Regio- And Stereoselective Hydrogenation of 2-demethoxy-2’-methyldehydrogriseofulvin, A Symmetrical Substrate, To (+)-2-demethoxy-2/-methylgriseofulvin With A Cell-free System of Streptomyces Cinereocrocatus

Taiko Oda, Humie Hashimoto, Yoshihiro Sato

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Enzymatic hydrogenation of 2 ‘-demethoxy-2’-methyldehydrogriseofulvin (5) with a cell-free system of Streptomyces cinereocrocatus afforded (+)-2/-demethoxy-2'-methylgriseofulvin (6). The structure of 6 was determined on the basis of comparisons of the proton nuclear magnetic resonance spectrum, mass spectrum, and circular dichroism with those of a standard specimen which was synthesized chemically. The results demonstrated that when the 2’-position of (—)-dehydrogriseofulvin was substituted with a methyl group, its hydrogenation with the cell-free system occurred stereoselectively at the 5 ‘,6’-position.

Original languageEnglish
Pages (from-to)525-528
Number of pages4
JournalChemical and Pharmaceutical Bulletin
Volume38
Issue number2
DOIs
Publication statusPublished - 1990 Jan 1

Keywords

  • 2'-demethoxy-2/-methylgriseofulvin methylation of α
  • cell-free system Streptomyces cinereocrocatus NRRL 3443 stereochemistry 2
  • demethoxy-2'methyl-dehydrogriseofulvin
  • unsaturated compound enzymatic hydrogenation

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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