Absolute configuration of 2-sec-butyl-4,5-dihydrothiazole in male mouse urine.
The absolute configuration of 2-sec-butyl-4,5-dihydrothiazole (DHT) in urine of adult male mice was determined through chiral trifluoroacetyl derivative capillary chromatography by comparing the retention time with synthetic standards. (S)-DHT was extracted from fresh urine, while neither (R)-DHT nor the racemization of (S)-DHT were detected. We can conclude that DHT in urine possesses the S configuration, although we cannot exclude a minor component in the R configuration. (S)-DHT was then characterized for binding to the complex of major urinary proteins of male mouse urine (MUP) and for a behavioral response, the competitive scent marking behavior (countermarking). The binding constant of (S)-DHT to MUP (determined by competitive displacement) was 8.2 +/- 0.6 microM (mean +/- SD) and was 10.5 +/- 0.6 microM for R-DHT, thus excluding a relevant difference in binding. (S)-DHT modified countermarking in a peculiar way. Male mice were slow in countermarking urinary spots streaked 2 days earlier and on top of which (S)-DHT was added shortly before the test. This response was not seen when adding (S)-DHT to freshly streaked urinary spots or to clean paper. Unlike (S)-DHT, (R)-DHT prompted countermarking rather than delaying it. We can further conclude that (S)-DHT in male mouse urine is an aversive chemosignal for countermarking.
Cavaggioni
Andrea
A
Dipartimento di Anatomia e Fisiologia Umana, Università di Padova, 35100 Padova, Italy. andrea.cavaggioni@unipd.it
Mucignat-Caretta
Carla
C
Zagotto
Giuseppe
G
D000818:Animals; D001522:Behavior, Animal / Q000187:drug effects; D002849:Chromatography, Gas; D003163:Competitive Behavior / Q000187:drug effects; D008297:Male; D051379:Mice; D010675:Pheromones / Q000737:chemistry / Q000652:urine; D011485:Protein Binding / Q000187:drug effects; D011719:Pyrazines / Q000494:pharmacology; D013237:Stereoisomerism; D013844:Thiazoles / Q000737:chemistry* / Q000494:pharmacology / Q000652:urine*
D010675:Pheromones; D011719:Pyrazines; D013844:Thiazoles; C049351:2-(sec-butyl)-4,5-dihydrothiazole; C034376:2-isobutyl-3-methoxypyrazine