31137-74-3

Basic information

• Product Name: (2S,4R)-4-METHYLGLUTAMIC ACID
• Synonyms: SYM 2081;ERYTHRO-4-METHYL-L-GLUTAMIC ACID;(2S,4R)-(+)-2-Amino-4-methylpentanedioic acid;(2S,4R)-4-METHYLGLUTAMIC ACID;(2S,4R)-(+)-2-AMINO-4-METHYLPENTANEDIOIC ACID 99%;(2S-R)-4-METHYLGLUTAMIC ACID;(4R)- 4-Methyl-L-glutamic Acid;erythro-L-4-Methylglutamic Acid
• CAS NO: 31137-74-3
• Molecular Formula: C₆H₁₁NO₄
• Molecular Weight: 161.16
• Product Categories: Amino Acids 13C, 2H, 15N;Amino Acids & Derivatives;Chiral Reagents;Neurochemicals
• Mol File: 31137-74-3.mol

Chemical Properties

• Melting Point: 178 °C
• Boiling Point: 287.44°C (rough estimate)
• Flash Point: 153°C
• Appearance: white/solid
• Density: 1.3482 (rough estimate)
• Vapor Pressure: 3.51E-05mmHg at 25°C
• Refractive Index: 1.4230 (estimate)
• Storage Temp.: Store at RT
• Solubility: H2O: >10 mg/mL
• PKA: 2.34±0.21(Predicted)
• CAS DataBase Reference: (2S,4R)-4-METHYLGLUTAMIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4R)-4-METHYLGLUTAMIC ACID(31137-74-3)
• EPA Substance Registry System: (2S,4R)-4-METHYLGLUTAMIC ACID(31137-74-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 31137-74-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C6H11NO4/c1-3(5(8)9)2-4(7)6(10)11/h3-4H,2,7H2,1H3,(H,8,9)(H,10,11)/p-1/t3-,4+/m1/s1

Upstream product

• 80-62-6 methacrylic acid methyl ester 
• 171288-20-3 N-boc-(2S,4R)-4-methylpyroglutamic acid 
• 4469-60-7 dimethyl 2,2-dimethoxypentanedioate 
• 1116-76-3 Tri-n-octylamine 
• 171288-21-4 (2S,4R)-N-t-butoxycarbonyl-4-methyl glutamic acid 
• 7148-24-5 diethyl (4-nitrobenzoyl)-L-glutamate 
• 260546-00-7 (-) dimethyl (R)-2,2-dimethoxy-4-methylglutarate 
• 260545-99-1 (R)-2,2-Dimethoxy-4-methyl-pentanedioic acid 1-methyl ester 
• 260545-97-9 (R,S)-dimethyl 2,2-dimethoxy-4-methylglutarate 
• 261159-32-4 dimethyl (R)-4-methyl-2-oxoglutarate 
• 328-50-7 α-ketoglutaric acid 
• 553679-43-9 (2S,4R)-4-Methyl-5-oxo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 7149-65-7 ethyl (S)-pyroglutamate 
• 98-79-3 L-Pyroglutamic acid 

Downstream Products

• 42453-21-4 4-Amino-2-methylbutyric acid 

Relevant articles and documents

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.

Enzymatic Synthesis of 4-Methyl- and 4-Ethyl-L-glutamic Acids

This paper reports the activity of glutamic oxalacetic aminotransferase (GOT) from pig heart and bacteria for racemic 4-hydroxy-, 4-methyl-, and 4-ethyl-2-ketoglutaric acids.These compounds are good substrates for GOT with Vmax values of, respectively, 70, 90, and 130 percent relative to the natural substrate, 2-ketoglutaric acid.GOT displays high enantioselectivity toward 4-methyl-2-ketoglutaric acid and 4-ethyl-2-ketoglutaric acid; the synthesis of both diastereoisomers of the corresponding 4-substituted L-glutamic acids is thus possible.

The first example of asymmetric Michael reaction catalyzed by chiral alkali metal alkoxides

Some chiral sodium alkoxides can be used as catalysts in the asymmetric Michael reaction as exemplified by the 1,4-addition of an achiral NiII complex of the Schiff base derived from glycine and N-(2-pyridylcarbonyl)-o-aminobenzophenone (1) to

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.

Chemoenzymatic synthesis of a series of 4-substituted glutamate analogues and pharmacological characterization at human glutamate transporters subtypes 1-3

A series of nine L-2,4-s;yrc-4-alkylglutamic acid analogues (1a-i) were synthesized in high yield and high enantiomeric excess (>99% ee) from their corresponding 4-substituted ketoglutaric acids (2a-i), using the enzyme aspartate aminotransferase (AAT) from pig heart or E. coli. The synthesized compounds were evaluated as potential ligands for the glutamate transporters EAAT1, EAAT2, and EAAT3 (excitatory amino acid transporter, subtypes 1-3) in the FLIPR membrane potential (FMP) assay. We found a distinct change in the pharmacological profile when the 4-methyl group (compound 1a, an EAAT1 substrate and EAAT2,3 inhibitor) was extended to a 4-ethyl group, compound 1b, as this analogue is an inhibitor at all three subtypes, EAAT1-3. Furthermore, we conclude that both large and bulky hydrophobic substituents in the 4-position of L-2,4-syn Glu are allowed by all three glutamate transporter subtypes EAAT1-3 while maintaining inhibitory activity.

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).

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.