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From the Grammy Nominated album The Truth About Love available now - http://smarturl.it/tal Music video by P!nk featuring Nate Ruess performing Just Give Me ...
Watch judges' comments at http://itv.com/XFactor (UK ONLY) Watch James Arthur sing Impossible by Shontelle Sweeeeet! As potential Winner's Singles go, this o...
Thrift Shop on iTunes: http://itunes.apple.com/us/album/thrift-shop-feat.-wanz-single/id556955707 The Heist physical deluxe edition: http://www.macklemoremer...
Music video by Rihanna performing Rehab. YouTube view counts pre-VEVO: 19591123. (C) 2007 The Island Def Jam Music Group.
Music video by Rihanna performing Russian Roulette. (C) 2009 The Island Def Jam Music Group.
So i was pretty hesitant to make this video... but after all of your request, here is my Draw My Life video! Check out my 2nd Channel for more vlogs: http://...
Download "Stay" from Unapologetic now: http://smarturl.it/UnapologeticDlx Music video by Rihanna performing Stay ft. Mikky Ekko. © 2013 The Island Def Jam Mu...
YOLO is available on iTunes now! http://smarturl.it/lonelyIslandYolo THE LONELY ISLAND - THE WACK ALBUM - JUNE 11th! Pre-order THE WACK ALBUM DIRECT: http://...
For you nosy people, this is the reason why Selena Gomez broke up with Justin Bieber. Get the song on iTunes: http://bit.ly/T74XEZ Andy Lange produced the mu...
Play the DUDE PERFECT GAME here! iPhone - http://bit.ly/DPGameiPhone Android - http://bit.ly/DPGameAndroid iPad - http://bit.ly/DPGameiPad Tweet! http://bit....
Don't be these people. Mapoti See Bloopers and Behind-The-Scenes Here!: http://youtu.be/dfpo7uXwJnM Huge thank you and shout out to Dtrix: http://www.youtube...
Macklemore & Ryan Lewis present the official music video for Can't Hold Us feat. Ray Dalton. Can't Hold Us on iTunes: https://itunes.apple.com/us/album/cant-...
This video accidentally turned out kind of sad, ME SO SOWWY IT NOT POSED TO BE SAD WHO WANTS HUGS AND COOKIES? Also, FYI for anyone attempting this, it takes...
Pre-order new album Unapologetic, out worldwide Monday, November 19: http://smarturl.it/UnapologeticDlx Music video by Rihanna performing Diamonds. ©: The Is...
Music video by Rihanna performing Pon de Replay. YouTube view counts pre-VEVO: 4166822. (C) 2005 The Island Def Jam Music Group.
What people expect romance to be vs what it really is... Follow Catherine! https://twitter.com/CDekoekkoek Check out my 2nd Channel for more vlogs: http://ww...
Its a simple math equation really... Click to see Bloopers and The making of this video here!: http://www.youtube.com/watch?v=nccOGxj27J8 Follow me on TWITTE...
Please take a second and LIKE+FAV this video! :D I worked really hard on it. Also : SHARE THIS VIDEO with friends:) Twitter/Facebook/Websites *brofist* More ...
BLOOPERS & PAC MAN+PONG: http://bit.ly/vg2XTRAS WATCH EN ESPAÑOL: http://youtu.be/Os1npZHzudw WATCH PART 1 w/ SUPER MARIO, ZELDA, + MORE: http://youtu.be/9bK...
Buy on iTunes: http://www.Smarturl.it/TTT Amazon: http://idj.to/svJVGM Music video by Rihanna performing Where Have You Been. ©: The Island Def Jam Music Group.
|Jmol-3D images||Image 1|
|Molar mass||75.07 g mol−1|
233 °C (decomposition)
|Solubility in water||24.99 g/100 mL (25 °C)|
|Solubility||soluble in ethanol, pyridine
insoluble in ether
|Acidity (pKa)||2.34 (carboxyl), 9.6 (amino)|
|LD50||2600 mg/kg (mouse, oral)|
|Supplementary data page|
|n, εr, etc.|
Solid, liquid, gas
|Spectral data||UV, IR, NMR, MS|
| (what is: / ?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Glycine (abbreviated as Gly or G) is an organic compound with the formula NH2CH2COOH. Having a hydrogen substituent as its side-chain, glycine is the smallest of the 20 amino acids commonly found in proteins. Its codons are GGU, GGC, GGA, GGG cf. the genetic code.
Glycine is a colourless, sweet-tasting crystalline solid. It is unique among the proteinogenic amino acids in that it is not chiral. It can fit into hydrophilic or hydrophobic environments, due to its minimal side chain of only one hydrogen atom. Glycine is also the genus name of the Soybean plant (species name = Glycine max).
Production and key properties 
- ClCH2COOH + 2 NH3 → H2NCH2COOH + NH4Cl
About 15 million kg are produced annually in this way.
There are two producers of glycine in the United States: Chattem Chemicals, Inc., a subsidiary of Mumbai-based Sun Pharmaceutical, and GEO Specialty Chemicals, Inc., which purchased the glycine and naphthalene sulfonate production facilities of Hampshire Chemical Corp, a subsidiary of Dow Chemical.
Chattem's manufacturing process ("MCA" process) occurs in batches and results in a finished product with some residual chloride but no sulfate, while GEO’s manufacturing process is considered a semi-batch process and results in a finished product with some residual sulfate but no chloride.
Its pKA values are 2.35 and 9.78, so above pH 9.78, most of the glycine exists as the anionic amine, H2NCH2CO2-. Below pH 2.35, its solutions contain mostly the cationic carboxylic acid H3N+CH2CO2H. Its isoelectric point (pI) is 6.06.
Glycine exists in zwitterionic form in solution. In this form, the partial charges on different atoms as determined using Gasteiger charge method are given as follows: N (+0.2358), H (attached to N) (+0.1964), alpha-C (+0.001853), H (attached to alpha-C) (+0.08799), carbonyl C (+0.085) and carbonyl O (-0.5445).
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. In most organisms, the enzyme Serine hydroxymethyltransferase catalyses this transformation via the cofactor pyridoxal phosphate:
- serine + tetrahydrofolate → glycine + N5,N10-Methylene tetrahydrofolate + H2O
- CO2 + NH4+ + N5,N10-Methylene tetrahydrofolate + NADH + H+ → Glycine + tetrahydrofolate + NAD+
- Glycine + tetrahydrofolate + NAD+ → CO2 + 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.
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.
The half-life of glycine and its elimination from the body varies significantly based on dose. In one study, the half-life was between 0.5 and 4.0 hours. 
Physiological function 
The principal function of glycine is as a precursor to proteins. It is also a building block to numerous natural products.
As a biosynthetic intermediate 
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) glutaminergic receptors which are excitatory. The LD50 of glycine is 7930 mg/kg in rats (oral), and it usually causes death by hyperexcitability.
Commercial uses 
In the US, glycine is typically sold in two grades: United States Pharmacopeia (“USP”), and technical grade. Most glycine is manufactured as USP grade material for diverse uses. USP grade sales account for approximately 80 to 85 percent of the U.S. market for glycine.
- Pharmaceutical grade glycine is produced for some pharmaceutical applications, such as intravenous injections, where the customer’s purity requirements often exceed the minimum required under the USP grade designation. Pharmaceutical grade glycine is often produced to proprietary specifications and is typically sold at a premium over USP grade glycine.
- Technical grade glycine, which may or may not meet USP grade standards, is sold for use in industrial applications; e.g., as an agent in metal complexing and finishing. Technical grade glycine is typically sold at a discount to USP grade glycine.
Animal and human foods 
Other markets for USP grade glycine include its use an additive in pet food and animal feed. For humans, glycine is sold as a sweetener/taste enhancer. Certain food supplements and protein drinks contain glycine. Certain drug formulations include glycine to improve gastric absorption of the drug.
Cosmetics and miscellaneous applications 
Many miscellaneous products use glycine or its derivatives, such as the production of rubber sponge products, fertilizers, metal complexants.
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. Glyphosate is a non-selective systemic herbicide used to kill weeds, especially perennials and broadcast or used in the cut-stump treatment as a forestry herbicide. Initially, glyphosate was sold only by Monsanto under the tradename Roundup, but is no longer under patent.
Presence in space 
The detection of glycine in the interstellar medium has been debated. In 2008, the glycine-like molecule aminoacetonitrile was discovered in the Large Molecule Heimat, a giant gas cloud near the galactic center in the constellation Sagittarius by the Max Planck Institute for Radio Astronomy. In 2009, glycine sampled in 2004 from comet Wild 2 by the NASA spacecraft Stardust was confirmed, the first discovery of extraterrestrial glycine. That mission's results bolstered the theory of panspermia, which claims that the "seeds" of life are widespread throughout the universe.
See also 
- The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (11th ed.), Merck, 1989, ISBN 091191028X, 4386.
- Dawson, R.M.C., et al., Data for Biochemical Research, Oxford, Clarendon Press, 1959.
- "Nomenclature and symbolism for amino acids and peptides (IUPAC-IUB Recommendations 1983)", Pure Appl. Chem. 56 (5), 1984: 595–624, doi:10.1351/pac198456050595.
- R.H.A. Plimmer (1912) . In R.H.A. Plimmer & F.G. Hopkins. The chemical composition of the proteins. Monographs on biochemistry. Part I. Analysis (2nd ed.). London: Longmans, Green and Co. p. 82. Retrieved January 18, 2010.
- Ingersoll, A. W.; Babcock, S. H. (1932), "Hippuric acid", Org. Synth. 12: 40; Coll. Vol. 2: 328.
- Karlheinz Drauz, Ian Grayson, Axel Kleemann, Hans-Peter Krimmer, Wolfgang Leuchtenberger, Christoph Weckbecker “Amino Acids” in Ullmann's Encyclopedia of Industrial Chemistry 2007, Wiley-VCH, Weinheim. doi:10.1002/14356007.a02_057.pub2
- U.S. International Trade Commission, "Glycine From China." Investigation No. 731-TA-718 (Second Review), Publication No. 3810, October 2005
- 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.
- Szpak, Paul (2011). "Fish bone chemistry and ultrastructure: implications for taphonomy and stable isotope analysis". Journal of Archaeological Science 38 (12): 3358–3372. doi:10.1016/j.jas.2011.07.022.
- Hahn RG (1993). "Dose-dependent half-life of glycine". Urological Research 21 (4): 289–291. doi:10.1007/BF00307714. PMID 8212419.
- "Recent development in NMDA receptors". Chinese Medical Journal. 2000.
- "Safety (MSDS) data for glycine". The Physical and Theoretical Chemistry Laboratory Oxford University. 2005. Retrieved 2006-11-01.
- Yamadera W, Inagawa K, Chiba S, Bannai M, Takahashi M, Nakayama K (2007). "Glycine ingestion improves subjective sleep quality in human volunteers, correlating with polysomnographic changes". Sleep and Biological rhythms 5 (2): 126–131. doi:10.1111/j.1479-8425.2007.00262.x.
- "Notice of Preliminary Determination of Sales at Less Than Fair Value: Glycine From India" Federal Register 72 (7 November 2007): 62827.
- 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. Bibcode:2005ApJ...619..914S. doi:10.1086/426677.
- Staff. "Organic Molecule, Amino Acid-Like, Found In Constellation Sagittarius 27 March 2008 - Science Daily". Retrieved 2008-09-16.
- Reuters (18 August 2009). "Building block of life found on comet - Thomson Reuters 2009". Retrieved 2009-08-18.
Further reading 
On attempts to detect glycine in interstellar medium
- Kuan YJ, Charnley SB, Huang HC, et al. (2003). "Interstellar glycine". Astrophys J 593 (2): 848–867. Bibcode:2003ApJ...593..848K. doi:10.1086/375637.
- Rachel Nowak. "Amino acid found in deep space - 18 July 2002 - New Scientist". Retrieved 2007-07-01.
- Glycine at PDRHealth.com
- Glycine cleavage system
- Glycine Therapy - A New Direction for Schizophrenia Treatment?
- "Organic Molecule, Amino Acid-Like, Found In Constellation Sagittarius". ScienceDaily. 27 March 2008.
- Guochuan E. Tsai (1 December 2008). "A New Class of Antipsychotic Drugs: Enhancing Neurotransmission Mediated by NMDA Receptors". Psychiatric Times 25 (14).
- 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.