Regioselective enzymatic acylation and deacetylation of secoiridoid glucosides

Chem Pharm Bull (Tokyo). 2009 Aug;57(8):882-4. doi: 10.1248/cpb.57.882.

Abstract

Candida antarctica lipase (CAL) catalyses the regioselective cinnamoylation and benzoylation of the aglycone moiety of 10-hydroxyoleoside dimethyl ester a secoiridoid glucoside. This enzyme catalyses as well regioselective deacetylation of the aglycone moiety of 10,2',3',4',6'-pentaacetoxyoleoside dimethyl ester. Further action of the enzyme results in deacetylation at C-6' and C-4' of the glucoside moiety.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylation
  • Acylation
  • Candida / enzymology*
  • Catalysis
  • Iridoids / chemistry*
  • Lipase / metabolism*
  • Magnetic Resonance Spectroscopy / standards
  • Molecular Conformation
  • Reference Standards
  • Stereoisomerism

Substances

  • Iridoids
  • Lipase