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.
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S.M.G. and G.D.P thank the United States Department of Agriculture for financial support and Dr Y. Masaki (Gifu University, Japan) for a generous gift of authenticthreo-(7S,8S)-2-methyloctadecanediol.
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Graham, S.M., Prestwich, G.D. Tissue distribution and substrate specificity of an epoxide hydrase in the gypsy moth, Lymantria dispar. Experientia 48, 19–21 (1992). https://doi.org/10.1007/BF01923597
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DOI: https://doi.org/10.1007/BF01923597