glycine
释义

  1. History and etymology

  2. Production

  3. Acid-base properties

  4. Metabolism

     Biosynthesis  Degradation 

  5. Physiological function

     As a biosynthetic intermediate  As a neurotransmitter 

  6. Uses

     Animal and human foods  Cosmetics and miscellaneous applications  Chemical feedstock  Laboratory research    Industrial Use  

  7. Presence in space

  8. Presence in foods

  9. See also

  10. References

  11. Further reading

  12. External links

{{other uses}}{{redirect|Gly|the unit of measurement|light-year}}{{chembox
| Watchedfields = changed
| verifiedrevid = 464190930
| Reference =[1]
| ImageFileR1 = Glycine-zwitterion-2D-skeletal.png
| ImageSizeR1 = 120px
| ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageFileL1 = Glycin - Glycine.svg
| ImageSizeL1 = 73px
| ImageFileR2 = Glycine-from-xtal-2008-3D-balls.png
| ImageSizeR2 = 120px
| ImageNameR2 = Zwitterion of glycine
| ImageFileL2 = Glycine-3D-balls.png
| ImageSizeL2 = 100px
| ImageCaptionL2 = Canonical amino acid form
| ImageCaptionR2 = Zwitterionic form at physiological pH
| PIN = Glycine
| SystematicName =2-Aminoethanoic acid
| OtherNames = Aminoacetic acid
Glycocoll
|Section1={{Chembox Identifiers
| Abbreviations = Gly, G
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = TE7660XO1C
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 773
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00011
| InChI = 1/C2H5NO2/c3-1-2(4)5/h1,3H2,(H,4,5)
| InChIKey = DHMQDGOQFOQNFH-UHFFFAOYAW
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C2H5NO2/c3-1-2(4)5/h1,3H2,(H,4,5)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = DHMQDGOQFOQNFH-UHFFFAOYSA-N
| CASNo = 56-40-6
| CASNo_Ref = {{cascite|correct|CAS}}
| EC_number = 200-272-2
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 730
| PubChem = 750
| IUPHAR_ligand = 727
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00145
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 15428
| SMILES = C(C(=O)O)N
| SMILES1 = C(C(=O)[O-])[NH3+]
| SMILES1_Comment = Zwitterion
}}
|Section2={{Chembox Properties
| C=2 | H=5 | N=1 | O=2
| Appearance = White solid
| Density = 1.607 g/cm3
| MeltingPtC = 233
| MeltingPt_notes = (decomposition)
| Solubility = 24.99 g/100 mL (25 °C)[2]
| SolubleOther = soluble in pyridine
sparingly soluble in ethanol
insoluble in ether
| pKa = 2.34 (carboxyl), 9.6 (amino)[3]
| MagSus = -40.3·10−6 cm3/mol
|Section6={{Chembox Pharmacology
| ATCCode_prefix = B05
| ATCCode_suffix = CX03
}}
|Section7={{Chembox Hazards
| FlashPt =
| AutoignitionPt =
| LD50 = 2600 mg/kg (mouse, oral)
}}

Glycine (symbol Gly or G;[4] {{IPAc-en|ˈ|ɡ|l|aɪ|s|iː|n}})[5] is an amino acid that has a single hydrogen atom as its side chain. It is the simplest amino acid, 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 also known as a "helix breaker", due to its ability to act as a hinge in the secondary structure of proteins.

Glycine is a colorless, sweet-tasting crystalline solid. It is the only achiral proteinogenic amino acid. It can fit into hydrophilic or hydrophobic environments, due to its minimal side chain of only one hydrogen atom. The acyl radical is glycyl.

History and etymology

Glycine was discovered in 1820 by the French chemist Henri Braconnot when he hydrolyzed gelatin by boiling it with sulfuric acid.[6] He originally called it "sugar of gelatin",[7][8] but the French chemist Jean-Baptiste Boussingault showed that it contained nitrogen.[9] The American scientist Eben Norton Horsford, then a student of the German chemist Justus von Liebig, proposed the name "glycocoll";[10][11] however, the Swedish chemist Berzelius suggested the simpler name "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 glycoprotein and glucose). In 1858, the French chemist Auguste Cahours determined that glycine was an amine of acetic acid.[15]

Production

Although glycine can be isolated from hydrolyzed protein, this is not used for industrial production, as it can be manufactured more conveniently by chemical synthesis.[16] The two main processes are amination of chloroacetic acid with ammonia, giving glycine and ammonium chloride,[17] and the Strecker amino acid synthesis,[18] which is the main synthetic method in the United States and Japan.[19] About 15 thousand tonnes are produced annually in this way.[20]

Glycine is also cogenerated as an impurity in the synthesis of EDTA, arising from reactions of the ammonia coproduct.[21]

Acid-base properties

In aqueous solution, glycine itself is amphoteric: at low pH the molecule can be protonated with a pKa of about 2.4 and at high pH it loses a proton with a pKa of about 9.6 (precise values of pKa depend on temperature and ionic strength).

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.[22] In most organisms, the enzyme serine hydroxymethyltransferase catalyses this transformation via the cofactor pyridoxal phosphate:[23]

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

In the liver of vertebrates, glycine synthesis is catalyzed by glycine synthase (also called glycine cleavage enzyme). This conversion is readily reversible:[23]

CO2 + NH{{su|b=4|p=+}} + 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:[23]

Glycine + tetrahydrofolate + NAD+ ⇌ CO2 + NH{{su|b=4|p=+}} + 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.[23]

In the third pathway of glycine 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.[23]

The half-life of glycine and its elimination from the body varies significantly based on dose.[28] In one study, the half-life varied between 0.5 and 4.0 hours.[23]

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.[24][25] 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.[24]

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.[26] The {{LD50}} of glycine is 7930 mg/kg in rats (oral),[27] 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. 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.[28]

Animal and human foods

USP glycine has a wide variety of uses, including as an additive in pet food and animal feed, in foods and pharmaceuticals as a sweetener/taste enhancer, or as a component of food supplements and protein drinks.

Two glycine molecules in a dipeptide form are referred to as a diglycinate. Because they use a different set of transporters in the gut, dipeptides can be use to enhance mineral absorption.[29]

Cosmetics and miscellaneous applications

Glycine serves as a buffering agent in antacids, analgesics, antiperspirants, cosmetics, and toiletries.

A variety of industrial and chemical processes use glycine or its derivatives, such as the production of fertilizers and metal complexing agents.[30]

Chemical feedstock

Glycine is an intermediate in the synthesis of a variety of chemical products. It is used in the manufacture of the herbicide glyphosate.[31]

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.

Industrial Use

It is widely used as an intermediate of the medicine such as thiamphenicol, as an intermediate in the production of glyphosate, as a solvent for removing carbon dioxide (CO2) in the fertilizer industry, and as the galvanizing solution in electroplating.[32][33]

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.[34] The discovery of cometary glycine bolstered the theory of panspermia, which claims that the "building blocks" of life are widespread throughout the Universe.[35] In 2016, detection of glycine within Comet 67P/Churyumov-Gerasimenko by the Rosetta spacecraft was announced.[36]

The detection of glycine outside the solar system in the interstellar medium has been debated.[37] 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.[38]

Presence in foods

Food sources of glycine[39]
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
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

1. ^{{Merck11th|4386}}.
2. ^{{cite web|url=http://prowl.rockefeller.edu/aainfo/solub.htm |title=Solubilities and densities |publisher=Prowl.rockefeller.edu |date= |accessdate=2013-11-13}}
3. ^Dawson, R.M.C., et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.
4. ^{{cite web| url = http://www.chem.qmul.ac.uk/iupac/AminoAcid/AA1n2.html | title = Nomenclature and Symbolism for Amino Acids and Peptides | publisher = IUPAC-IUB Joint Commission on Biochemical Nomenclature | year = 1983 | accessdate = 5 March 2018| archiveurl= https://web.archive.org/web/20081009023202/http://www.chem.qmul.ac.uk/iupac/AminoAcid/AA1n2.html| archivedate= 9 October 2008 | deadurl= no}}
5. ^{{Cite web | url=https://en.oxforddictionaries.com/definition/glycine | title=Glycine | Definition of glycine in English by Oxford Dictionaries}}
6. ^{{cite book |author= R.H.A. Plimmer |editor1=R.H.A. Plimmer |editor2=F.G. Hopkins |title= The chemical composition of the proteins |url= https://books.google.com/?id=7JM8AAAAIAAJ&pg=PA112 |accessdate= January 18, 2010 |edition= 2nd |series= Monographs on biochemistry |volume= Part I. Analysis |origyear= 1908 |year= 1912 |publisher= Longmans, Green and Co. |location= London|page= 82}}
7. ^{{cite journal|last1=Braconnot|first1=Henri|title=Sur la conversion des matières animales en nouvelles substances par le moyen de l'acide sulfurique|journal=Annales de Chimie et de Physique|date=1820|volume=13|pages=113–125|url=https://babel.hathitrust.org/cgi/pt?id=hvd.hx3dvk;view=1up;seq=119|series=2nd series|trans-title=On the conversion of animal materials into new substances by means of sulfuric acid|language=French}} ; see p. 114.
8. ^{{Cite book|url=https://books.google.com/books?id=1So5AAAAMAAJ&pg=PA557|title=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 … |last=MacKenzie|first=Colin|date=1822|publisher=Sir R. Phillips and Company|language=en}}
9. ^{{cite journal|last1=Boussingault|title=Sur la composition du sucre de gélatine et de l'acide nitro-saccharique de Braconnot|journal=Comptes Rendus|date=1838|volume=7|pages=493–495|url=https://babel.hathitrust.org/cgi/pt?id=mdp.39015035450702;view=1up;seq=515|trans-title=On the composition of sugar of gelatine and of nitro-glucaric acid of Braconnot|language=French}}
10. ^{{cite journal|last1=Horsford|first1=E.N.|title=Glycocoll (gelatine sugar) and some of its products of decomposition|journal=The American Journal of Science and Arts|date=1847|volume=3|pages=369–381|url=https://babel.hathitrust.org/cgi/pt?id=hvd.32044102902764;view=1up;seq=381|series=2nd series}}
11. ^{{Cite book|url=https://books.google.com/books?id=89BIAwAAQBAJ&pg=PA167|title=The Development of Modern Chemistry|last=Ihde|first=Aaron J.|date=1970|publisher=Courier Corporation|isbn=9780486642352|language=en}}
12. ^{{cite book|last1=Berzelius|first1=Jacob|title=Jahres-Bericht über die Fortschritte der Chemie und Mineralogie (Annual Report on the Progress of Chemistry and Mineralogy)|date=1848|publisher=Laupp|location=Tübigen, (Germany)|volume=vol. 47|page=654|url=https://books.google.com/books?id=mDc4AQAAIAAJ&dq=%22glycin%22&pg=PA654#v=onepage&q=%22glycin%22&f=false}} 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. ^{{Cite book|url=https://books.google.com/books?id=qKjxtZvnBKQC&pg=PA141|title=Before Big Science: The Pursuit of Modern Chemistry and Physics, 1800-1940|last=Nye|first=Mary Jo|date=1999|publisher=Harvard University Press|isbn=9780674063822|language=en}}
14. ^{{cite web |url=http://oxforddictionaries.com/definition/american_english/glycine |title=glycine |work=Oxford Dictionaries |accessdate=2015-12-06}}
15. ^{{cite journal|last1=Cahours|first1=A.|title=Recherches sur les acides amidés|journal=Comptes Rendus|date=1858|volume=46|pages=1044–1047|url=https://babel.hathitrust.org/cgi/pt?id=umn.31951d00008355e;view=1up;seq=1050|trans-title=Investigations into aminated acids|language=French}}
16. ^{{Cite book|url=https://books.google.com/books?id=PTm1CwAAQBAJ&pg=PA385|title=Modern Industrial Microbiology and Biotechnology|last=Okafor|first=Nduka|date=2016-03-09|publisher=CRC Press|isbn=9781439843239|language=en}}
17. ^{{OrgSynth | first1 = A. W. | last1 = Ingersoll | first2 = S. H. | last2 = Babcock | title = Hippuric acid | prep=cv2p0328 | volume = 12 | pages = 40 | year = 1932 | collvol = 2 | collvolpages = 328}}
18. ^{{Cite book|url=https://books.google.com/books?id=f--1V1ftgtsC&pg=PA38|title=Kirk-Othmer Food and Feed Technology, 2 Volume Set|last=Wiley|date=2007-12-14|publisher=John Wiley & Sons|isbn=9780470174487|language=en}}
19. ^{{cite web |url=http://www.usitc.gov/trade_remedy/731_ad_701_cvd/investigations/2007/glycine_from_india_japan_korea/preliminary/DOC/Glycine%20Conference%20%28prelim%29.wpd |title=Glycine Conference (prelim) |publisher=USITC |date= |accessdate=2014-06-13 |deadurl=bot: unknown |archiveurl=https://web.archive.org/web/20120222063555/http://www.usitc.gov/trade_remedy/731_ad_701_cvd/investigations/2007/glycine_from_india_japan_korea/preliminary/DOC/Glycine%20Conference%20%28prelim%29.wpd |archivedate=2012-02-22 |df= }}
20. ^Drauz, Karlheinz; Grayson, Ian; Kleemann, Axel; Krimmer, Hans-Peter; Leuchtenberger, Wolfgang and Weckbecker, Christoph (2007) "Amino Acids" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim. {{DOI|10.1002/14356007.a02_057.pub2}}
21. ^Hart, J. Roger (2005) "Ethylenediaminetetraacetic Acid and Related Chelating Agents" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim. {{DOI|10.1002/14356007.a10_095}}
22. ^{{cite journal|title=A weak link in metabolism: the metabolic capacity for glycine biosynthesis does not satisfy the need for collagen synthesis|journal=Journal of Biosciences|volume=34|issue=6|pages=853–72|date=December 2009|pmid=20093739|author1=Meléndez-Hevia|first1=E|last2=De Paz-Lugo|first2=P|last3=Cornish-Bowden|first3=A|last4=Cárdenas|first4=M. L.|doi=10.1007/s12038-009-0100-9}}
23. ^1 {{cite journal| author = Hahn RG| year = 1993| title = Dose-dependent half-life of glycine| journal = Urological Research| volume = 21| issue = 4| pages = 289–291| doi = 10.1007/BF00307714| pmid = 8212419}}
24. ^1 2 3 4 5 6 {{Lehninger4th|pages=127, 675–77, 844, 854}}
25. ^{{Cite journal |last=Szpak |first=Paul |title=Fish bone chemistry and ultrastructure: implications for taphonomy and stable isotope analysis | url=https://uwo.academia.edu/PaulSzpak/Papers/827788/Fish_Bone_Chemistry_and_Ultrastructure_Implications_for_Taphonomy_and_Stable_Isotope_Analysis |journal=Journal of Archaeological Science |year=2011 |volume=38 |issue=12 |pages=3358–3372 |doi=10.1016/j.jas.2011.07.022 }}
26. ^{{cite web |url=http://www.cmj.org/Periodical/paperlist.asp?id=LW7347&linkintype=pubmed |title=Recent development in NMDA receptors |year=2000 |publisher=Chinese Medical Journal}}
27. ^{{cite web |url=http://physchem.ox.ac.uk/MSDS/GL/glycine.html |title=Safety (MSDS) data for glycine |year=2005 |publisher= The Physical and Theoretical Chemistry Laboratory Oxford University |accessdate=2006-11-01}}
28. ^{{cite web|url=http://www.usitc.gov/publications/701_731/pub3980.pdf |title=Glycine From Japan and Korea |date= January 2008|accessdate=2014-06-13|publisher=U.S. International Trade Commission}}
29. ^{{Cite journal|last=Kurtis|first=Frank|last2=Kamal|first2=Patel|last3=Gregory|first3=Lopez|last4=Bill|first4=Willis|date=2017-08-01|title=Glycine Research Analysis|url=https://examine.com/supplements/glycine/|journal=Examine.com}}
30. ^[https://www.federalregister.gov/documents/2007/11/07/E7-21873/notice-of-preliminary-determination-of-sales-at-less-than-fair-value-glycine-from-india "Notice of Preliminary Determination of Sales at Less Than Fair Value: Glycine From India"] Federal Register 72 (7 November 2007): 62827.
31. ^{{Cite book|url=https://books.google.com/books?id=z5-tDAAAQBAJ&pg=PA268|title=Liquid Phase Aerobic Oxidation Catalysis: Industrial Applications and Academic Perspectives|last=Stahl|first=Shannon S.|last2=Alsters|first2=Paul L.|date=2016-07-13|publisher=John Wiley & Sons|isbn=9783527690152|language=en}}
32. ^{{Cite web|url=https://www.tjchem.com.sg/glycine-fcc-iv|title=Glycine FCC IV {{!}} 56-40-6 {{!}} C2H5NO2 {{!}} T&J Chemicals|website=Speciality Chemicals Supply {{!}} T&J Chemicals|language=en|access-date=2018-09-17}}
33. ^{{Cite journal|last=Eaton|first=Scott J.|last2=Harakas|first2=George N.|last3=Kimball|first3=Richard W.|last4=Smith|first4=Jennifer A.|last5=Pilot|first5=Kira A.|last6=Kuflik|first6=Mitch T.|last7=Bullard|first7=Jeremy M.|date=2014-05-29|title=Formulation and Combustion of Glycerol–Diesel Fuel Emulsions|journal=Energy & Fuels|language=EN|volume=28|issue=6|pages=3940–3947|doi=10.1021/ef500670d|issn=0887-0624}}
34. ^{{cite journal |title=Evidence for extraterrestrial amino-acids and hydrocarbons in the Murchison meteorite |last=Kvenvolden |first=Keith A. |last2=Lawless |first2=James |last3=Pering |first3=Katherine |last4=Peterson |first4=Etta |last5=Flores |first5=Jose |last6=Ponnamperuma |first6=Cyril |last7=Kaplan |first7=Isaac R. |last8=Moore |first8=Carleton |journal=Nature |volume=228 |issue=5275 |pages=923–926 |year=1970|doi=10.1038/228923a0 |pmid=5482102 |bibcode=1970Natur.228..923K }}
35. ^{{cite news |url=https://www.reuters.com/article/scienceNews/idUSTRE57H02I20090818 |author=Reuters|title=Building block of life found on comet - Thomson Reuters 2009 |accessdate=2009-08-18 | date=18 August 2009}}
36. ^{{cite news |url= http://sci.esa.int/rosetta/57858-rosettas-comet-contains-ingredients-for-life/ |author=European Space Agency|title=Rosetta’s comet contains ingredients for life |accessdate=2016-06-05 | date=27 May 2016}}
37. ^{{cite journal |vauthors=Snyder LE, Lovas FJ, Hollis JM, etal |title=A rigorous attempt to verify interstellar glycine |journal=Astrophys J |volume=619 |issue=2 |pages=914–930 |year=2005 |doi=10.1086/426677 |bibcode=2005ApJ...619..914S | arxiv = astro-ph/0410335}}
38. ^{{cite web |url=https://www.sciencedaily.com/releases/2008/03/080326161658.htm |author=Staff|title=Organic Molecule, Amino Acid-Like, Found In Constellation Sagittarius 27 March 2008 - Science Daily |accessdate=2008-09-16}}
39. ^{{Cite journal|title=National Nutrient Database for Standard Reference |url=http://www.nal.usda.gov/fnic/foodcomp/search/ |publisher=U.S. Department of Agriculture |accessdate=2009-09-07 |deadurl=yes |archiveurl=https://web.archive.org/web/20150303000000/http://www.nal.usda.gov/fnic/foodcomp/search/ |archivedate=2015-03-03 |df= }}

Further reading

  • {{cite journal |vauthors=Kuan YJ, Charnley SB, Huang HC, etal |title=Interstellar glycine |journal=Astrophys J |volume=593 |issue=2 |pages=848–867 |year=2003 |doi=10.1086/375637 |bibcode=2003ApJ...593..848K}}
  • {{cite web |url=https://www.newscientist.com/news/news.jsp?id=ns99992558 |author=Rachel Nowak |title=Amino acid found in deep space - 18 July 2002 - New Scientist |accessdate=2007-07-01}}

External links

{{commons category}}
  • Glycine MS Spectrum
  • Glycine at PDRHealth.com
  • Glycine cleavage system
  • Glycine Therapy - A New Direction for Schizophrenia Treatment?
  • {{cite journal | title = Organic Molecule, Amino Acid-Like, Found In Constellation Sagittarius | journal = ScienceDaily |date=27 March 2008| url = https://www.sciencedaily.com/releases/2008/03/080326161658.htm}}
  • {{cite journal | journal = Psychiatric Times | volume = 25 | issue = 14 | title = A New Class of Antipsychotic Drugs: Enhancing Neurotransmission Mediated by NMDA Receptors | author = Guochuan E. Tsai |date=1 December 2008| url = http://www.psychiatrictimes.com/display/article/10168/1357569}}
  • ChemSub Online (Glycine).
  • NASA scientists have discovered glycine, a fundamental building block of life, in samples of comet Wild 2 returned by NASA's Stardust spacecraft.
{{Amino acids}}{{Amino acid metabolism intermediates}}{{Neurotransmitters}}{{Glycine receptor modulators}}{{Ionotropic glutamate receptor modulators}}{{Molecules detected in outer space}}{{Authority control}}

7 : Flavor enhancers|Glucogenic amino acids|Neurotransmitters|Proteinogenic amino acids|Glycine receptor agonists|NMDA receptor agonists|E-number additives
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