Journal of Chemical Ecology

, Volume 13, Issue 5, pp 1279–1292 | Cite as

Kinetic resolution of secondary alcohols with commercial lipases

Application to rootworm sex pheromone synthesis
  • Philip E. Sonnet
  • Mary Welch Baillargeon
Article
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Accepted:

Abstract

The relative rates of enzyme-catalyzed esterification of the enantiomers of 2-octanol with various acids were determined for several commercial lipases. Interesterifications and hydrolyses of racemic 2-octanol esters catalyzed by these enzymes were also examined. Novo'sMucor miehei lipase exhibited considerable enantioselectivity and was therefore employed to prepare 8-methyl-2-decanols with high configurational purity at the carbinol carbon. Esters of these alcohols had been previously identified as sexually attractive to several rootworm (Diabrotica) species, and the stereochemistry of those esters had been shown to be critical to the attraction. The enzymatic resolution provides a convenient method to obtain such esters in a desired state of configurational purity.

Key words

Diabrotica sp kinetic resolution lipase methyl carbinol Mucor miehei pheromone western corn rootworm Coleoptera Chrysomelidae 
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Copyright information

© Plenum Publishing Corporation 1987

Authors and Affiliations

  • Philip E. Sonnet
    • 1
  • Mary Welch Baillargeon
    • 1
  1. 1.Animal Biomaterials Research UnitAgricultural Research Service, USDAWyndmoor

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