Stereochemistry of Microbial Transformation of (+)- and (—)-2'-Demethoxydehydrogriseofulvin by Streptomyces cinereocrocatus

Taiko Oda, Yoshihiro Sato

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

To elucidate the stereochemistry of microbial hydrogenation of (+)- and (—)-2'-de-methoxydehydrogriseofulvin (1 and 2) by Streptomyces cinereocrocatus NRRL 3443, deu-terated substrates (la, lb, 2a, and 2b) were synthesized from (+)-griseofulvin (9) and subjected to microbial transformation. The 41.41 MHz 2H nuclear magnetic resonance (NMR) and 400 MHz 1H NMR studies clearly revealed that the microbial hydrogenations of (+)- and ()-2'-demethoxydehydrogriseofulvin (1 and 2) proceed stereospecifically with an anti-addition of hydrogens at the 2' and 3' positions. Further, the microbial transformation of 1 to (+)-2'-demethoxy-2',3'-dihydrodehydrogriseofulvin (5) indicates an isomerization by the microor-ganism of 1 to the enantiomer, (—)-2 '-demethoxydehydrogriseofulvin (2), which is further hydrogenated to afford 5.

Original languageEnglish
Pages (from-to)3446-3453
Number of pages8
JournalChemical and Pharmaceutical Bulletin
Volume31
Issue number10
DOIs
Publication statusPublished - 1983 Jan 1

Keywords

  • 2H NMR
  • Streptomyces cinereocrocatus
  • deuterated (+)-griseofulvin derivative
  • deuterated griseofulvin derivative antibiotic stereochemistry re attack si attack
  • enantiomer
  • microbial transformation

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

Fingerprint Dive into the research topics of 'Stereochemistry of Microbial Transformation of (+)- and (—)-2'-Demethoxydehydrogriseofulvin by Streptomyces cinereocrocatus'. Together they form a unique fingerprint.

  • Cite this