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The Significance of Chirality: Methods for Determining Absolute Configuration and Optical Purity of Pheromones and Related Compounds

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Techniques in Pheromone Research

Part of the book series: Springer Series in Experimental Entomology ((SSEXP))

Abstract

Since the beginning of pheromone science, the importance of geometrical isomerism in controlling the biological activity of an olefinic pheromone has well been recognized due to the brilliant work of Hecker and Butenandt described in Chapter 1. The importance of optical isomerism or chirality in pheromone perception by insects, however, remained obscure until the mid-1970s. Although Kafka’s (1973) pioneering work demonstrated the behavioral discrimination of the two enantiomers of 4-methylhexanoic acid by the honeybee, a great deal of effort among synthetic chemists was necessary before the complicated stereo-chemistry-pheromone activity relationship became clear. Only after the synthesis of a highly optically pure pheromone is it possible to know something about the stereochemistry-pheromone activity relationship through proper bioassay. The significance of chirality in pheromone perception is now being recognized by proper combination of chiral synthesis and bioassay.

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  1. Department of Agricultural Chemistry, University of Tokyo, 113, Bunkyo-ku, Tokyo, Japan

    Kenji Mori

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  1. Kenji Mori
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  1. Harbor Branch Foundation, 33450, Fort Pierce, Florida, USA

    Hans E. Hummel

  2. Department of Entomology, University of California, 92521, Riverside, California, USA

    Thomas A. Miller

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Mori, K. (1984). The Significance of Chirality: Methods for Determining Absolute Configuration and Optical Purity of Pheromones and Related Compounds. In: Hummel, H.E., Miller, T.A. (eds) Techniques in Pheromone Research. Springer Series in Experimental Entomology. Springer, New York, NY. https://doi.org/10.1007/978-1-4612-5220-7_12

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