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Tissue distribution and substrate specificity of an epoxide hydrase in the gypsy moth,Lymantria dispar
Authors:S. M. Graham  G. D. Prestwich
Affiliation:(1) Present address: Department of Chemistry, State University of New York, 11794-3400 Stony Brook, New York, USA
Abstract:The stereoselectivity of the enzymatic hydration of disparlure, the pheromone for the gypsy mothLymantria dispar, and for twomeso analogues was determined. A single expoxide hydrase (EH), present in various male and female moth tissues, converted disparlure and the analogues to their respectivethreo-(R,R)-diols with high stereoselectivity as determined by analysis of the diols by chiral phase capillary gas chromatography. This EH recognizes thecis-nature of the dialkyl oxirane, but shows poor discrimination of the two alkyl chains.
Keywords:Pheromone analogue  substrate analogue  disparlure  Lymantria dispar  gypsy moth  expoxide hydrase  pheromone metabolism  lipophilic site  epoxide  oxirane  stereoselective hydration
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