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Applied and Environmental Microbiology, September 2005, p. 5275-5281, Vol. 71, No. 9
0099-2240/05/$08.00+0     doi:10.1128/AEM.71.9.5275-5281.2005
Copyright © 2005, American Society for Microbiology. All Rights Reserved.

Identification of 9,17-Dioxo-1,2,3,4,10,19-Hexanorandrostan-5-oic Acid, 4-Hydroxy-2-Oxohexanoic Acid, and 2-Hydroxyhexa-2,4-Dienoic Acid and Related Enzymes Involved in Testosterone Degradation in Comamonas testosteroni TA441

Masae Horinouchi,1* Toshiaki Hayashi,1 Hiroyuki Koshino,1 Tomokazu Kurita,1 and Toshiaki Kudo1,2

RIKEN, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan,1 Science of Biological Supermolecular Systems, Graduate School of Integrated Science, Yokohama City University, Suehiro, Tsurumi-ku, Yokohama 230-0045, Japan2

Received 19 January 2005/ Accepted 13 April 2005

Comamonas testosteroni TA441 utilizes testosterone via aromatization of the A ring followed by meta-cleavage of the ring. The product of the meta-cleavage reaction, 4,5-9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-dien-4-oic acid, is degraded by a hydrolase, TesD. We directly isolated and identified two products of TesD as 9,17-dioxo-1,2,3,4,10,19-hexanorandrostan-5-oic acid and (2Z,4Z)-2-hydroxyhexa-2,4-dienoic acid. The latter was a pure 4Z isomer. 2-Hydroxyhexa-2,4-dienoic acid was converted by a hydratase, TesE, and the product isolated from the reaction solution was identified as 2-hydroxy-4-hex-2-enolactone, indicating the direct product of TesE to be 4-hydroxy-2-oxohexanoic acid.

* Corresponding author. Mailing address: RIKEN, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan. Phone: 81 48 467 9545. Fax: 81 48 462 4672. E-mail: masae{at}postman.riken.go.jp.

Applied and Environmental Microbiology, September 2005, p. 5275-5281, Vol. 71, No. 9
0099-2240/05/$08.00+0     doi:10.1128/AEM.71.9.5275-5281.2005
Copyright © 2005, American Society for Microbiology. All Rights Reserved.



This article has been cited by other articles:

  • Ma, Y.-F., Zhang, Y., Zhang, J.-Y., Chen, D.-W., Zhu, Y., Zheng, H., Wang, S.-Y., Jiang, C.-Y., Zhao, G.-P., Liu, S.-J. (2009). The Complete Genome of Comamonas testosteroni Reveals Its Genetic Adaptations to Changing Environments. Appl. Environ. Microbiol. 75: 6812-6819 [Abstract] [Full Text]  
  • Horinouchi, M., Hayashi, T., Koshino, H., Malon, M., Yamamoto, T., Kudo, T. (2008). Identification of Genes Involved in Inversion of Stereochemistry of a C-12 Hydroxyl Group in the Catabolism of Cholic Acid by Comamonas testosteroni TA441. J. Bacteriol. 190: 5545-5554 [Abstract] [Full Text]  
  • Gohler, A., Xiong, G., Paulsen, S., Trentmann, G., Maser, E. (2008). Testosterone-inducible Regulator Is a Kinase That Drives Steroid Sensing and Metabolism in Comamonas testosteroni. J. Biol. Chem. 283: 17380-17390 [Abstract] [Full Text]  


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