Lactones. 6. Microbial lactonization of gamma,delta-epoxy esters

Chirality. 2001 Jun;13(6):302-7. doi: 10.1002/chir.1035.

Abstract

The ability of 19 microorganisms to perform the enantioselective lactonization of racemic gamma,delta-epoxy ester 3a and its 7-methyl homolog 3b was checked. It was found that Rhodotorula rubra preferentialy transformed both substrates to (-)-enantiomers of trans delta-hydroxy-gamma-lactones with ee 76% for 3a and 24% for 3b. The best efficiency (20-30%) and enantioselectivity (ee 60-100%) of formation of (-)-gamma-hydroxy-delta-lactones 6a and 6b was observed for lactonization by Botrytis cinerea and Fusarium semitectum, respectively.

MeSH terms

  • Biotransformation
  • Epoxy Compounds / chemistry
  • Epoxy Compounds / metabolism*
  • Esters
  • Fungi / metabolism*
  • Lactones / metabolism*
  • Magnetic Resonance Spectroscopy

Substances

  • Epoxy Compounds
  • Esters
  • Lactones