Perfluorinated moth pheromones : Synthesis and electrophysiological activity.

摘要: Perfluoroalkyl analogs of pheromone constituents were synthesized and responses from male antennal olfactory receptor neurons three moth species recorded during stimulation by these analogs. In each analog, the hydrophobic terminus, either a butyl or hexyl substituent on (Z)-alkenyl chain, was replaced with perfluorobutyl (Pfb, C4F9) perfluorohexyl (Pfh, C6F13) moiety. more volatile than their hydrocarbon analogs, showing decrease in gas chromatographic retention time two to four methylene equivalents (Kovats indices). Specialist maleHeliothis zea responded 0.02-μg dose (Z)-11-hexadecenal (Z11–16∶Al) 200 μg Pfb-Z11–16∶Al similar spike discharge rates. The HS(a) ofTrichoplusia ni 0.02 ofZ7–14∶OAc 10 Pfb-Z7–12∶Ac same difference sensitivity Pfb-Z7–12∶OH andZ7–12∶OH observed for HS(b) neuron theNS(a) Pfb-Z9–14∶Ac andZ9–14∶Ac. Sensilla ofDiatraea grandiosella similarly showed 100- 1000-fold greater toZ9–16—Al andZ11–16∶Al Pfh-Z9–16∶Al Pfb-Z11–16∶Al. Thus, replacement terminal alkyl groups perfluoroalkyl components produced biologically active compounds increased volatility displaced electrophysiological response profiles. Because diminished cell sensitivity, we suggest that binding fluorinated putative is reduced as result less favorable interaction between protein site rigid polar