Stereoselectivity in mammalian chemical communication: male mouse pheromones.
Two male mouse pheromones, 3,4-dehydro-exo-brevicomin (DHB) and 2-sec-butyldihydrothiazole (SBT), are chiral molecules which were previously tested in their respective bioassays as racemic mixtures. The focus of this study has been to determine the absolute configuration of their natural forms and its relation to stereospecific biological action. DHB was established as the R,R-enantiomer possessing biological activity. Due to an extremely easy racemization of SBT under very mild conditions, enantioselectivity of its transmission and its action at the receptor site appear to be of secondary importance.
Novotny
M V
MV
Department of Chemistry, Indiana University, Bloomington 47405, USA.
Xie
T M
TM
Harvey
S
S
Wiesler
D
D
Jemiolo
B
B
Carmack
M
M
D000818:Animals; D001643:Bridged Bicyclo Compounds / Q000737:chemistry* / Q000494:pharmacology; D019086:Bridged Bicyclo Compounds, Heterocyclic; D004971:Estrus / Q000187:drug effects; D005260:Female; D008297:Male; D051379:Mice; D008810:Mice, Inbred C57BL; D010675:Pheromones / Q000737:chemistry* / Q000494:pharmacology; D013237:Stereoisomerism; D013844:Thiazoles / Q000737:chemistry* / Q000494:pharmacology
D001643:Bridged Bicyclo Compounds; D019086:Bridged Bicyclo Compounds, Heterocyclic; D010675:Pheromones; D013844:Thiazoles; C049351:2-(sec-butyl)-4,5-dihydrothiazole; C040729:3,4-dehydrobrevicomin