Enantioselective Baeyer-Villiger oxidation of bicyclo[3.2.0]hept-2-en-6-One with fungi: optimization of biotransformation and use of TiO2 as support of cell growth

Biotechnol Lett. 2006 Jun;28(11):805-10. doi: 10.1007/s10529-006-9000-3. Epub 2006 May 23.

Abstract

Fungi from Amazonian forest soil (Ecuador) and an Italian factory were screened for Baeyer-Villiger (BV) oxidation of bicyclo [3.2.0]hept-2-en-6-one to 2-oxabicyclo[3.3.0]oct-6-en-3-one (Corey's lactone). Isolates of Fusarium sp. and F. solani produced the (+)-(1R,5S)-lactone while isolates of Aspergillus terricola and A. amazonicus afforded the (-)-(1S,5R)-lactone. Highest conversions (85% yield and 70% enantiomeric excess) were obtained with A. amazonicus grown in presence of 2.7 mM titanium dioxide.

MeSH terms

  • Aspergillus / growth & development
  • Aspergillus / metabolism*
  • Biotransformation / physiology
  • Bridged Bicyclo Compounds / metabolism*
  • Fusarium / growth & development
  • Fusarium / metabolism*
  • Oxidation-Reduction
  • Stereoisomerism
  • Titanium

Substances

  • Bridged Bicyclo Compounds
  • bicyclo(3,2,0)hept-2-en-6-one
  • titanium dioxide
  • Titanium