111492-38-7Relevant academic research and scientific papers
Purification and Properties of Aldehyde Reductases from Yeasts That Convert Ethyl 2-Acetamido-3-oxobutyrate to Optically Active Ethyl 2-Acetamido-3-hydroxybutyrate
Kato, Nobuo,Fujie, Masayoshi,Hasegawa, Masayasu,Shimao, Masayuki,Kita, Keiko,Yanase, Hideshi
, p. 303 - 307 (2007/10/02)
Yeasts were screened for strains that converted ethyl 2-acetamido-3-oxobutyrate (AAOB) to optically active ethyl 2-acetamido-3-hydroxybutyrate (AAHB).Sporobolomyces sp.AKU4430 was found to accumulate the D-threo isomer of AAHB by a whole-cell reaction.Candida albicans AKU4596 accumulated mainly the D-threo and L-threo isomers.The enzymes that reduced AAOB were purified from these two yeasts, and characterized.To judge from their substrate specifity, inhibition pattern, molecular structure, and reaction mechanisms, the enzymes were of the NADPH-dependent aldo-keto reductase family (probably aldehyde reductase, EC 1.1.1.2).The enzyme of Sporobolomyces sp. reduced AAOB more strongly than that of C. albicans.The stereoselectivity of the enzymes was low; three isomers of AAHB (L-threo, L-allo, and D-threo) were produced by each purified enzyme.The selective accumulation of an isomer(s) of AAHB by reaction in yeast cells probably occurred because of differences in isomer degradation.
ASYMMETRIC SYNTHESIS. PRACTICAL PRODUCTION OF D AND L THREONINE. DYNAMIC KINETIC RESOLUTION IN RHODIUM AND RUTHENIUM CATALYZED HYDROGENATION OF 2-ACYLAMINO-3-OXOBUTYRATES.
Genet, J.P.,Pinel, C.,Mallart, S.,Juge, S.,Thorimbert, S.,Laffitte, J.A.
, p. 555 - 567 (2007/10/02)
Enantioselective syntheses of D and L threonine are described.Racemic methyl and ethyl 2-acylamino-3-oxobutyrate 1 were synthesized from the corresponding acetoacetates 6 and then hydrogenated stereoselectively via dynamic kinetic resolution with various chiral P * P Rh(I) 8 and Ru(II) 10 catalysts to give syn optically active alcohols which could be converted by hydrolysis and treatment with propylene oxide into threonine.The best results were obtained using (-) CHIRAPHOS Ru and (+) BINAP Ru as catalysts, in the hydrogenation step leading respectively to D threonine (ee : 99percent) and L threonine (ee : 94percent) in 26-34percent overall yields.
