Paper Report for: Maxwell_2002_Anal.Biochem_305_40
Reference
Title: Simultaneous preparation of both enantiomers of juvenile hormones labeled at C-10 with tritium at high specific activity Maxwell RA, Anderson RJ, Schooley DA Ref: Analytical Biochemistry, 305:40, 2002 : PubMed
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.
        
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Maxwell RA, Anderson RJ, Schooley DA (2002) Simultaneous preparation of both enantiomers of juvenile hormones labeled at C-10 with tritium at high specific activity Analytical Biochemistry305: 40-8
Maxwell RA, Anderson RJ, Schooley DA (2002) Analytical Biochemistry305: 40-8