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Chem. Senses 28: 791-797, 2003
© Oxford University Press 2003

Absolute Configuration of 2-sec-Butyl-4,5-dihydrothiazole in Male Mouse Urine

Andrea Cavaggioni1, Carla Mucignat-Caretta1 and Giuseppe Zagotto2

1 Dipartimento di Anatomia e Fisiologia Umana, Università di Padova, 35100 Padova, Italy 2 Dipartimento di Chimica Farmaceutica, Università di Padova, 35100 Padova, Italy

Correspondence to be sent to: Andrea Cavaggioni, Dipartimento di Anatomia e Fisiologia Umana, Università di Padova, 35100 Padova, Italy. e-mail: andrea.cavaggioni{at}unipd.it

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 µM (mean ± SD) and was 10.5 ± 0.6 µM 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.

Key words: chemosignal, enantiomer, mouse, pheromone, 2-sec-butyl-4,5-dihydrothiazole


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