Preparation of Both Enantiomers of Ethyl 3-Hydroxybutanoate by Microbial Methods

Takeshi Sugai, Mitsuru Fujita, Kenji Mori

Research output: Contribution to journalArticle

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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 languageEnglish
Pages (from-to)1315-1321
Number of pages7
JournalNippon Kagaku Kaishi
Volume1983
Issue number9
DOIs
Publication statusPublished - 1983
Externally publishedYes

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Enantiomers
Yeast
Biological Products
Esters
Temperature

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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 journalArticle

Sugai, Takeshi ; Fujita, Mitsuru ; Mori, Kenji. / Preparation of Both Enantiomers of Ethyl 3-Hydroxybutanoate by Microbial Methods. In: Nippon Kagaku Kaishi. 1983 ; Vol. 1983, No. 9. pp. 1315-1321.
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