Stereospecific Incorporation of Hydrogen from Reduced Nicotinamide Adenine Dinucleotide Phosphate in Hydrogenation of (—)-Dehydrogriseofulvin to (+)-Griseofulvin by a Partially Purified Enzyme System of Streptomyces cinereocrocatus

Taiko Oda, Yoshihiro Sato

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

The stereochemistry of reduced nicotinamide adenine dinucleotide phosphate (NADPH)-dependent hydrogenation was investigated by the conversion of (—)-dehydrogriseofulvin (1) to (+)-griseofulvin (2a) by the use of a partially purified enzyme system of Streptomyces cinereocrocatus in the presence of (4R)- or (4S)-[4-2H1]NADPH. The results of 270 MHz proton nuclear magnetic resonance spectroscopy indicated that the origin of the 6’α-hydrogen of 2a is a hydride ion donated by pro-4R-hydrogen of NADPH.

Original languageEnglish
Pages (from-to)4635-4640
Number of pages6
JournalChemical and Pharmaceutical Bulletin
Volume34
Issue number11
DOIs
Publication statusPublished - 1986 Jan 1

Keywords

  • (4R)-[4-2H1]NADPH
  • (4S)-[4-2H1]-NADPH
  • NADPH
  • Streptomyces cinereocrocatus
  • dehydrogriseofulvin
  • enzyme system
  • griseofulvin
  • hydrogenation

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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