gamma-Glutamylmethylamide

gamma-Glutamylmethylamide

gamma-Glutamylmethylamide
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
ChEBI	CHEBI:58200 Y
ChemSpider	388957 Y
DrugBank	DB03473 Y
Jmol 3D model	Interactive image
KEGG	C03153 Y
PubChem	439925
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).
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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). 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.

See also

• Theanine
• Health effects of tea