Microbial Transformation of (+)- and (−)-Dehydrogriseofulvin by Streptomyces Species Analyzed by 2H Nuclear Magnetic Resonance Spectroscopy

Yoshihiro Sato, Taiko Oda, Hazime Saitô

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Abstract

To elucidate the stereochemical course of the microbial transformation of (+)-dehydrogriseofulvin (DGF) by Streptomyces species, (+)-[5′-2H]DGF, which was obtained by dehydrogenation of (+)-[5′ α,5′ β-2H]epigriseofulvin, was incubated with S. cinereocrocatus. The structure of the product was identified as (+)-[5′ α-2H]griseofulvin (GF) by 2H nuclear magnetic resonance spectroscopy. The results of incubations of (−)- and (+)-DGF with eight Streptomyces species (S. cinereocrocatus, S. roseochromogenus, S. bikiniensis, S. griseinus, S. durhamensis, S. californicus, S. fimbriatus, and S. cinereoruber) showed that (−)- and (+)-DGF were isomerized to each other and converted to (+)-GF as the main product, although some (−)-GF was also formed depending on the microorganisms used. In particular, incubation of (+)-DGF with S. cinereoruber yielded (−)-GF as the main product. In addition, (±)-DGF was transformed by S. cinereocrocatus to the naturally occurring (+)-GF in 48% yield. The enantiomer ratios of DGF and GF obtained by microbial transformation were calculated from the [α]D values of corresponding enantiomer mixtures.

Original languageEnglish
Pages (from-to)2313-2321
Number of pages9
JournalChemical and Pharmaceutical Bulletin
Volume29
Issue number8
DOIs
Publication statusPublished - 1981 Jan 1

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Keywords

  • CD
  • H NMR
  • Streptomyces species
  • enantiomer
  • griseofulvin
  • isomerization
  • microbial transformation
  • optical rotation

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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