89355-35-1

Upstream product

• 123325-64-4 benzyl 2-methyl-3-oxobutanoate 
• 37526-94-6 Benzyl-3-hydroxy-2-methylbutyrat 
• 5396-89-4 benzyl acetoacetate 
• 37526-94-6 (S)-3-Hydroxy-2-methyl-butyric acid benzyl ester 
• 100-51-6 benzyl alcohol 
• 609-14-3 2-acetylpropanoic acid ethyl ester 
• 89355-33-9 (2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-butyric acid benzyl ester 
• 66767-65-5 Sodium; (2R,3R)-3-hydroxy-2-methyl-butyrate 
• 89355-32-8 (2R,3S)-3-((1,1-dimethylethyl)dimethylsiloxy)-2-methylbutanoic acid benzyl ester 

Downstream Products

• 37526-94-6 benzyl (2S,3R)-2-methyl-3-hydroxybutanoate 
• 37526-94-6 benzyl (2S,3S)-2-methyl-3-hydroxybutanoate 
• 89355-36-2 (2S,3R)-2-Methyl-3-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-butyric acid benzyl ester 
• 89355-36-2 (2R,3R)-2-Methyl-3-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-butyric acid benzyl ester 
• 89355-36-2 (2S,3S)-2-Methyl-3-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-butyric acid benzyl ester 
• 89355-36-2 (2R,3S)-2-Methyl-3-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-butyric acid benzyl ester 
• 89355-37-3 (2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-butyric acid benzyl ester 
• 89355-32-8 (2R,3S)-3-((1,1-dimethylethyl)dimethylsiloxy)-2-methylbutanoic acid benzyl ester 
• 89355-33-9 (2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-butyric acid benzyl ester 

Relevant academic research and scientific papers

Purification and Characterization of Ethyl 2-Methyl-3-oxobutanoate Reductase from Klebsiella pneumoniae IFO3319

An enzyme that catalyzes a reduction of ethyl 2-methyl-3-oxobutanoate (1) to ethyl (2R,3S) 3-hydroxy-2-methylbutanoate was found in Klebsiella pneumoniae IFO 3319 cells. The enzyme was isolated from the cells and purified 250-fold by ammonium sulfate frac

Access to enantiopure α-alkyl-β-hydroxy esters through dynamic kinetic resolutions employing purified/overexpressed alcohol dehydrogenases

α-Alkyl-β-hydroxy esters were obtained via dynamic kinetic resolution (DKR) employing purified or crude E. coli overexpressed alcohol dehydrogenases (ADHs). ADH-A from R. ruber, CPADH from C. parapsilosis and TesADH from T. ethanolicus afforded syn-(2R,3S) derivatives with very high selectivities for sterically not impeded ketones ('small-bulky' substrates), while ADHs from S. yanoikuyae (SyADH) and Ralstonia sp. (RasADH) could also accept bulkier keto esters ('bulky-bulky' substrates). SyADH also provided preferentially syn-(2R,3S) isomers and RasADH showed in some cases good selectivity towards the formation of anti-(2S,3S) derivatives. With anti-Prelog ADHs such as LBADH from L. brevis or LKADH from L. kefir, syn-(2S,3R) alcohols were obtained with high conversions and diastereomeric excess in some cases, especially with LBADH. Furthermore, due to the thermodynamically favoured reduction of these substrates, it was possible to employ just a minimal excess of 2-propanol to obtain the final products with quantitative conversions. Copyright

Stereochemical Control in Microbial Reduction. 9. Diastereoselective Reduction of 2-Alkyl-3-oxobutanoate with Bakers' Yeast

Bakers' yeast reduces esters of 2-alkyl-3-oxobutanoic acid (CH3COCHRCO2R'; R=methyl, ethyl, propyl, propargyl, and allyl) into the corresponding (S)-hydroxy esters with exclusive stereoselectivity, while the configuration at the 2-position of the hydroxy esters is either S (anti) or R (syn) depending on the structure of the alkoxyl group in the carboalkoxyl moeity of the ester.Oftently, the stereoselectivity with respect to the 2-position is not satisfactory.In general, the reduction of t-butyl esters exerts predominancy in the products, whereas that of 1,1-dimethylpropyl esters exerts the syn predominancy.A marked difference between these two esters in diastereoselectivity is dicussed from the view point of plausible conformations of the esters.

Purification and Properties of an Asymmetric Reduction Enzyme of 2-Methyl-3-oxobutyrate in Baker's Yeast

The benzyl 2-methyl-3-hydroxybutyrate dehydrogenase was purified from the cells of Baker's yeast by streptomycin treatment, Sephadex G-50 gel filtration, SP-Sephadex C-5o chromatography, and Toyopearl HW-60F gel filtration.The purified enzyme preparation was homogeneous and the molecular weight was about 31,000 to 32,000.The enzyme was NADPH-dependent and its maximum activity was at pH 7.0 and 45 deg C.It was stable between pH 6 and 9.The Km values at pH 7.0 were 0.42 mM for benzyl 2-methyl-3-oxobutyrate (1) and 4.2 mM for α-methyl β-hydroxy ester .This enzyme reduced only benzyl 2-methyl-3-oxobutyrate (1) but had no effect on other synthetic substrates.

The Use of Microorganisms in Organic Synthesis. I. Microbiological Asymmetric Reduction of 2-Methyl-3-oxobutyrates

The synthesis of optically active α-methyl β-hydroxy esters I by means of microbiological reduction of the corresponding β-keto esters II was carried out.Benzyl 2-methyl-3-oxobutyrate 1 was found to be reduced by a variety of yeasts to the α-methyl β-hydr