This Article Full Text (PDF) Alert me when this article is cited Alert me if a correction is posted Services Similar articles in this journal Similar articles in PubMed Alert me to new issues of the journal Download to citation manager Reprints and Permissions Copyright Information Books from ASM Press MicrobeWorld Citing Articles Citing Articles via HighWire Citing Articles via Google Scholar Google Scholar Articles by Bartholomew, B. A. Articles by Hopper, D. J. Search for Related Content PubMed PubMed Citation Articles by Bartholomew, B. A. Articles by Hopper, D. J. Agricola Articles by Bartholomew, B. A. Articles by Hopper, D. J.

 Previous Article  |  Next Article 

Appl. Environ. Microbiol., Sep 1996, 3245-3250, Vol 62, No. 9
Copyright © 1996, American Society for Microbiology

Atropine Metabolism by Pseudomonas sp. Strain AT3: Evidence for Nortropine as an Intermediate in Tropine Breakdown and Reactions Leading to Succinate

BA Bartholomew, MJ Smith, PW Trudgill and DJ Hopper
Institute of Biological Sciences, University of Wales, Aberystwyth, Dyfed SY23 3DD, United Kingdom

Pseudomonas strain AT3, isolated by elective culture with atropine, hydrolyzed atropine and grew diauxically, first on the tropic acid and then on the tropine. Tropine was also used as a sole carbon and energy source. The methyl group of tropine was eliminated as formaldehyde, and the nortropine thus formed was a precursor of 6-hydroxycyclohepta-1,4-dione. Ammonia was detected as a product of nitrogen elimination. 6-Hydroxycyclohepta-1,4-dione was oxidized to cyclohepta-1,3,5-trione by an induced NAD(sup+)-specific dehydrogenase. Although cyclohepta-1,3,5-trione is a (beta)-diketone with two potential hydrolytic cleavage sites, an induced hydrolase was specific for one of these sites, with 4,6-dioxoheptanoate as the only hydrolysis product. Unlike the alternative cleavage product (3,6-dioxoheptanoate), this compound is also a (beta)-diketone, and a second hydrolytic cleavage formed succinate and acetone. Although Pseudomonas strain AT3 was not capable of growth with acetone, the compound was not detected in the culture medium and may have been lost to the atmosphere. Exhaustive experimentation with a wide range of conditions did not result in detection of the enzymes required for cleavage of the carbon-nitrogen bonds leading to the formation of nortropine and 6-hydroxycyclohepta-1,4-dione.

This article has been cited by other articles:

• Grogan, G., Roberts, G. A., Bougioukou, D., Turner, N. J., Flitsch, S. L. (2001). The Desymmetrization of Bicyclic beta -Diketones by an Enzymatic Retro-Claisen Reaction. A NEW REACTION OF THE CROTONASE SUPERFAMILY. J. Biol. Chem. 276: 12565-12572 [Abstract] [Full Text]