6208-95-3

Basic information

• Product Name: L-2-Methylglutamic acid
• Synonyms: L-2-Methylglutamic acid;L-2-Me-Glu-OH;L-Glutamic acid, 2-methyl-;alpha-Methyl-L-glutamic acid;L-alpha-Methylglutamic acid
• CAS NO: 6208-95-3
• Molecular Formula: C6H11NO4
• Molecular Weight: 161.15584
• Mol File: 6208-95-3.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: L-2-Methylglutamic acid(CAS DataBase Reference)
• NIST Chemistry Reference: L-2-Methylglutamic acid(6208-95-3)
• EPA Substance Registry System: L-2-Methylglutamic acid(6208-95-3)

Safety Data

• Hazardous Substances Data: 6208-95-3(Hazardous Substances Data)

Usage

General Description

L-2-Methylglutamic acid is a naturally occurring amino acid derivative that plays a role in the regulation of glutamate metabolism and neurotransmission. It is a known inhibitor of glutamate decarboxylase, an enzyme responsible for the synthesis of the inhibitory neurotransmitter gamma-aminobutyric acid (GABA). L-2-Methylglutamic acid has also been studied for its potential applications in the treatment of neurological disorders, as well as its role in the modulation of glutamate receptors, which are involved in synaptic transmission and plasticity in the central nervous system. L-2-Methylglutamic acid has shown promise in research and may have therapeutic potential for conditions related to glutamate dysregulation.

Upstream product

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Relevant articles and documents

Synthesis of optically active, unnatural α-substituted glutamic acid derivatives by a chiral calcium-catalyzed 1,4-addition reaction

The first catalytic asymmetric 1,4-addition reactions of azlactones with acrylic esters have been developed. A chiral coordinative calcium catalyst was found to be effective for these reactions, and the desired 1,4-adducts were obtained in good yields and enantioselectivities. The product was converted to the corresponding α-alkylated glutamic acid by acid hydrolysis.

Asymmetric synthesis of α-Methyl α-Amino Acids through diastereoselective alkylation under mild reaction conditions of an iminic alanine template with a 1,2,3,6-Tetrahydro-2-Pyrazinone structure

(6R)-6-Isopropyl-3-methyl-5-phenyl-1,2,3,6-tetrahydro-2-pyrazinone, obtained from (R)-valine and (S)-alanine, is highly diastereoselectively alkylated at room temperature by: a) activated alkyl halides under solid-liquid PTC conditions, b) non-activated alkyl halides with organic bases, c) electrophilic olefins employing both solid-liquid PTC conditions and organic bases, and d) allylic carbonates by means of palladium catalysis under neutral conditions. Enantiomerically pure (S)-α-methyl α-amino acids 8 are obtained by hydrolysis of the alkylated pyrazinones.

New chiral alanine template with a 1,2,3,6-tetrahydro-2-pyrazinone structure for the asymmetric synthesis of α-methyl α-amino acids

(R)-6-Isopropyl-5-phenyl- 1,2,3,6-tetrahydro-2-pyrazinone, prepared from (R)-valine and (S)-alanine, reacts With activated alkyl halides and electrophilic olefins under solid-liquid PTC conditions: with K2CO3 as base, at room temperature and with high diastereoselectivity (>94%). The palladium-catalyzed allylation reaction of this alanine derivative under neutral conditions at room temperature also takes place with a de>96%. Final hydrolysis of alkylated pyrazinones affords enantiomerically pure α-methyl α-amino acids.