71-90-9

Usage

Uses

Used in Chemical Synthesis Studies:
DL-2-METHYLGLUTAMIC ACID is used as a key intermediate for the synthesis of various pharmaceuticals and other chemical compounds. Its unique structure allows it to be a versatile building block in the development of new molecules with potential applications in the medical and pharmaceutical industries.
Used in Pharmaceutical Industry:
DL-2-METHYLGLUTAMIC ACID is used as a starting material for the production of certain drugs, particularly those targeting neurological disorders. Its ability to be modified and incorporated into more complex molecules makes it a valuable asset in the design and synthesis of novel therapeutic agents.
Used in Research and Development:
DL-2-METHYLGLUTAMIC ACID is utilized as a research compound in the study of its properties and potential applications. This includes investigations into its interactions with other molecules, its stability under various conditions, and its potential use in the development of new technologies and products.

InChI:InChI=1/C6H11NO4/c1-6(7,5(10)11)3-2-4(8)9/h2-3,7H2,1H3,(H,8,9)(H,10,11)/p-1/t6-/m0/s1

Upstream product

• 86240-21-3 5-cyano-5-methyl-2-pyrrolidone 
• 43189-49-7 racemic 3-(4-methyl-2,5-dioxoimidazolidin-4-yl)propionic acid 
• 123187-58-6 2-acetyl-4-cyano-2-methyl-butyric acid ethyl ester 
• 143-33-9 sodium cyanide 
• 123-76-2 levulinic acid 
• 73838-85-4 α-methyl-(E)-3,4-dehydroglutamic acid 
• 202271-71-4 Cbz-DL-α-methylglutamic acid 
• 73838-90-1 Dimethyl (E)-2-(benzylideneamino)-2-methylpent-3-ene-2,5-dioate 

Downstream Products

• 127027-18-3 2-acetylamino-2-methyl-glutaric acid 
• 4493-08-7 (R)-α-Methylglutamic acid 
• 6208-95-3 (2S)-alpha-Methylglutamate 
• 95755-22-9 N-<4-<<(2,4-diamino-6-pteridinyl)methyl>methylamino>benzoyl>-2-methyl-glutamic acid 
• 202271-71-4 Cbz-DL-α-methylglutamic acid 
• 56009-38-2 dimethyl 2-amino-2-methylpentanedioate 

Relevant academic research and scientific papers

Microbial enantioselective removal of the N-benzyloxycarbonyl amino protecting group

In order to deprotect N-carbobenzoxy-l-aminoacids (Cbz-AA) and related compounds, a series of microorganisms was selected from soil by enrichment cultures with Cbz-l-Glu as sole nitrogen source. A lyophilized whole-cell preparation of two Arthrobacter sp. strains grown on Cbz-Glu or Cbz-Gly exhibited a high cleavage activity. The conditions of hydrolysis have been optimized and a quantitative enantioselective deprotection of several Cbz-dl-amino acids was obtained, as well as the deprotection of N-carbamoylester derivatives of several synthetic amino compounds. The preparation of Cbz-d-allylglycine and l-allylglycine in high yield and high optical purity is described as an application of this method.

Stereospecific Alkylation of the Schiff Base Ester of Alanine with 2-Substituted-(E)- and -(Z)-vinyl Bromides. An Efficient Synthesis of 2-Methyl-(E)-3,4-didehydroglutamic Acid, a Potent Substrate-Induced Irreversible Inhibitor of L-Glutamate-1-decarboxylase.

The nucleophilic vinylic substitution by the enolate of methyl N-benzylidenealanate (1) of (E)- and (Z)-vinylbromides 4 and 5 has been examined as an approach to the synthesis of the E and Z isomers of 2-methyl-3,4-didehydroglutamic acid.Under aprotic conditions, the nucleophilic displacement has been found to proceed stereospecifically with retention of configuration of the double bond to afford in good yield the corresponding (E)- and (Z)-substituted products.The configuration of the substitution products has been assigned from the analysis of their 1H NMR spectra on the basis of the value of the coupling constant of the vicinal vinyl ic protons.Subsequent removal of the protecting groups from the substitution products 6 in the E series gives the corresponding 2-methyl-(E)-3,4-didehydroglutamic acid derivatives 2 in good yield.The Z isomers 3 prove to be very unstable and have not been isolated.