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Synthesis of carrier-free tritium-labeled queen bee pheromone

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Abstract

A short synthesis of [4,5-3H2] (E)-9-oxo-2-decenoic acid (ODA), a high-specific-activity tritium-containing isotopomer of the queen bee pheromone, is described. Catalytic tritiation of the ketal of ethyl 9-oxo-4-decenoate introduces tritium into two positions, one of which is completely unactivated. Subsequent transformation by selenation, oxidation, and hydrolysis affords the labeled 9-ODA at >60 Ci/mmol. The material is suitable for biochemical studies of binding and catabolism in ovarian, antennal, and other target tissues.

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Author notes

  1. Francis X. Webster

    Present address: Department of Chemistry, College of Environmental Science and Forestry, State University of New York, 13210, Syracuse, New York

Authors and Affiliations

  1. Department of Chemistry, State University of New York, 11794-3400, Stony Brook, New York

    Glenn D. Prestwich

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  1. Francis X. Webster
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  2. Glenn D. Prestwich
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Additional information

Fellow of the Alfred P. Sloan Foundation (1981–1985) and Camille and Henry Dreyfus Teacher-Scholar (1981–1986).

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Webster, F.X., Prestwich, G.D. Synthesis of carrier-free tritium-labeled queen bee pheromone. J Chem Ecol 14, 957–962 (1988). https://doi.org/10.1007/BF01018786

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  • DOI: https://doi.org/10.1007/BF01018786

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