N-Methyl-L-glutamic acid

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N-Methyl-l-glutamic acid
Names
IUPAC name
N-Methyl-L-glutamic acid
Systematic IUPAC name
(2S)-2-(Methylamino)pentanedioic acid
Other names
N-Methylglutamic acid; Methylglutamic acid; Methylglutamate
Identifiers
3D model (JSmol)
3DMet
ChEBI
ChemSpider
KEGG
UNII
  • InChI=1S/C6H11NO4/c1-7-4(6(10)11)2-3-5(8)9/h4,7H,2-3H2,1H3,(H,8,9)(H,10,11)/t4-/m0/s1
    Key: XLBVNMSMFQMKEY-BYPYZUCNSA-N
  • O=C(O)CC[C@H](NC)C(=O)O
Properties
C6H11NO4
Molar mass 161.157 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N-Methyl-l-glutamic acid (methylglutamate) is a chemical derivative of glutamic acid in which a methyl group has been added to the amino group. It is an intermediate in methane metabolism. Biosynthetically, it is produced from methylamine and glutamic acid by the enzyme methylamine—glutamate N-methyltransferase.[1] It can also be demethylated by methylglutamate dehydrogenase to regenerate glutamic acid.[2]

References

  1. ^ Shaw, WV; Tsai, L; Stadtman, ER (1966). "The enzymatic synthesis of N-methylglutamic acid". The Journal of Biological Chemistry. 241 (4): 935–45. doi:10.1016/S0021-9258(18)96855-9. PMID 5905132.
  2. ^ Hersh, LB; Stark, MJ; Worthen, S; Fiero, MK (1972). "N-methylglutamate dehydrogenase: Kinetic studies on the solubilized enzyme". Archives of Biochemistry and Biophysics. 150 (1): 219–26. doi:10.1016/0003-9861(72)90029-X. PMID 5028076.


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