33511-69-2

Usage

Uses

Used in Biochemistry and Organic Chemistry Research:
(2S,3R)-3-Methylglutamic acid is used as a research tool for studying protein structure and function, providing insights into the mechanisms of enzyme catalysis and protein folding.
Used in Pharmaceutical Synthesis:
(2S,3R)-3-Methylglutamic acid is used as a building block in the synthesis of various pharmaceuticals and other bioactive molecules, contributing to the development of new drugs and therapeutic agents.
Used in Neurological Disorder Treatment:
(2S,3R)-3-Methylglutamic acid has potential therapeutic applications for treating neurological disorders and neurodegenerative diseases, offering a promising avenue for the development of novel treatments and interventions.

Upstream product

• 129397-19-9 (2R,3S)-2-Dibenzylamino-3-methyl-pentanedioic acid di-tert-butyl ester 
• 83855-20-3 Neopeptin A 
• 83855-21-4 Neopeptin B 
• 89838-29-9 Neopeptin C 
• 160006-15-5 1-isopropyl 5-methyl (2S,3R)-3-methyl-N-(trifluoroacetyl)glutamate 
• 160006-13-3 1-isopropyl (2S,3S)-3-methyl N-trifluoroacetylaspartoyl chloride 
• 116063-91-3 2,2,2-Trifluoro-N-((3S,4S)-4-methyl-2,5-dioxo-tetrahydro-furan-3-yl)-acetamide 
• 6061-13-8 (2S,3S)-3-methylaspartic acid 
• 531539-43-2 (2S,3R,4S)-3-methyl-2-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)-5-oxo-4-phenylselenenyl-pyrrolidine-1-carboxylic acid benzyl ester 
• 461639-00-9 (2S)-2-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-5-oxo-pyrrolidine-1-carboxylic acid benzyl ester 
• 531539-18-1 (2S)-1-benzyloxycarbonyl-5-oxo-pyrrolidine-2-carboxylic acid 2-(3-methyl-oxetan-3-yl-methyl) ester 
• 531539-44-3 (2S)-3-methyl-2-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)-5-oxo-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester 
• 531539-24-9 (2S,3S)-2-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-5-oxo-3-methyl-pyrrolidine-1-carboxylic acid benzyl ester 
• 531539-23-8 (2S)-2-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-5-oxo-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

Optically pure 3 - methyl glutamic acid derivatives preparation method

The invention discloses a preparation method of an optically pure 3-methyl glutamic acid derivative. The optically pure 3-methyl glutamic acid derivative is obtained through asymmetric Michael addition and a hydrolysis reaction of camphor-derived tricycloiminolactone and crotonate. The preparation method of the optically pure 3-methyl glutamic acid derivative is high in stereoselectivity and yield of an obtained product, low in production cost, and high in product purity and enantiomeric excess.

Temperature-Dependent Enantio- and Diastereodivergent Synthesis of Amino Acids with One or Multiple Chiral Centers

A general and facile methodology for temperature-dependent enantiodivergent and diastereodivergent synthesis of amino acids with one or multiple chiral centers was developed. Camphor-based tricyclic iminolactones attack electrophiles from the endo face at low temperature (-78 to -40 °C) and from the exo face at high temperature (-10 to 25 °C).

Isolation and structural elucidation of callipeltins J-M: antifungal peptides from the marine sponge Latrunculia sp.

Continued investigation of the polar extracts of the marine sponge Latrunculia sp. has resulted in the discovery of callipeltins J-M. The new structures were determined by interpretation of their NMR and MS data. The stereochemistry of the unusual 3-methy

Stereospecific enzymatic transformation of α-ketoglutarate to (2S,3R)-3-methyl glutamate during acidic lipopeptide biosynthesis

The acidic lipopeptides, including the calcium-dependent antibiotics (CDA), daptomycin, and A54145, are important macrocyclic peptide natural products produced by Streptomyces species. All three compounds contain a 3-methyl glutamate (3-MeGlu) as the penultimate C-terminal residue, which is important for bioactivity. Here, biochemical in vitro reconstitution of the 3-MeGlu biosynthetic pathway is presented, using exclusively enzymes from the CDA producer Streptomyces coelicolor. It is shown that the predicted 3-MeGlu methyltransferase GlmT and its homologues Dptl from the daptomycin producer Streptomyces roseosporus and Lptl from the A54145 producer Streptomyces fradiae do not methylate free glutamic acid, PCP-bound glutamate, or Glu-containing CDA in vitro. Instead, GlmT, Dptl, and Lptl are S-adenosyl methionine (SAM)-dependent α-ketoglutarate methyltransferases that catalyze the stereospecific methylation of α-ketoglutarate (αKG) leading to (3R)-3-methyl-2-oxoglutarate. Subsequent enzyme screening identified the branched chain amino acid transaminase IIvE (SCO5523) as an efficient catalyst for the transformation of (3R)-3-methyl-2-oxoglutarate into (2S,3R)-3-MeGlu. Comparison of reversed-phase HPLC retention time of dabsylated 3-MeGlu generated by the coupled enzymatic reaction with dabsylated synthetic standards confirmed complete stereocontrol during enzymatic catalysis. This stereospecific two-step conversion of αKG to (2S,3R)-3-MeGlu completes our understanding of the biosynthesis and incorporation of β-methylated amino acids into the nonribosomal lipopeptides. Finally, understanding this pathway may provide new possibilities for the production of modified peptides in engineered microbes.

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.

Polytheonamides A and B, highly cytotoxic, linear polypeptides with unprecedented structural features, from the marine sponge, Theonella swinhoei

Polytheonamides A and B are highly cytotoxic polypeptides with 48 amino acid residues isolated from the marine sponge, Theonella swinhoei. The structure of polytheonamide B was determined by spectral and chemical methods, especially extensive 2D NMR experiments, which resulted in the unprecedented polypeptide structure; the N-terminal glycine blocked with a 5,5-dimethyl-2-oxo-hexanoyl group, the presence of eight tert-leucine, three β-hydroxyvaline, six γ-N-methylasparagine, two γ-N-methyl-β-hydroxyasparagine, and β,β-dimethymethionine sulfoxide residues. More significantly, it has the sequence of alternating D-and L-amino acids. Polytheonamide A is an epimer of polytheonamide B differing only in the stereochemistry of the sulfoxide of the 44th residue.

Glutamate transporter blockers: Enantiomerically pure (2S,3S)- and (2S,3R)-3-methyl glutamic acids

A short four-step synthesis of (2S,3R)- and (2S,3S)-3-methyl glutamic acids is reported; the (2S,3R) isomer presented a significant inhibitory effect on glutamate transport.

A stereoselective synthesis of 3-substituted (S)-pyroglutamic and glutamic acids via OBO ester derivatives

(S)-Pyroglutamic acid is transformed to the Cbz-protected 4-methyl-2,6,7-trioxabicyclo[2.2.2] octane (OBO) ester. This ortho ester functionality is employed as a bulky steering group for stereoselective introduction of alkyl and aryl groups via 1,4-cuprate addition to 3,4-unsaturated pyroglutamates. After deprotection and ringopening, 3-substituted glutamic acids are obtained.

Synthesis of (2S,3R)- and (2S,3S)-3-Methylglutamic Acid

Arndt-Eistert homologation of suitably protected (2S,3S)-3-methylaspartic acid occurs with retention of configuration at C-3 to give, ultimately, (2S,3R)-3-methylglutamic acid. (2S,3R)-3-Methylglutamic acid was also prepared in good yield via the conjugate addition of the lithiated anion of the bis-lactim ether of cyclo-(R-Val-Gly) to methyl (E)-butenoate.The analogous reaction performed using isopentyl (Z)-butenoate ultimately gave (2S,3S)-3-methylglutamic acid.Both conjugate additions occured with high diastereoselectivity.

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.