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Applied and Environmental Microbiology, May 2005, p. 2473-2478, Vol. 71, No. 5
0099-2240/05/$08.00+0     doi:10.1128/AEM.71.5.2473-2478.2005
Copyright © 2005, American Society for Microbiology. All Rights Reserved.

Heme-Dependent Rubber Oxygenase RoxA of Xanthomonas sp. Cleaves the Carbon Backbone of Poly(cis-1,4-Isoprene) by a Dioxygenase Mechanism

Reinhard Braaz,1 Wolfgang Armbruster,2 and Dieter Jendrossek1*

Institut für Mikrobiologie, Universität Stuttgart,1 Institut für Lebensmittelchemie, Universität Hohenheim, Stuttgart, Germany2

Received 29 November 2004/ Accepted 2 December 2004

Oxidative cleavage of poly(cis-1,4-isoprene) by rubber oxygenase RoxA purified from Xanthomonas sp. was investigated in the presence of different combinations of 16O2, 18O2, H216O, and H218O. 12-Oxo-4,8-dimethyl-trideca-4,8-diene-1-al (ODTD; m/z 236) was the main cleavage product in the absence of 18O-compounds. Incorporation of one 18O atom in ODTD was found if the cleavage reaction was performed in the presence of 18O2 and H216O. Incubation of poly(cis-1,4-isoprene) (with RoxA) or of isolated unlabeled ODTD (without RoxA) with H218O in the presence of 16O2 indicated that the carbonyl oxygen atoms of ODTD significantly exchanged with oxygen atoms derived from water. The isotope exchange was avoided by simultaneous enzymatic reduction of both carbonyl functions of ODTD to the corresponding dialcohol (12-hydroxy-4,8-dimethyl-trideca-4,8-diene-1-ol (HDTD; m/z 240) during RoxA-mediated in vitro cleavage of poly(cis-1,4-isoprene). In the presence of 18O2, H216O, and alcohol dehydrogenase/NADH, incorporation of two atoms of 18O into the reduced metabolite HDTD was found (m/z 244), revealing that RoxA cleaves rubber by a dioxygenase mechanism. Based on the labeling results and the presence of two hemes in RoxA, a model of the enzymatic cleavage mechanism of poly(cis-1,4-isoprene) is proposed.

* Corresponding author. Mailing address: Institut für Mikrobiologie, Universität Stuttgart, Allmandring 31, 70550 Stuttgart, Germany. Phone: 49-711-685-5483. Fax: 49-711-685-5725. E-mail: dieter.jendrossek{at}imb.uni-stuttgart.de.

Applied and Environmental Microbiology, May 2005, p. 2473-2478, Vol. 71, No. 5
0099-2240/05/$08.00+0     doi:10.1128/AEM.71.5.2473-2478.2005
Copyright © 2005, American Society for Microbiology. All Rights Reserved.



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