High specific activity enantiomerically enriched juvenile hormones: synthesis and binding assay.
- 1 August 1985
- journal article
- research article
- Published by Proceedings of the National Academy of Sciences in Proceedings of the National Academy of Sciences
- Vol. 82 (16) , 5290-5294
- https://doi.org/10.1073/pnas.82.16.5290
Abstract
A stereoselective total synthesis of chiral juvenile hormone I is described that allows stoichiometric introduction of 2 3H atoms in the final step. Both optical antipodes of the pivotal epoxy alcohol intermediate were prepared in 95% enantiomeric excess by the Sharpless epoxidation of a (Z)-allylic alcohol. Elaboration of the hydroxymethyl group to a vinyl group followed by selective homogeneous tritiation affords optically active juvenile hormone I analogs at 58 Ci/mmol. Competitive binding of the labeled 10R, 11S and 10S, 11R enantiomers with unlabeled enantiomers to the hemolymph binding protein of Manduca sexta larvae was determined by using a dextran-coated charcoal assay. The natural 10R, 11S enantiomer has twice the relative binding affinity of the 10S, 11R enantiomer. The availabilty of such high specific activity optically pure hormones will contribute substantially to the search for high-affinity receptors for juvenile hormones in the nuclei of cells. The chiral 12-hydroxy-(10R, 11S)-epoxy intermediate allows modification of juvenile hormone for solid-phase biochemical and radioimmunochemical work without altering either the biologically important carbomethoxy or epoxy recognition sites.This publication has 10 references indexed in Scilit:
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