在睾丸酮丛毛单胞菌TA441中鉴定9,17-二氧代-1,2,3,4,10,19-六降雄甾烷-5-羧酸、4-羟基-2-氧代己酸和2-羟基己-2,4-二烯酸以及参与睾酮降解的相关酶。
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.
作者信息
Horinouchi Masae, Hayashi Toshiaki, Koshino Hiroyuki, Kurita Tomokazu, Kudo Toshiaki
机构信息
RIKEN, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan.
出版信息
Appl Environ Microbiol. 2005 Sep;71(9):5275-81. doi: 10.1128/AEM.71.9.5275-5281.2005.
Abstract
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.
摘要
睾丸酮丛毛单胞菌TA441通过A环的芳构化作用，随后进行该环的间位裂解来利用睾酮。间位裂解反应的产物，即4,5-9,10-二裂-3-羟基-5,9,17-三氧代雄甾-1(10),2-二烯-4-酸，由水解酶TesD降解。我们直接分离并鉴定出TesD的两种产物，分别为9,17-二氧代-1,2,3,4,10,19-六降雄甾烷-5-酸和(2Z,4Z)-2-羟基己-2,4-二烯酸。后者是纯的4Z异构体。2-羟基己-2,4-二烯酸由水合酶TesE转化，从反应溶液中分离出的产物被鉴定为2-羟基-4-己-2-烯内酯，这表明TesE的直接产物是4-羟基-2-氧代己酸。
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