6141-27-1

Basic information

• Product Name: (2S,4S)-4-METHYLGLUTAMIC ACID
• Synonyms: (2S,4S)-4-METHYLGLUTAMIC ACID;(2S,4S)-(+)-2-AMINO-4-METHYLPENTANEDIOIC ACID;(4S)-4-Methyl-L-glutamic Acid;L-threo--Methylglutamate;L-threo--Methylglutamic Acid;threo-4-Methyl-L-glutamic Acid
• CAS NO: 6141-27-1
• Molecular Formula: C₆H₁₁NO₄
• Molecular Weight: 161.16
• Product Categories: Amino Acids 13C, 2H, 15N;Amino Acids & Derivatives;Chiral Reagents;Neurochemicals
• Mol File: 6141-27-1.mol

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: Methanol (Slightly), Water (Soluble)
• CAS DataBase Reference: (2S,4S)-4-METHYLGLUTAMIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4S)-4-METHYLGLUTAMIC ACID(6141-27-1)
• EPA Substance Registry System: (2S,4S)-4-METHYLGLUTAMIC ACID(6141-27-1)

Safety Data

• Hazardous Substances Data: 6141-27-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(2S,4S)-4-METHYLGLUTAMIC ACID is used as a potent and selective kainate receptor agonist for its ability to desensitize kainate receptors and attenuate capsaicin and inflammatory hyperalgesia. This makes it a valuable compound in the development of treatments for neurological disorders and pain management.
Used in Research Applications:
(2S,4S)-4-METHYLGLUTAMIC ACID is used as a research tool for studying the function and mechanisms of metabotropic receptors, contributing to a better understanding of their role in various physiological and pathological processes.

Upstream product

• 1030836-20-4 dimethyl (2S,4S)-N-(tert-butoxycarbonyl)-4-methylglutamate 
• 7148-24-5 diethyl (4-nitrobenzoyl)-L-glutamate 
• 260545-98-0 (+) dimethyl (S)-2,2-dimethoxy-4-methylglutarate 
• 260545-97-9 (R,S)-dimethyl 2,2-dimethoxy-4-methylglutarate 
• 261159-33-5 dimethyl (S)-4-methyl-2-oxoglutarate 
• 4469-60-7 dimethyl 2,2-dimethoxypentanedioate 
• 328-50-7 α-ketoglutaric acid 
• 553679-44-0 ethyl (2S,4S)-N-tert-butoxycarbonyl-4-methylpyroglutamate 
• 7149-65-7 ethyl (S)-pyroglutamate 
• 98-79-3 L-Pyroglutamic acid 
• 4931-66-2 methyl (S)-pyroglutamate 
• 196394-48-6 (2S,4S)-1-tert-butyl 2-methyl 4-methyl-5-oxopyrrolidine-1,2-dicarboxylate 
• 144978-35-8 (S)-ethyl N-tert-butoxycarbonylpyroglutamate 
• 108963-96-8 (S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one 

Downstream Products

• 31137-74-3 (2S,4R)-4-methylglutamic acid 
• 42453-21-4 4-Amino-2-methylbutyric acid 

Relevant articles and documents

A Versatile Boc Solid Phase Synthesis of Daptomycin and Analogues Using Site Specific, On-Resin Ozonolysis to Install the Kynurenine Residue

A de novo solid-phase synthesis of the cyclic lipodepsipeptide daptomycin via Boc chemistry was achieved. The challenging ester bond formation between the nonproteinogenic amino acid kynurenine was achieved by esterification of a threonine residue with a

Chemoenzymatic synthesis of glutamic acid analogues: Substrate specificity and synthetic applications of branched chain aminotransferase from Escherichia coli

(Chemical Equation Presented) A new route to α-keto acids is described, based on the ozonolysis of enol acetates obtained from α-substituted β-keto esters. Escherichia coli branched chain aminotransferase (BCAT) activity toward a variety of substituted 2-oxoglutaric acids was demonstrated analytically. BCAT was shown to have a broad substrate spectrum, complementary to that of aspartate aminotransferase, and to offer access to a variety of glutamic acid analogues. The usefulness of BCAT was demonstrated through the synthesis of several 3- and 4-substituted derivatives.

A concise synthesis of (2S,4R)- and (2S,4S)-4-methylglutamic acid

A concise, multi-gram scale method for producing the bioactive and enantiomerically pure epimers, (2S,4R)- and (2S,4S)-glutamic acids, in a single synthetic scheme is described.

2,8'-Disubstituted-1,1'-Binaphthyls: A New Pattern in Chiral Ligands

The title binaphthyls 19 and 26, which are the positional isomers of 2-methoxy-2'-(diphenylphosphino)-1,1'-binaphthyl (MOP, 19) and 2-amino-2'-hydroxy-1,1'-binaphthyl (NOBIN, 26), have been synthesized by Suzuki coupling as the key step (10 + 15 -> 18), followed by functional group transformations, involving C-P and C-N bond formation (18 -> 19 and 18 -> 23). Racemic intermediate 22 was resolved by cocrystallization with N-benzylcinchonidinium chloride and the absolute configuration determined by X-ray crystallography. These novel binaphthyls are configurationally stable and, as such, potentially usable as chiral ligands in asymmetric reactions. Michael addition of the glycine-derived enolate 40 to methyl acrylate, carried out in the presence of (R)-(-)-27 as the chiral phase-transfer catalyst, afforded L-glutamic acid (S)-(+)-43 of 92% ee (after hydrolysis of the primary product).

Synthesis of 4,4-Disubstituted L-Glutamic Acids by Enzymatic Transamination

The syntheses of optically pure 4,4-dimethyl-L-glutamic acid as well as (2S,4R)- and (2S,4S)-4-hydroxy-4-methylglutamic acids have been achieved by transamination of the corresponding 2-oxo-4,4-dimethyl- and rac-2-oxo-4-hydroxy-4-methylglutaric acids using glutamic oxalacetic transaminase (GOT).

Chemoenzymatic synthesis of (4S)- and (4R)-4-methyl-2-oxoglutaric acids, precursors of glutamic acid analogues

Alkylation of dimethyl 2,2-dimethoxyglutarate followed by enzymatic resolution afforded (4S)- and (4R)-4-methyl-2-oxoglutaric acid in an enantiomerically pure form. The activity of glutamic oxalacetic transaminase towards these compounds has been measured. Their enzymatic transamination provides an efficient synthesis of (4S)- and (4R)-4-methyl-L-glutamic acids which are very useful for characterisation of glutamate receptors in the central nervous system.

A convenient and efficient synthesis of (2S,4R)- and (2S,4S)-4-methylglutamic acid

Both enantiomerically pure (2S,4S)- and (2S,4R)-4-methylglutamic acids have been prepared in an overall 60% yield, by a convenient 7-step synthesis based on C-4 alkylation/epimerization of readily available (S)-pyroglutamic acid.

Resolution and regioselective protection of glutamic acid analogues. I- Resolution of diastereomeric α-boroxazolidone derivatives

Diastereomeric α-boroxazolidone γ-phenylethylamide (or γ-phenylethanolamide) derivatives of 2-, 3- or 4-substituted glutamic acid analogues have been separated by silicagel chromatography, resulting, after deprotection, in a practical method for the resolution of most of these unnatural amino acids.