50732-06-4

Usage

InChI:InChI=1/C13H17NO3S/c1-17-13(16)11(8-9-18-2)14-12(15)10-6-4-3-5-7-10/h3-7,11H,8-9H2,1-2H3,(H,14,15)/t11-/m0/s1

Upstream product

• 67-56-1 methanol 
• 51127-20-9 4-(2-methylsulfanyl-ethyl)-2-phenyl-4H-oxazol-5-one 
• 2491-18-1 (S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride 

Downstream Products

• 1626437-63-5 1-benzoyl-5-(2-(methylthio)ethyl)pyrrolidine-2,4-dione 
• 10290-61-6 (S)-N-benzoylmethionine 
• 1303536-70-0 (S)-N-[1-hydroxy-4-(methylthio)butan-2-yl]benzamide 
• 101650-13-9 (S)-Bz-homoAla(I)-OMe 
• 82933-21-9 N-benzoyl-L-aspartic acid α-methyl ester 
• 115527-63-4 Bz-Met(sulfone)-OH 
• 56762-94-8 Bz-Met(sulfone)-OMe 
• 3054-52-2 N-benzoyl L-methionine sulphoxide 
• 56782-76-4 Bz-Met(sulfoxide)-OMe 
• 115527-64-5 BzNHCH(CH₂CH₂SO₂H)COOMe 

Relevant academic research and scientific papers

Dynamic kinetic resolution: Synthesis of optically active α-amino acid derivatives

Candida antarctica lipase B (Novozyme) is an effective catalyst for the dynamic kinetic resolution of racemic 2-benzyl-4-substituted-5(4H)- oxazolones, in the presence of an alcohol, yielding optically active N- benzoyl amino acid esters. The reaction has been optimised with respect to the solvent and the effect of a catalytic amount of organic base is investigated. (C) 2000 Elsevier Science Ltd.

Enzymatic Asymmetric Synthesis of α-Amino Acids. Enantioselective Cleavage of 4-Substituted Oxazolin-5-ones and Thiazolin-5-ones

A general enzymatic asymmetric synthesis of L-α-amino acids has been developed.This method entails the use of the Pseudomonas cepacia lipase (P-30) to catalyze the enantioselective methanolysis of a variety of 4-substituted 2-phenyloxazolin-5-one derivatives in a nonpolar organic solvent to furnish optically active N-benzoyl-L-α-amino acid methyl esters (ee = 66-98 percent), which in turn is subjected to a protease-catalyzed kinetic resolution yielding enantiomerically pure N-benzoyl-L-α-amino acids.This synergistic coupling of two enzymes allows the ready preparation of L-α-amino acids of high enantiopurity in yields greater than 50 percent, an inherent advantage over conventional resolution procedures.Two proteases were found to catalyze the enantioselective hydrolysis of a variety of 4-substituted 2-phenylthiazolin-5-one derivatives to give N-(thiobenzoyl)-L-α-amino acids of high optical purity.

L-METHIONINE OXIDATION: NOVEL AND UNANTICIPATED TRANSFORMATIONS WITH 4-tBUTYL IODOXYBENZENE

4-tButyl iodoxybenzene transforms Bz-Met-OMe to products arising from, S oxidation and C-H insertion followed by degradation.Z-Met(sulfoxide)-OMe is very effective in bringing about ester hydrolysis via intramolecular attack.The S oxidation to sulfoxides and then to sulfones can be monitored and controlled, proceeds with chiral retention, affects neither the peptide bond nor the protecting groups and has been further illustrated with,Z-Gly-Met-OMe, Z-Met-OMe and Z-S(benzyl)-Cys-OMe.