γ-Glutamylmethylamide

γ-Glutamylmethylamide
Names
	IUPAC name N-Methyl-L-glutamine
	Systematic IUPAC name (2S)-2-Amino-5-(methylamino)-5-oxopentanoic acid
	Other names Metheanine
Identifiers
CAS Number	3081-62-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:58200 ;
ChemSpider	388957 ;
DrugBank	DB03473 ;
KEGG	C03153 ;
PubChem CID	439925;
UNII	2N7NDF57QD ;
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 Key: ONXPDKGXOOORHB-BYPYZUCNSA-N ; 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). verify (what is ?) 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.^{[citation needed]} It is an identified 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]^{[non-primary source needed]} 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]^{[non-primary source needed]}

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. Bibcode:2010ApEnM..76.4530C. doi:10.1128/AEM.00739-10. PMC 2897447. 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. PMC 4274414. 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. S2CID 19699395.
^ 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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[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. Bibcode:2010ApEnM..76.4530C. 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. S2CID 19699395.

[Hypotensive-Yokogoshi-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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See also

References