Control of enantioselectivity in the baker's yeast asymmetric reduction of γ-chloro β-diketones to γ-chloro (S)-β-hydroxy ketones

Jing Nan Cui, Tadashi Ema, Takashi Sakai, Masanori Utaka

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

1-Chloro-2,4-alkanediones 1a-f prepared in one step were reduced using baker's yeast to afford 1-chloro-2-hydroxy-4-alkanones 2a-f regioselectively in S 29% to R 58% ee. Use of a small amount of organic solvents to dissolve the substrate enhanced the enantiomeric excess in favor of the S configuration. The function of the organic solvents was studied with reducing enzymes isolated from baker's yeast. Some polar solvents selectively inhibited the enzymes, while nonpolar solvents enhanced the concentration of substrate in water. Application of inhibitors with heat-treatment and organic solvents as additives enhanced the enantiomeric excesses of the products to S 66-96% ee.

Original languageEnglish
Pages (from-to)2681-2692
Number of pages12
JournalTetrahedron Asymmetry
Volume9
Issue number15
DOIs
Publication statusPublished - Aug 1998

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Enantioselectivity
yeast
Ketones
ketones
Yeast
Organic solvents
Saccharomyces cerevisiae
Enzymes
Substrates
enzymes
Heat treatment
Water
inhibitors
heat treatment
Hot Temperature
products
configurations
water

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry
  • Materials Chemistry
  • Drug Discovery

Cite this

Control of enantioselectivity in the baker's yeast asymmetric reduction of γ-chloro β-diketones to γ-chloro (S)-β-hydroxy ketones. / Cui, Jing Nan; Ema, Tadashi; Sakai, Takashi; Utaka, Masanori.

In: Tetrahedron Asymmetry, Vol. 9, No. 15, 08.1998, p. 2681-2692.

Research output: Contribution to journalArticle

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