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.
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.
Horinouchi
Masae
M
RIKEN, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan. masae@postman.riken.go.jp
Hayashi
Toshiaki
T
Koshino
Hiroyuki
H
Kurita
Tomokazu
T
Kudo
Toshiaki
T
D001426:Bacterial Proteins / Q000235:genetics / Q000378:metabolism*; D002208:Caproates / Q000737:chemistry / Q000378:metabolism; D020604:Comamonas testosteroni / Q000201:enzymology* / Q000235:genetics / Q000254:growth & development; D015964:Gene Expression Regulation, Bacterial; D006867:Hydrolases / Q000235:genetics / Q000378:metabolism*; D006915:Hydroxytestosterones / Q000737:chemistry / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D013739:Testosterone / Q000378:metabolism*
D001426:Bacterial Proteins; D002208:Caproates; D006915:Hydroxytestosterones; D013739:Testosterone; D006867:Hydrolases