TY - JOUR
T1 - Preparation of Both Enantiomers of Ethyl 3-Hydroxybutanoate by Microbial Methods
AU - Sugai, Takeshi
AU - Fujita, Mitsuru
AU - Mori, Kenji
PY - 1983
Y1 - 1983
N2 - Both enantiomers of ethyl 3-hydroxybutanoate which are useful chiral starting materials for the synthesis of natural products containing CH3CH(OH)CH2R group have been prepared in a 3~18 g scale by microbial methods. Ethyl acetoacetate was enantio-selectively reduced to the 5-enantiomer by baker's yeast (in 83~90% e. e.) and by high temperature yeast (in 96% e. e., see Table 3). Asymmetric reductions by several brewer's yeasts (in 43~92% e. e.) and by commercially available HLADH, YADH (in 100% e. e.) gave also the 5-enantiomer. The R-enantiomer was prepared from poly (3-hydroxybutanoate) (PHB) produced by Zoogloea rami-gera, in 100% e. e. Their optical purities were determined by the HPLC analyses of the corresponding MTPA esters.
AB - Both enantiomers of ethyl 3-hydroxybutanoate which are useful chiral starting materials for the synthesis of natural products containing CH3CH(OH)CH2R group have been prepared in a 3~18 g scale by microbial methods. Ethyl acetoacetate was enantio-selectively reduced to the 5-enantiomer by baker's yeast (in 83~90% e. e.) and by high temperature yeast (in 96% e. e., see Table 3). Asymmetric reductions by several brewer's yeasts (in 43~92% e. e.) and by commercially available HLADH, YADH (in 100% e. e.) gave also the 5-enantiomer. The R-enantiomer was prepared from poly (3-hydroxybutanoate) (PHB) produced by Zoogloea rami-gera, in 100% e. e. Their optical purities were determined by the HPLC analyses of the corresponding MTPA esters.
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U2 - 10.1246/nikkashi.1983.1315
DO - 10.1246/nikkashi.1983.1315
M3 - Article
AN - SCOPUS:84986687672
VL - 1983
SP - 1315
EP - 1321
JO - Nippon Kagaku Kaishi / Chemical Society of Japan - Chemistry and Industrial Chemistry Journal
JF - Nippon Kagaku Kaishi / Chemical Society of Japan - Chemistry and Industrial Chemistry Journal
SN - 0369-4577
IS - 9
ER -