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

Appl Environ Microbiol. 2005 Sep;71(9):5275-81. doi: 10.1128/AEM.71.9.5275-5281.2005.


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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bacterial Proteins / genetics
  • Bacterial Proteins / metabolism*
  • Caproates / chemistry
  • Caproates / metabolism
  • Comamonas testosteroni / enzymology*
  • Comamonas testosteroni / genetics
  • Comamonas testosteroni / growth & development
  • Gene Expression Regulation, Bacterial
  • Hydrolases / genetics
  • Hydrolases / metabolism*
  • Hydroxytestosterones / chemistry
  • Hydroxytestosterones / metabolism
  • Magnetic Resonance Spectroscopy
  • Testosterone / metabolism*


  • Bacterial Proteins
  • Caproates
  • Hydroxytestosterones
  • Testosterone
  • Hydrolases