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J. Biol. Chem., Vol. 282, Issue 18, 13240-13249, May 4, 2007

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Initial Steps in the Anoxic Metabolism of Cholesterol by the Denitrifying Sterolibacterium denitrificans^*

Yin-Ru Chiang, Wael Ismail, Michael Müller, and Georg Fuchs¹

From the Mikrobiologie, Fakultät für Biologie, Universität Freiburg, Schänzlestrasse 1, D-79104 Freiburg, Germany and the Institut für Pharmazeutische Wissenschaften, Universität Freiburg, Albertstrasse 25, D-79104 Freiburg, Germany

The anoxic metabolism of the ubiquitous triterpene cholesterol is challenging because of its complex chemical structure, low solubility in water, low number of active functional groups, and the presence of four alicyclic rings and two quaternary carbon atoms. Consequently, the aerobic metabolism depends on oxygenase catalyzed reactions requiring molecular oxygen as co-substrate. Sterolibacterium denitrificans is shown to metabolize cholesterol anoxically via the oxidation of ring A, followed by an oxygen-independent hydroxylation of the terminal C-25 of the side chain. The anaerobic hydroxylation of a tertiary carbon using water as oxygen donor is unprecedented and may be catalyzed by a novel molybdenum containing enzyme.

Received for publication, November 28, 2006 , and in revised form, February 15, 2007.

^* This work was supported by the Deutscher Akademischer Austauschdienst (DAAD) through a fellowship to Y.-R. C. The costs of publication of this article were defrayed in part by the payment of page charges. This article must therefore be hereby marked "advertisement" in accordance with 18 U.S.C. Section 1734 solely to indicate this fact.

The on-line version of this article (available at http://www.jbc.org) contains supplemental Fig. S1.

This article was selected as a Paper of the Week.

¹ To whom correspondence should be addressed. Tel.: 497612032649; Fax: 497612032626; E-mail: georg.fuchs{at}biologie.uni-freiburg.de.

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