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Possible Origin of Modified EAG Activity by Point‐Fluorination of the Insect Pheromone Eldanolide
Author(s) -
Hayase Shuichi,
Renou Michel,
Itoh Toshiyuki
Publication year - 2005
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200400863
Subject(s) - conformational isomerism , chemistry , pheromone , electroantennography , stereochemistry , organic chemistry , botany , molecule , biology
Abstract Conformational analysis with B3LYP/6‐31G* calculations was carried out on the insect pheromone eldanolide and its fluorinated analogues in order to clarify the origin of the differences in pheromone activity between these compounds, as measured by electroantennography (EAG). The calculations indicate that some conformers have a distinctively higher energy than their fluorinated analogues. Significant differences were found between the populations of the preferable conformers of EAG‐active and EAG‐inactive compounds. We suggest that the differences in the populations of the favored conformers of the eldanolide analogues best explain the differences in biological activity according to the position of fluorination. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)