High specific activity enantiomerically enriched juvenile hormones: synthesis and binding assay

Journal Article · Thu Aug 01 04:00:00 EDT 1985 · Proc. Natl. Acad. Sci. U.S.A.; (United States)

DOI:https://doi.org/10.1073/pnas.82.16.5290· OSTI ID:5128045

Prestwich, G D; Wawrzenczyk, C

A stereoselective total synthesis of chiral juvenile hormone I is described that allows stoichiometric introduction of two tritium 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 hydroxy-methyl 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 availability 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. Moreover, 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.

• Research Organization: State Univ. of New York, Stony Brook
• OSTI ID: 5128045
• Journal Information: Proc. Natl. Acad. Sci. U.S.A.; (United States), Journal Name: Proc. Natl. Acad. Sci. U.S.A.; (United States) Vol. 16; ISSN PNASA
• Country of Publication: United States
• Language: English

Related Subjects

550201* -- Biochemistry-- Tracer Techniques
59 BASIC BIOLOGICAL SCIENCES
AFFINITY
ANIMALS
ARTHROPODS
BIOSYNTHESIS
CELL CONSTITUENTS
CELL NUCLEI
CPB
ENANTIOMORPHS
HORMONES
INSECTS
INVERTEBRATES
ISOTOPE APPLICATIONS
LABELLED COMPOUNDS
LARVAE
LEPIDOPTERA
MAGNETIC RESONANCE
MOTHS
NUCLEAR MAGNETIC RESONANCE
RADIOASSAY
RECEPTORS
RESONANCE
STOICHIOMETRY
STRUCTURE-ACTIVITY RELATIONSHIPS
SYNTHESIS
TRACER TECHNIQUES
TRITIUM COMPOUNDS