Simultaneous preparation of both enantiomers of juvenile hormones labeled at C-10 with tritium at high specific activity.
We report an improved method for the synthesis of high specific activity insect [10-(3)H]juvenile hormones (JH) I, II, and III which affords both enantiomers of each in high optical purity. A synthetic route for JH I was modified to give higher yields and purity. We increased the specific activity of the synthetic [10-(3)H]JHs using normal phase liquid chromatography optimized to give near baseline resolution of [10-(3)H]JHs and unlabeled JHs. Racemic [10-(3)H]JHs and their corresponding diol metabolites were enantiomerically separated using a chiral column eluted with 2-propanol:hexane. Acidic hydration of the unnatural antipode of the [10-(3)H]JHs gives the diol antipode with the same stereochemistry as that from epoxide hydrolase action on the natural JH antipode. The [10-(3)H]JH diol enantiomers can also be resolved with the same chiral column using a more polar solvent. The synthesis of high specific activity chiral ethyl ester analogs of JH I and II can also be accomplished using this synthetic route.
Maxwell
Robert A
RA
Department of Biochemistry, University of Nevada, Reno, NV 89557, USA.
Anderson
Richard J
RJ
Schooley
David A
DA
D000818:Animals; D002728:Chlorohydrins / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D002855:Chromatography, Thin Layer; D007553:Isotope Labeling / Q000379:methods; D007605:Juvenile Hormones / Q000032:analysis / Q000138:chemical synthesis* / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D018402:Manduca; D013058:Mass Spectrometry; D012588:Scintillation Counting; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism; D014316:Tritium
D002728:Chlorohydrins; D007605:Juvenile Hormones; D014316:Tritium