Screening, substrate specificity and stereoselectivity of yeast strains, which reduce sterically hindered isopropyl ketones

Chihiro Hiraoka, Masaaki Matsuda, Yuya Suzuki, Shigeo Fujieda, Mina Tomita, Ken ichi Fuhshuku, Rika Obata, Shigeru Nishiyama, Takeshi Sugai

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

Towards the synthesis of sterically hindered optically active secondary alcohol 2, yeast strains (Candida floricola IAM 13115 and Trichosporon cutaneum IAM 12206) with si-face hydride attack on isopropyl phenylsulfonylmethyl ketone 1 were developed by screening. Strains with complementary re-facial selectivity (Pichia angusta IAM 12895 and Pichia minuta IAM 12215) were also found. Based on the substrate specificity studies of these four strains, microbial reduction was applied to the synthesis of (3S,5S)-2,6-dimethyl-3,5-heptanediol 12a.

Original languageEnglish
Pages (from-to)3358-3367
Number of pages10
JournalTetrahedron Asymmetry
Volume17
Issue number24
DOIs
Publication statusPublished - 2006 Dec 27

Fingerprint

Stereoselectivity
Pichia
yeast
Substrate Specificity
Ketones
ketones
Yeast
Screening
screening
Yeasts
Trichosporon
Candida
Substrates
synthesis
Hydrides
attack
hydrides
alcohols
Alcohols
selectivity

ASJC Scopus subject areas

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

Cite this

Screening, substrate specificity and stereoselectivity of yeast strains, which reduce sterically hindered isopropyl ketones. / Hiraoka, Chihiro; Matsuda, Masaaki; Suzuki, Yuya; Fujieda, Shigeo; Tomita, Mina; Fuhshuku, Ken ichi; Obata, Rika; Nishiyama, Shigeru; Sugai, Takeshi.

In: Tetrahedron Asymmetry, Vol. 17, No. 24, 27.12.2006, p. 3358-3367.

Research output: Contribution to journalArticle

Hiraoka, C, Matsuda, M, Suzuki, Y, Fujieda, S, Tomita, M, Fuhshuku, KI, Obata, R, Nishiyama, S & Sugai, T 2006, 'Screening, substrate specificity and stereoselectivity of yeast strains, which reduce sterically hindered isopropyl ketones', Tetrahedron Asymmetry, vol. 17, no. 24, pp. 3358-3367. https://doi.org/10.1016/j.tetasy.2006.12.013
Hiraoka, Chihiro ; Matsuda, Masaaki ; Suzuki, Yuya ; Fujieda, Shigeo ; Tomita, Mina ; Fuhshuku, Ken ichi ; Obata, Rika ; Nishiyama, Shigeru ; Sugai, Takeshi. / Screening, substrate specificity and stereoselectivity of yeast strains, which reduce sterically hindered isopropyl ketones. In: Tetrahedron Asymmetry. 2006 ; Vol. 17, No. 24. pp. 3358-3367.
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