Experientia

, Volume 51, Issue 7, pp 738–743 | Cite as

Stereoselectivity in mammalian chemical communication: Male mouse pheromones

  • M. V. Novotny
  • T. -M. Xie
  • S. Harvey
  • D. Wiesler
  • B. Jemiolo
  • M. Carmack
Article

Abstract

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 bioasays 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.

Key words

Male mouse pheromones stereospecific response chromatographic resolution of optical isomers estrus synchronization 

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Copyright information

© Birkhäuser Verlag 1995

Authors and Affiliations

  • M. V. Novotny
    • 1
  • T. -M. Xie
    • 1
  • S. Harvey
    • 1
  • D. Wiesler
    • 1
  • B. Jemiolo
    • 1
  • M. Carmack
    • 1
  1. 1.Department of ChemistryIndiana UniversityBloomingtonUSA

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