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J Chem Ecol

Title:		Perfluorinated moth pheromones : Synthesis and electrophysiological activity
Author(s):		Prestwich GD; Sun WC; Mayer MS; Dickens JC;
Address:		"Department of Chemistry, State University of New York, 11794-3400, Stony Brook, New York"
Journal Title:		J Chem Ecol
Year:		1990
Volume:		16
Issue:		6
Page Number:		1761 - 1778
DOI:		10.1007/BF01020493
ISSN/ISBN:		0098-0331 (Print) 0098-0331 (Linking)
Abstract:		"Perfluoroalkyl analogs of pheromone constituents were synthesized and responses from male antennal olfactory receptor neurons from three moth species were recorded during stimulation by these analogs. In each analog, the hydrophobic terminus, either a butyl or hexyl substituent on the (Z)-alkenyl chain, was replaced with a perfluorobutyl (Pfb, C4F9) or perfluorohexyl (Pfh, C6F13) moiety. Perfluoroalkyl analogs were more volatile than their hydrocarbon analogs, showing a decrease in gas chromatographic retention time by two to four methylene equivalents (Kovats retention indices). Specialist neurons of maleHeliothis zea responded to a 0.02-mug dose of (Z)-11-hexadecenal (Z11-16ratioAl) and a dose of 200 mug of Pfb-Z11-16ratioAl with similar spike discharge rates. The HS(a) neurons ofTrichoplusia ni responded to a dose of 0.02 mug ofZ7-14ratioOAc and a dose of 10 mug of Pfb-Z7-12ratioAc with similar discharge rates. The same difference in sensitivity to Pfb-Z7-12ratioOH andZ7-12ratioOH was observed for the responses of the HS(b) neuron and for the responses of theNS(a) neurons to Pfb-Z9-14ratioAc andZ9-14ratioAc. Sensilla ofDiatraea grandiosella similarly showed 100- to 1000-fold greater sensitivity toZ9-16-Al andZ11-16ratioAl than to Pfh-Z9-16ratioAl and Pfb-Z11-16ratioAl. Thus, replacement of terminal alkyl groups with perfluoroalkyl groups in pheromone components produced biologically active compounds with increased volatility and displaced electrophysiological response profiles. Because of the diminished receptor cell sensitivity, we suggest that the binding of the fluorinated analogs to a putative receptor is reduced as a result of less favorable interaction between the hydrophobic protein binding site and the more rigid and more polar perfluoroalkyl moiety"
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Notes:		"PubMed-not-MEDLINEPrestwich, G D Sun, W C Mayer, M S Dickens, J C eng 1990/06/01 J Chem Ecol. 1990 Jun; 16(6):1761-78. doi: 10.1007/BF01020493"