Stereochemistry of Hydrogenation of (—)-Dehydrogriseofulvin to (+)-Griseofulvin with a Cell-Free System of Streptomyces cinereocrocatus

Taiko Oda, Yoshihiro Satc

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

To elucidate the stereochemistry of the hydrogenation of(-)-dehydrogriseofulvin (la) to (+)- (3a) by Streptomyces cinereocrocatus, we have prepared from the microorganism a cell- system which can transform la to 3a. The hydrogenation activity of the cell-free system increased in the presence of added reduced nicotinamide adenine dinucleotide phosphate (NADPH). The stereochemistry of hydrogenation was determined by 400 MHz proton nuclear magnetic resonance (1H-NMR) analysis of the products obtained by the enzymatic conversion of (—)-[5/-2H]-dehydrogriseofulvin (lb) and also by the enzymatic conversion of h in medium containing deuterium oxide.

Original languageEnglish
Pages (from-to)1077-1082
Number of pages6
JournalChemical and Pharmaceutical Bulletin
Volume33
Issue number3
DOIs
Publication statusPublished - 1985 Jan 1

Keywords

  • NADPH
  • Streptomyces cinereocrocatus
  • cell-free system
  • dehydrogriseofulvin
  • deuterated compound
  • griseofulvin
  • hydrogenation
  • stereochemistry

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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