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Journal of Bacteriology, November 2001, p. 6478-6486, Vol. 183, No. 21
0021-9193/01/$04.00+0   DOI: 10.1128/JB.183.21.6478-6486.2001
Copyright © 2001, American Society for Microbiology. All rights reserved.

Cloning and Characterization of a Gene Cluster for Cyclododecanone Oxidation in Rhodococcus ruber SC1

Kristy Kostichka, Stuart M. Thomas, Katharine J. Gibson, Vasantha Nagarajan, and Qiong Cheng*

Biological and Chemical Sciences and Engineering, Central Research and Development, E. I. DuPont de Nemours, Inc., Wilmington, Delaware 19880-0328

Received 8 March 2001/Accepted 9 August 2001

Biological oxidation of cyclic ketones normally results in formation of the corresponding dicarboxylic acids, which are further metabolized in the cell. Rhodococcus ruber strain SC1 was isolated from an industrial wastewater bioreactor that was able to utilize cyclododecanone as the sole carbon source. A reverse genetic approach was used to isolate a 10-kb gene cluster containing all genes required for oxidative conversion of cyclododecanone to 1,12-dodecanedioic acid (DDDA). The genes required for cyclododecanone oxidation were only marginally similar to the analogous genes for cyclohexanone oxidation. The biochemical function of the enzymes encoded on the 10-kb gene cluster, the flavin monooxygenase, the lactone hydrolase, the alcohol dehydrogenase, and the aldehyde dehydrogenase, was determined in Escherichia coli based on the ability to convert cyclododecanone. Recombinant E. coli strains grown in the presence of cyclododecanone accumulated lauryl lactone, 12-hydroxylauric acid, and/or DDDA depending on the genes cloned. The cyclododecanone monooxygenase is a type 1 Baeyer-Villiger flavin monooxygenase (FAD as cofactor) and exhibited substrate specificity towards long-chain cyclic ketones (C11 to C15), which is different from the specificity of cyclohexanone monooxygenase favoring short-chain cyclic compounds (C5 to C7).

* Corresponding author. Mailing address: E. I. DuPont de Nemours, Inc., Experimental Station, E328/B48, Wilmington, DE 19880-0328. Phone: (302) 695-9952. Fax: (302) 695-1829. E-mail: qiong.cheng{at}usa.dupont.com.

Journal of Bacteriology, November 2001, p. 6478-6486, Vol. 183, No. 21
0021-9193/01/$04.00+0   DOI: 10.1128/JB.183.21.6478-6486.2001
Copyright © 2001, American Society for Microbiology. All rights reserved.


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