117940-59-7Relevant academic research and scientific papers
Tritium-Labeled Enantiomers of Disparlure. Synthesis and in Vitro Metabolism
Prestwich, Glenn D.,Graham, Steven McG.,Kuo, Jing-Wen,Vogt, Richard G.
, p. 636 - 642 (1989)
Both of the enantiomers of disparlure, the gypsy moth sex attractant, have been prepared at high specific activity (58 Ci/mmol) by homogeneous tritiation of the optically active alkenyl oxiranes.An improved preparation of the racemic disparlure is also described.The radiolabeled epoxides are cleanly converted to a single product by enzymes isolated from adult gypsy moths (Lymantria dispar).Enzymatic activity obtained from male antennae showed the highest conversion; enzymes isolated from female antennae and from male and female legs showed lower activity.The identification of the metabolite as the threo-7,8-diol is established by independent synthesis and by chemical derivatizations to the diacetate, n-butylboronate, and bis(trimethylsilyl) ether.A symmetrical epoxide analogous to disparlure is converted to a diol product at a significantly lower rate.
