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  Bioisosteric approach to elucidation of binding of the acetate group of a moth sex pheromone component to its receptor

Gustavsson, A., Tuvesson, M., Larsson, M., Wu, W., Hansson, B., & Liljefors, T. (1997). Bioisosteric approach to elucidation of binding of the acetate group of a moth sex pheromone component to its receptor. Journal of Chemical Ecology, 23(12), 2755-2776. doi:10.1023/A:1022563010599.

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EXT240.pdf (Publisher version), 2MB
 
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 Creators:
Gustavsson, AL, Author
Tuvesson, M, Author
Larsson, MC, Author
Wu, WQ, Author
Hansson, Bill1, Author           
Liljefors, T, Author
Affiliations:
1External Organizations, ou_persistent22              

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Free keywords: SINGLE-SENSILLUM RECORDINGS; CHAIN-ELONGATED ANALOGS; AGROTIS-SEGETUM SCHIFF; TURNIP MOTH; (Z)-5-DECENYL ACETATE; ELECTRON-DIFFRACTION; MOLECULAR MECHANICS; ACETYLACETONE; LEPIDOPTERA; CELLLepidoptera; Noctuidae; Agrotis segetum; (Z)-5-decenyl acetate; pheromone analogs; structure-activity; bioisosteres; single-sensillum recordings; receptor interaction; molecular electrostatic potential; quantum mechanical calculations; ab initio calculations;
 Abstract: A number of analogs of (Z)-5-decenyl acetate, a pheromone component of the turnip moth, Agrotis segetum, in which the acetate group has been replaced by functional groups that may function as bioisosters, have been synthesized and tested using single-cell electrophysiology. The activities have been interpreted in terms of the molecular electrostatic potentials of the polar functional group as calculated by ab initio quantum mechanical calculations. It is concluded that both oxygens of the acetate group in (Z)-5-decenyl acetate contribute to the interactions between the pheromone component and its receptor. Furthermore, the results indicate that the crucial interaction between the carbonyl group and the receptor, which is most probably a hydrogen bonding interaction, takes place in a direction pointing away from the hydrocarbon chain of the pheromone component.

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Language(s): eng - English
 Dates: 1997-12
 Publication Status: Issued
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Type: -
 Identifiers: ISI: 000071144800009
DOI: 10.1023/A:1022563010599
Other: EXT240
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Title: Journal of Chemical Ecology
Source Genre: Journal
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Publ. Info: New York : Plenum Pub. Corp.
Pages: - Volume / Issue: 23 (12) Sequence Number: - Start / End Page: 2755 - 2776 Identifier: ISSN: 0098-0331
CoNE: https://pure.mpg.de/cone/journals/resource/954925466258