Glycine[1] | |
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Glycine |
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Other names
Aminoethanoic acid |
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Identifiers | |
Abbreviations | Gly, G |
CAS number | 56-40-6 |
PubChem | 750 |
ChemSpider | 730 |
UNII | TE7660XO1C |
EC-number | 200-272-2 |
DrugBank | DB00145 |
KEGG | D00011 |
ChEBI | CHEBI:15428 |
ChEMBL | CHEMBL773 |
IUPHAR ligand | 727 |
Jmol-3D images | Image 1 |
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Properties | |
Molecular formula | C2H5NO2 |
Molar mass | 75.07 g mol−1 |
Appearance | white solid |
Density | 1.607 g/cm3 |
Melting point |
233 °C (decomposition) |
Solubility in water | 24.99 g/100 mL (25 °C)[2] |
Solubility | soluble in ethanol, pyridine insoluble in ether |
Acidity (pKa) | 2.34 (carboxyl), 9.6 (amino)[3] |
Hazards | |
MSDS | External MSDS |
LD50 | 2600 mg/kg (mouse, oral) |
Supplementary data page | |
Structure and properties |
n, εr, etc. |
Thermodynamic data |
Phase behaviour Solid, liquid, gas |
Spectral data | UV, IR, NMR, MS |
(verify) (what is: / ?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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Infobox references |
Glycine (abbreviated as Gly or G)[4] 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 two hydrogen atom side chain.
Contents |
Glycine was discovered in 1820, by Henri Braconnot who boiled gelatin with sulfuric acid.[5]
Glycine is manufactured industrially by treating chloroacetic acid with ammonia:[6]
About 15 million kg are produced annually in this way.[7]
In the USA (by GEO Specialty Chemicals, Inc.) and in Japan (by Shoadenko), glycine is produced via the Strecker amino acid synthesis.[8]
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.[8][9]
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:[10]
In the liver of vertebrates, glycine synthesis is catalyzed by glycine synthase (also called glycine cleavage enzyme). This conversion is readily reversible:[10]
Glycine is coded by codons GGU, GGC, GGA and GGG. Most proteins incorporate only small quantities of glycine. A notable exception is collagen, which contains about 35% glycine.[10][11]
Glycine is degraded via three pathways. The predominant pathway in animals involves the catalysis of glycine cleavage enzyme, the same enzyme also involved in the biosynthesis of glycine. The degradation pathway is the reverse of this synthetic pathway:[10]
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.[10]
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.[10]
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. [12]
The principal function of glycine is as a precursor to proteins. It is also a building block to numerous natural products.
In higher eukaryotes, D-Aminolevulinic acid, the key precursor to porphyrins, is biosynthesized from glycine and succinyl-CoA. Glycine provides the central C2N subunit of all purines.[10]
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),[13] and it usually causes death by hyperexcitability.
There is some evidence showing that 3000 milligrams of glycine before bedtime improves sleep quality.[14]
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.
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. Food supplements and protein drinks contain glycine. Certain drug formulations include glycine to improve gastric absorption of the drug.
Glycine serves as a buffering agent in antacids, analgesics, antiperspirants, cosmetics, and toiletries.
Many miscellaneous products use glycine or its derivatives, such as the production of rubber sponge products, fertilizers, metal complexants.[16]
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.
The detection of glycine in the interstellar medium has been debated.[17] 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.[18] 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.[19]
On attempts to detect glycine in interstellar medium
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