Biocatalytic preparation of (R)-(-)-4-(phenylthio)-2-butanol and (R)-(-)-4-(Phenylsulfonyl)-2-butanol by the sequential use of Pichia farinosa and Rhodococcus rhodochrous

Takeshi Sugai, Yoshikazu Ohtsuka, Hiromichi Ohta

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Abstract

Preparation of (R)-4-(phenylthio)-2-butanol and (R)-4-(phenylsulfonyl)-2-butanol has been established based on the sequential use of two biocatalysts. A Pichia farinosa IAM 4682 mediated reduction of 4-(phenylthio)-2-butanone afforded (R)-4-(phenylthio)-2-butanol (91%e.e.) in 90% yield. Contaminating (S)-enantiomer in the resulting product was selectively oxidized by Rhodococcus rhodochrous IFO15564 to leave pure (R)-enantiomer in 87% yield. From this product, highly enantiomerically pure (R)-4-(phenylsulfonyl)-2-butanol was obtained by hydrogen peroxide oxidation.

Original languageEnglish
Pages (from-to)233-234
Number of pages2
JournalChemistry Letters
Issue number3
Publication statusPublished - 1996

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Enantiomers
Hydrogen Peroxide
Oxidation
2-butanol
Enzymes
methylethyl ketone

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "Biocatalytic preparation of (R)-(-)-4-(phenylthio)-2-butanol and (R)-(-)-4-(Phenylsulfonyl)-2-butanol by the sequential use of Pichia farinosa and Rhodococcus rhodochrous",
abstract = "Preparation of (R)-4-(phenylthio)-2-butanol and (R)-4-(phenylsulfonyl)-2-butanol has been established based on the sequential use of two biocatalysts. A Pichia farinosa IAM 4682 mediated reduction of 4-(phenylthio)-2-butanone afforded (R)-4-(phenylthio)-2-butanol (91{\%}e.e.) in 90{\%} yield. Contaminating (S)-enantiomer in the resulting product was selectively oxidized by Rhodococcus rhodochrous IFO15564 to leave pure (R)-enantiomer in 87{\%} yield. From this product, highly enantiomerically pure (R)-4-(phenylsulfonyl)-2-butanol was obtained by hydrogen peroxide oxidation.",
author = "Takeshi Sugai and Yoshikazu Ohtsuka and Hiromichi Ohta",
year = "1996",
language = "English",
pages = "233--234",
journal = "Chemistry Letters",
issn = "0366-7022",
publisher = "Chemical Society of Japan",
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T1 - Biocatalytic preparation of (R)-(-)-4-(phenylthio)-2-butanol and (R)-(-)-4-(Phenylsulfonyl)-2-butanol by the sequential use of Pichia farinosa and Rhodococcus rhodochrous

AU - Sugai, Takeshi

AU - Ohtsuka, Yoshikazu

AU - Ohta, Hiromichi

PY - 1996

Y1 - 1996

N2 - Preparation of (R)-4-(phenylthio)-2-butanol and (R)-4-(phenylsulfonyl)-2-butanol has been established based on the sequential use of two biocatalysts. A Pichia farinosa IAM 4682 mediated reduction of 4-(phenylthio)-2-butanone afforded (R)-4-(phenylthio)-2-butanol (91%e.e.) in 90% yield. Contaminating (S)-enantiomer in the resulting product was selectively oxidized by Rhodococcus rhodochrous IFO15564 to leave pure (R)-enantiomer in 87% yield. From this product, highly enantiomerically pure (R)-4-(phenylsulfonyl)-2-butanol was obtained by hydrogen peroxide oxidation.

AB - Preparation of (R)-4-(phenylthio)-2-butanol and (R)-4-(phenylsulfonyl)-2-butanol has been established based on the sequential use of two biocatalysts. A Pichia farinosa IAM 4682 mediated reduction of 4-(phenylthio)-2-butanone afforded (R)-4-(phenylthio)-2-butanol (91%e.e.) in 90% yield. Contaminating (S)-enantiomer in the resulting product was selectively oxidized by Rhodococcus rhodochrous IFO15564 to leave pure (R)-enantiomer in 87% yield. From this product, highly enantiomerically pure (R)-4-(phenylsulfonyl)-2-butanol was obtained by hydrogen peroxide oxidation.

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JO - Chemistry Letters

JF - Chemistry Letters

SN - 0366-7022

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