97550-61-3

Usage

Uses

Used in Pharmaceutical Industry:
(2R,3R)-3-Methylglutamic acid is used as a chiral building block for the development of new pharmaceuticals, leveraging its unique stereochemistry to create enantiomerically pure compounds with specific biological activities.
Used in Biomarker Research:
In the field of medical research, (2R,3R)-3-Methylglutamic acid serves as a potential biomarker for colorectal cancer, aiding in the early detection and monitoring of the disease.
Used in Asymmetric Synthesis:
(2R,3R)-3-Methylglutamic acid is utilized as a chiral auxiliary or catalyst in asymmetric synthesis, enabling the production of enantiomerically enriched compounds for various applications, including pharmaceuticals and agrochemicals.
Used in Microbiology Research:
As a component of bacterial peptidoglycan, (2R,3R)-3-Methylglutamic acid is used in microbiology to study bacterial cell wall structure and function, as well as its role in bacterial metabolism and pathogenesis.

Upstream product

• 291763-98-9 (2R,3R)-3-methylpyroglutamic acid 
• 113647-41-9 (2R,3R)-tert-butyl trans-3-methyl-5-oxopyrroldine-2-carboxylate 
• 76318-75-7 erythro-β-methylglutamic acid 
• 129397-19-9 (2R,3S)-2-Dibenzylamino-3-methyl-pentanedioic acid di-tert-butyl ester 
• 129397-27-9 (2S,3R)-2-Dibenzylamino-3-methyl-pentanedioic acid 

Downstream Products

• 917026-03-0 (2S,3R)-3-methyl-N-phthaloylglutamic acid anhydride 

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).

Development of catalytic asymmetric 1,4-addition and [3 + 2] cycloaddition reactions using chiral calcium complexes

Catalytic asymmetric 1,4-addition and [3 + 2] cycloaddition reactions using chiral calcium species prepared from calcium isopropoxide and chiral bisoxazoline ligands have been developed. Glycine Schiff bases reacted with acrylic esters to afford 1,4-addition products, glutamic acid derivatives, in high yields with high enantioselectivities. During the investigation of the 1,4-addition reactions, we unexpectedly found that a [3 + 2] cycloaddition occurred in the reactions with crotonate derivatives, affording substituted pyrrolidine derivatives in high yields with high enantioselectivities. On the basis of this finding, we investigated asymmetric [3 + 2] cycloadditions, and it was revealed that several kinds of optically active substituted pyrrolidine derivatives containing contiguous stereogenic tertiary and quaternary carbon centers were obtained with high diastereo- and enantioselectivities. In addition, optically active pyrrolidine cores of hepatitis C virus RNA-dependent polymerase inhibitors and potential effective antiviral agents have been synthesized using this [3 + 2] cycloaddition reaction. NMR spectroscopic analysis and observation of nonamplification of enantioselectivity in nonlinear effect experiments suggested that a monomeric calcium species with an anionic ligand was formed as an active catalyst. A stepwise mechanism of the [3 + 2] cycloaddition, consisting of 1,4-addition and successive intramolecular Mannich-type reaction was suggested. Furthermore, modification of the Schiff base structure resulted in a modification of the reaction course from a [3 + 2] cycloaddition to a 1,4-addition, affording 3-substituted glutamic acid derivatives with high diasterero- and enantioselectivities.

Calcium-catalyzed diastereo- and enantioselective 1,4-addition of glycine derivatives to α,β-unsaturated esters

The first highly diastereo- and enantioselective catalytic asymmetric 1,4-addition reactions of a glycine Schiff base to β-substituted α, β-unsaturated esters have been developed. The reaction pathway was successfully controlled, and the desired 1,4-addition products were exclusively obtained with high enantioselectivities. The product obtained was converted to a 3-substituted glutamic acid derivative by acid hydrolysis.

Efficient asymmetric synthesis of novel 4-substituted and configurationally stable analogues of thalidomide

The preparation of new thalidomide derivatives 4-methyl-(3S,4R)-3a and 4-phenyl-(3S,4S)-3b starting from pyroglutamic acids (2R,3R)-7a and (2R,3S)-7b, possessing an inappropriate stereochemistry, was successfully realized due to stereochemically complete epimerization at the α-stereogenic center upon formation of the corresponding N-phthaloyl anhydrides 9a,b. The demonstrated conformational stability of these new thalidomide derivatives provides solid experimental evidence for practical feasibility of the approach described here to overcome the inherent problem of configurational instability of thalidomide by introducing an alkyl or aryl group in the C4 position.

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.

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.

threo-Selective Michael Addition of N,N-Dibenzylglycinate and Alaninate Enolates to α,β-Unsaturated Esters. A Concise and Stereoselective Synthesis of (+/-)-CCG-II

Lithium enolates of N,N-dibenzylglycinate and alaninate added to β-substituted α,β-unsaturated esters, and threo-adducts were obtained in high stereoselectivities.The reaction was employed in a concise and stereoselective synthesis of (+/-)-CCG-II.