gamma-Glutamylmethylamide

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]

gamma-Glutamylmethylamide

Names
IUPAC name (2S)-2-amino-5-(methylamino)-5-oxopentanoic acid
Other names N-Methyl-L-glutamine; metheanine
Identifiers
CAS Number	3081-62-7^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:58200^Y
ChemSpider	388957^Y
DrugBank	DB03473^Y
KEGG	C03153^Y
PubChem CID	439925
CompTox Dashboard (EPA)	DTXSID70953014
InChI InChI=1S/C6H12N2O3/c1-8-5(9)3-2-4(7)6(10)11/h4H,2-3,7H2,1H3,(H,8,9)(H,10,11)/t4-/m0/s1^Y Key: ONXPDKGXOOORHB-BYPYZUCNSA-N^Y InChI=1/C6H12N2O3/c1-8-5(9)3-2-4(7)6(10)11/h4H,2-3,7H2,1H3,(H,8,9)(H,10,11)/t4-/m0/s1 Key: ONXPDKGXOOORHB-BYPYZUCNBU
SMILES O=C(NC)CC[C@H](N)C(=O)O
Properties
Chemical formula	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).
Y verify (what is ^YN ?)
Infobox references

See also

• Theanine
• Health effects of tea

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. PMC 2897447. 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. PMC 4274414. 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.