Pheromones play important roles in chemical communication among organisms. Various chiral and non-racemic pheromones have been identified since the late 1960s. Their enantioselective syntheses could establish the absolute configuration of the naturally occurring pheromones and clarified the relationships between absolute configuration and bioactivity. For example, neither the (R)- nor (S)-enantiomer of sulcatol, the aggregation pheromone of an ambrosia beetle Gnathotrichus sulcatus, is behaviorally active, while their mixture is bioactive. In the case of olean, the olive fruit fly pheromone, its (R)-isomer is active for the males, and the (S)-isomer is active for the females. About 140 chiral pheromones are reviewed with regard to their stereochemistry-bioactivity relationships. Problems encountered in studying chirality of pheromones were examined and analyzed to think about possible future directions in pheromone science.
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Significance of chirality in pheromone science. Journal Published:
PUBLICATION TYPE: Journal Article
Journal: Bioorganic & medicinal chemistry
VOLUME: 15
Page Numbers: 7505-23
Journal Abbreviation: Bioorg. Med. Chem.
ISSN: 0968-0896
DAY: 25
MONTH: 08
YEAR: 2007
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LANGUAGE: eng
NlmUniqueID: 9413298
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AFFILIATION: Photosensitive Materials Research Center, Toyo Gosei Co., Ltd, Wakahagi 4-2-1, Inba-mura, Inba-gun, Chiba 270-609, Japan; RIKEN Research Center for Allergy and Immunology, Hirosawa 2-1, Wako-shi, Saitama 351-0198, Japan.
Country: England
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MEDLINETA: Bioorg Med Chem
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