gamma-Glutamylmethylamide

gamma-Glutamylmethylamide
Names
IUPAC name
(2S)-2-amino-5-(methylamino)-5-oxopentanoic acid
Other names
N-Methyl-L-glutamine; metheanine
Identifiers
3081-62-7 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:58200 YesY
ChemSpider 388957 YesY
DrugBank DB03473 YesY
KEGG C03153 YesY
PubChem 439925
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

  1. 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.00739-10. PMID 20472738.
  2. 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.
  3. 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.
  4. 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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