Literature DB >> 7628582

Stereoselectivity in mammalian chemical communication: male mouse pheromones.

M V Novotny1, T M Xie, S Harvey, D Wiesler, B Jemiolo, M Carmack.   

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 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.

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Year:  1995        PMID: 7628582     DOI: 10.1007/bf01941272

Source DB:  PubMed          Journal:  Experientia        ISSN: 0014-4754


  11 in total

1.  Pheromones: background and potential for use in insect pest control.

Authors:  R M Silverstein
Journal:  Science       Date:  1981-09-18       Impact factor: 47.728

2.  Biological Responses of Atta texana to Its Alarm Pheromone and the Enantiomer of the Pheromone.

Authors:  R G Riley; R M Silverstein; J C Moser
Journal:  Science       Date:  1974-02-22       Impact factor: 47.728

3.  Separation of drug stereoisomers by the formation of beta-cyclodextrin inclusion complexes.

Authors:  D W Armstrong; T J Ward; R D Armstrong; T E Beesley
Journal:  Science       Date:  1986-05-30       Impact factor: 47.728

Review 4.  Chemistry of odor stimuli.

Authors:  G Ohloff
Journal:  Experientia       Date:  1986-03-15

5.  Odor incongruity and chirality.

Authors:  L Friedman; J G Miller
Journal:  Science       Date:  1971-06-04       Impact factor: 47.728

6.  Identification of a testosterone-dependent unique volatile constituent of male mouse urine: 7-exo-ethyl-5-methyl-6,8-dioxabicyclo[3.2.1]-3-octene.

Authors:  M Novotny; F J Schwende; D Wiesler; J W Jorgenson; M Carmack
Journal:  Experientia       Date:  1984-02-15

7.  Investivations on pantothenic acid and its related compounds. 3. Chemical studies. 2. Synthesis of di-D-pantothenoyl-L-cystine.

Authors:  G Ota; O Nagase; Y Hosokawa; H Tagawa; M Shimizu
Journal:  Chem Pharm Bull (Tokyo)       Date:  1967-05       Impact factor: 1.645

8.  Synthetic pheromones that promote inter-male aggression in mice.

Authors:  M Novotny; S Harvey; B Jemiolo; J Alberts
Journal:  Proc Natl Acad Sci U S A       Date:  1985-04       Impact factor: 11.205

Review 9.  The reproductive ecology of the house mouse.

Authors:  F H Bronson
Journal:  Q Rev Biol       Date:  1979-09       Impact factor: 4.875

10.  Promotion of the Whitten effect in female mice by synthetic analogs of male urinary constituents.

Authors:  B Jemiolo; S Harvey; M Novotny
Journal:  Proc Natl Acad Sci U S A       Date:  1986-06       Impact factor: 11.205

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  5 in total

1.  Temperature-dependent spectral density analysis applied to monitoring backbone dynamics of major urinary protein-I complexed with the pheromone 2- sec-butyl-4,5-dihydrothiazole.

Authors:  Hana Krízová; Lukás Zídek; Martin J Stone; Milos V Novotny; Vladimír Sklenár
Journal:  J Biomol NMR       Date:  2004-04       Impact factor: 2.835

2.  High resolution X-ray structures of mouse major urinary protein nasal isoform in complex with pheromones.

Authors:  Samantha Perez-Miller; Qin Zou; Milos V Novotny; Thomas D Hurley
Journal:  Protein Sci       Date:  2010-08       Impact factor: 6.725

3.  Chemical identification of MHC-influenced volatile compounds in mouse urine. I: Quantitative Proportions of Major Chemosignals.

Authors:  Milos V Novotny; Helena A Soini; Sachiko Koyama; Donald Wiesler; Kevin E Bruce; Dustin J Penn
Journal:  J Chem Ecol       Date:  2006-12-27       Impact factor: 2.626

4.  Effect of Male House Mouse Pheromone Components on Behavioral Responses of Mice in Laboratory and Field Experiments.

Authors:  Antonia E Musso; Regine Gries; Huimin Zhai; Stephen Takács; Gerhard Gries
Journal:  J Chem Ecol       Date:  2017-01-27       Impact factor: 2.626

5.  Pheromone binding by polymorphic mouse major urinary proteins.

Authors:  Scott D Sharrow; Jeffrey L Vaughn; Lukás Zídek; Milos V Novotny; Martin J Stone
Journal:  Protein Sci       Date:  2002-09       Impact factor: 6.725

  5 in total

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