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Journal of Bacteriology, April 2006, p. 2919-2927, Vol. 188, No. 8
0021-9193/06/$08.00+0     doi:10.1128/JB.188.8.2919-2927.2006
Copyright © 2006, American Society for Microbiology. All Rights Reserved.

Aerobic Benzoyl-Coenzyme A (CoA) Catabolic Pathway in Azoarcus evansii: Conversion of Ring Cleavage Product by 3,4-Dehydroadipyl-CoA Semialdehyde Dehydrogenase

Johannes Gescher,1 Wael Ismail,1 Ellen Ölgeschläger,1 Wolfgang Eisenreich,2 Jürgen Wörth,3 and Georg Fuchs1*

Mikrobiologie, Institut für Biologie II, Universität Freiburg, Freiburg, Germany,1 Lehrstuhl für Organische Chemie und Biochemie, Technische Universität München, Munich, Germany,2 Institut für organische Chemie und Biochemie, Fakultät für Chemie, Universität Freiburg, Albertstr. 21, D-79104 Freiburg, Germany3

Received 14 December 2005/ Accepted 27 January 2006

Benzoate, a strategic intermediate in aerobic aromatic metabolism, is metabolized in various bacteria via an unorthodox pathway. The intermediates of this pathway are coenzyme A (CoA) thioesters throughout, and ring cleavage is nonoxygenolytic. The fate of the ring cleavage product 3,4-dehydroadipyl-CoA semialdehyde was studied in the ß-proteobacterium Azoarcus evansii. Cell extracts contained a benzoate-induced, NADP+-specific aldehyde dehydrogenase, which oxidized this intermediate. A postulated putative long-chain aldehyde dehydrogenase gene, which might encode this new enzyme, is located on a cluster of genes encoding enzymes and a transport system required for aerobic benzoate oxidation. The gene was expressed in Escherichia coli, and the maltose-binding protein-tagged enzyme was purified and studied. It is a homodimer composed of 54 kDa (without tag) subunits and was confirmed to be the desired 3,4-dehydroadipyl-CoA semialdehyde dehydrogenase. The reaction product was identified by nuclear magnetic resonance spectroscopy as the corresponding acid 3,4-dehydroadipyl-CoA. Hence, the intermediates of aerobic benzoyl-CoA catabolic pathway recognized so far are benzoyl-CoA; 2,3-dihydro-2,3-dihydroxybenzoyl-CoA; 3,4-dehydroadipyl-CoA semialdehyde plus formate; and 3,4-dehydroadipyl-CoA. The further metabolism is thought to lead to 3-oxoadipyl-CoA, the intermediate at which the conventional and the unorthodox pathways merge.

* Corresponding author. Mailing address: Mikrobiologie, Institut Biologie II, Schänzlestr. 1, D-79104 Freiburg, Germany. Phone: (49) 761-2032649. Fax: (49) 761-2032626. E-mail: georg.fuchs{at}biologie.uni-freiburg.de.

Journal of Bacteriology, April 2006, p. 2919-2927, Vol. 188, No. 8
0021-9193/06/$08.00+0     doi:10.1128/JB.188.8.2919-2927.2006
Copyright © 2006, American Society for Microbiology. All Rights Reserved.



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