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微生物对芳基磺酸盐的代谢

Metabolism of arylsulphonates by micro-organisms.

作者信息

Cain R B, Farr D R

出版信息

Biochem J. 1968 Feb;106(4):859-77. doi: 10.1042/bj1060859.

Abstract
  1. Species of Pseudomonas capable of degrading arylsulphonates and detergents of the alkylbenzenesulphonate type were isolated from sewage and river water. 2. Benzenesulphinate, benzenesulphonate and toluene-p-sulphonate were rapidly degraded by these organisms with the release of the sulphonate group as sulphite; detergent homologues with a chain length up to 16 carbon atoms (4-n-hexadecyl-benzenesulphonate) also released sulphite. Sulphite oxidation to sulphate in the medium can occur non-enzymically. 3. Growth on benzenesulphonate and toluene-p-sulphonate elicited a catechol 2,3-oxygenase, which effected a ;meta' cleavage of the ring. The metabolic route for benzenesulphonate was determined as: benzenesulphonate-->catechol-->2-hydroxymuconic semialdehyde-->formate and 4-hydroxy-2-oxovalerate-->acetaldehyde and pyruvate; the enzymes catalysing these steps were all inducible. 4. Toluene-p-sulphonate was degraded via 2-hydroxy-5-methylmuconic semialdehyde to formate and 4-hydroxy-2-oxohexanoate and the latter was cleaved to propionaldehyde and pyruvate. Propionaldehyde and propionate were oxidized rapidly by toluene-p-sulphonate-grown cells but slowly by fumarate-grown organisms. 5. The specificity of the catechol 2,3-oxygenase induced by the arylsulphonates, towards catechol and the methylcatechols, varied during the purification and suggested that 3-methylcatechol was probably oxidized by a separate enzyme. Detergents of the alkylbenzenesulphonate type also induced a catechol 2,3-oxygenase in these bacteria. 6. A few isolates, after growth on benzenesulphonate, opened the ring of catechol by an ;ortho' route to form cis-cis-muconate. The enzymes to degrade this intermediate to beta-oxoadipate were also present in induced cells.
摘要
  1. 从污水和河水中分离出了能够降解芳基磺酸盐和烷基苯磺酸盐型洗涤剂的假单胞菌属菌种。2. 苯亚磺酸盐、苯磺酸盐和对甲苯磺酸盐能被这些微生物迅速降解,磺酸盐基团以亚硫酸盐的形式释放出来;链长至16个碳原子的洗涤剂同系物(4-正十六烷基苯磺酸盐)也能释放亚硫酸盐。亚硫酸盐在培养基中可非酶促氧化为硫酸盐。3. 在苯磺酸盐和对甲苯磺酸盐上生长会诱导产生儿茶酚2,3-加氧酶,该酶能使苯环发生“间位”裂解。确定苯磺酸盐的代谢途径为:苯磺酸盐→儿茶酚→2-羟基粘康酸半醛→甲酸和4-羟基-2-氧代戊酸→乙醛和丙酮酸;催化这些步骤的酶都是可诱导的。4. 对甲苯磺酸盐通过2-羟基-5-甲基粘康酸半醛降解为甲酸和4-羟基-2-氧代己酸,后者裂解为丙醛和丙酮酸。丙醛和丙酸盐能被在对甲苯磺酸盐上生长的细胞迅速氧化,但被在富马酸盐上生长的微生物缓慢氧化。5. 由芳基磺酸盐诱导产生的儿茶酚2,3-加氧酶对儿茶酚和甲基儿茶酚的特异性在纯化过程中有所变化,这表明3-甲基儿茶酚可能由一种单独的酶氧化。烷基苯磺酸盐型洗涤剂在这些细菌中也能诱导产生儿茶酚2,3-加氧酶。6. 一些菌株在苯磺酸盐上生长后,通过“邻位”途径打开儿茶酚环形成顺-顺式粘康酸。诱导细胞中也存在将这种中间体降解为β-氧代己二酸的酶。

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