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Chem Senses

Title:		"Absolute configuration of 2-sec-butyl-4,5-dihydrothiazole in male mouse urine"
Author(s):		Cavaggioni A; Mucignat-Caretta C; Zagotto G;
Address:		"Dipartimento di Anatomia e Fisiologia Umana, Universita di Padova, 35100 Padova, Italy. andrea.cavaggioni@unipd.it"
Journal Title:		Chem Senses
Year:		2003
Volume:		28
Issue:		9
Page Number:		791 - 797
DOI:		10.1093/chemse/bjg073
ISSN/ISBN:		0379-864X (Print) 0379-864X (Linking)
Abstract:		"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"
Keywords:		"Animals Behavior, Animal/drug effects Chromatography, Gas Competitive Behavior/drug effects Male Mice Pheromones/chemistry/urine Protein Binding/drug effects Pyrazines/pharmacology Stereoisomerism Thiazoles/*chemistry/pharmacology/*urine;"
Notes:		"MedlineCavaggioni, Andrea Mucignat-Caretta, Carla Zagotto, Giuseppe eng England 2003/12/05 Chem Senses. 2003 Nov; 28(9):791-7. doi: 10.1093/chemse/bjg073"