Syn stereochemistry of cyclic ether formation in 1,8-cineole biosynthesis catalyzed by recombinant synthase from Salvia officinalis

J Am Chem Soc. 2002 Jul 24;124(29):8546-7. doi: 10.1021/ja0265714.

Abstract

Regiospecifically labeled geranyl diphosphates ((2E,6E)-[1,1,8,8,8-(2)H(5)]- and (2E,6Z)-[1,1,9,9,9-(2)H(5)]-GDP) and D(2)O incorporation, in concert with NMR spectrometry, were employed to demonstrate a unique intramolecular syn-facial protonation-cyclization mechanism of action of 1,8-cineole synthase.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Carbon-Carbon Lyases / chemistry*
  • Carbon-Carbon Lyases / metabolism
  • Catalysis
  • Cyclohexanols / chemistry
  • Cyclohexanols / metabolism*
  • Eucalyptol
  • Monoterpenes*
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Proteins / chemistry*
  • Plant Proteins / metabolism
  • Recombinant Proteins / chemistry
  • Recombinant Proteins / metabolism
  • Salvia officinalis / enzymology*
  • Stereoisomerism
  • Terpenes / chemistry
  • Terpenes / metabolism*

Substances

  • Cyclohexanols
  • Monoterpenes
  • Plant Proteins
  • Recombinant Proteins
  • Terpenes
  • 1,8-cineole synthetase
  • Carbon-Carbon Lyases
  • Eucalyptol