Biotransformation of β-ketosulfides to produce chiral β-hydroxysulfoxides

H. L. Holland, F. M. Brown, F. Barrett, J. French, D. V. Johnson

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

The biotransformations of a series of substituted phenylthio-2-propanone and benzylthio-2-propanone were carried out using Helminthosporium sp. NRRL 4671, Mortierella isabellina ATCC 42613, or Rhodococcus erythropolis IGTS8. Several products gave microbial oxidation of sulfide to sulfoxide and reduction of carbonyl to secondary alcohol, producing β-hydroxysulfoxides in medium to high enantiomeric and diastereomeric purities. Fungal biotransformations using Helminthosporium sp. and M. isabellina resulted in the opposite sulfoxide configurations of various β-hydroxysulfoxide products.

Original languageEnglish (US)
Pages (from-to)292-301
Number of pages10
JournalJournal of Industrial Microbiology and Biotechnology
Volume30
Issue number5
DOIs
StatePublished - May 1 2003
Externally publishedYes

Keywords

  • Biocatalysis
  • Biotransformation
  • Carbonyl reduction
  • Helminthosporium sp. NRRL 4671
  • Mortierella isabellina ATCC 42613
  • Rhodococcus erythropolis IGTS8
  • Sulfoxidation

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