gamma-Glutamylmethylamide
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| Names | |
|---|---|
| IUPAC name
(2S)-2-amino-5-(methylamino)-5-oxopentanoic acid | |
| Other names
N-Methyl-L-glutamine; metheanine | |
| Identifiers | |
3081-62-7  | |
| ChEBI | CHEBI:58200 |
| ChemSpider | 388957 |
| DrugBank | DB03473 |
| Jmol interactive 3D | Image |
| KEGG | C03153 |
| PubChem | 439925 |
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| Properties | |
| C6H12N2O3 | |
| Molar mass | 160.17 g/mol |
| Density | 1.211 g/mL |
| Boiling point | 427.5 °C (801.5 °F; 700.6 K) |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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| Infobox references | |
γ-Glutamylmethylamide (gamma-Glutamylmethylamide, abbrev. GMA, synonyms N-methyl-L-glutamine, metheanine) is an amino acid analog of the proteinogenic amino acids L-glutamic acid and L-glutamine, found primarily in plant and fungal species; simply speaking, it is L-glutamine methylated on the amide nitrogen. It is an identified an important biosynthetic intermediate allowing bacteria (e.g., methanotrophs) use of methylated amines as carbon and nitrogen source for growth (and so of significant biotechnological interest).[1][2][3] Like its close relative theanine, it is a pharmacologically active constituent of green tea, with preliminary evidence for at least comparable activity to theanine as a hypotensive.[4]
See also
References
- ↑ Chen, Y; Scanlan, J; Song, L; Crombie, A; Rahman, MT; Schäfer, H; Murrell, JC (2010). "γ-Glutamylmethylamide is an essential intermediate in the metabolism of methylamine by Methylocella silvestris". Appl Environ Microbiol 76 (13): 4530–4537. doi:10.1128/AEM.00739-1. PMID 20472738.
- ↑ Wischer, D; Kumaresan, D; Johnston, A; El Khawand, M; Stephenson, J; Hillebrand-Voiculescu, AM; Chen, Y; Colin Murrell, J (2014). "Bacterial metabolism of methylated amines and identification of novel methylotrophs in Movile Cave". ISME J 9 (1): 195–206. doi:10.1038/ismej.2014.102. PMID 25050523.
- ↑ Xu, L; Gao, G; Wengen, C; Xu, J; Zhao, L; Shi, H; Zhang, X (2014). "Enzymatic synthesis of γ-glutamylmethylamide from glutamic acid γ-methyl ester and methylamine catalyzed by Escherichia coli having γ-glutamyltranspeptidase activity". Appl Biochem Biotechnol 173 (4): 851–6. doi:10.1007/s12010-014-0877-3. PMID 24733529.
- ↑ Yokogoshi H, Kobayashi M. (1998). "Hypotensive effect of gamma-glutamylmethylamide in spontaneously hypertensive rats.". Life Sci. 62 (12): 1065–8. doi:10.1016/S0024-3205(98)00029-0. PMID 9519808.
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