Thermostable Enzymes in Organic Synthesis. 2.1 Asymmetric Reduction of Ketones with Alcohol Dehydrogenase from Thermoanaerobium brockii

Ehud Keinan*, Eva K. Hafeli, Kamal K. Seth, Raphael Lamed

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

268 Scopus citations

Abstract

The asymmetric reduction of aliphatic acyclic ketones (C4-C10substrates) is efficiently achieved by using alcohol dehydrogenase from Thermoanaerobium brockii either as a homogeneous, heat-treated, cell-free extract or following immobilization on a solid support. Both methods are superior to the use of whole-cell fermentation. The experimental conditions for working with TBADH were studied and optimized in order to improve reaction rates and the optical purity of the product. An interesting substrate size-induced reversal of stereoselectivity was observed. The smaller substrates (methyl ethyl, methyl isopropyl, or methyl cyclopropyl ketones) are reduced to R alcohols, whereas the higher ketones form the S enantiomer.

Original languageEnglish (US)
Pages (from-to)162-169
Number of pages8
JournalJournal of the American Chemical Society
Volume108
Issue number1
DOIs
StatePublished - Jan 1 1986

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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