Microbial Transformation of (+)- and (−)-2′-Demethoxydehydro-griseofulvin by Streptomyces cinereocrocatus

Taiko Oda, Yoshihiro Sato

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

To elucidate the microbial activities of Streptomyces cinereocrocatus, (+)- and (—)-2′- demethoxydehydrogriseofulvin (1c and 3c) were synthesized and subjected to microbial transformation. The microbial transformation of the (—)-enantiomer (3c) afforded (+)-2′-demethoxy-2′,3′-dihydrodehydrogriseofulvin (18) as the sole product in a high yield (60%). On the other hand, the microbial transformation of the (+)-enantiomer (1c) gave (+)-2′-demethoxygriseofulvin (6) (12%) and a mixture of (—)- and (+)-2′-demethoxy-2′,3′-dihydrodehydrogriseofulvin (14 and 18) (8%). The results indicate that the microbial transformations take place directly and/or after isomerization with hydrogenations, depending on the kinds of substrates concerned, i.e., (+)- and (—)-2′-demethoxydehydrogriseofulvin analogs. It was concluded that the modes of microbial transformation of dehydrogriseofulvin analogs are greatly influenced by the structure of the substrates, i.e. the substituent at the 2’-position and/or the enantiomeric nature.

Original languageEnglish
Pages (from-to)934-946
Number of pages13
JournalChemical and Pharmaceutical Bulletin
Volume31
Issue number3
DOIs
Publication statusPublished - 1983 Jan 1

Keywords

  • (+)-2’-demethoxygriseofulvin
  • (+)-2′-demethoxy-2′,3’-dihydrodehydrogrieseofulvin
  • (−)-2’-demethoxygriseofulvin
  • (−)-2′-demethoxy-2′,3′-dihydrodehydrogriseofulvin
  • Streptomyces cinereocrocatus
  • cd
  • conformation
  • deuterated derivative
  • enantiomer
  • microbial transformation
  • optical rotation

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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