Abstract
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.
| Original language | English |
|---|---|
| Pages (from-to) | 1315-1321 |
| Number of pages | 7 |
| Journal | Nippon Kagaku Kaishi |
| Volume | 1983 |
| Issue number | 9 |
| DOIs | |
| Publication status | Published - 1983 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Chemistry(all)
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Preparation of Both Enantiomers of Ethyl 3-Hydroxybutanoate by Microbial Methods. / Sugai, Takeshi; Fujita, Mitsuru; Mori, Kenji.
In: Nippon Kagaku Kaishi, Vol. 1983, No. 9, 1983, p. 1315-1321.Research output: Contribution to journal › Article
}
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.
UR - http://www.scopus.com/inward/record.url?scp=84986687672&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84986687672&partnerID=8YFLogxK
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 -