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首页> 外文期刊>Applied Microbiology >The Missing Link in Linear Alkylbenzenesulfonate Surfactant Degradation: 4-Sulfoacetophenone as a Transient Intermediate in the Degradation of 3-(4-Sulfophenyl)Butyrate by Comamonas testosteroni KF-1
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The Missing Link in Linear Alkylbenzenesulfonate Surfactant Degradation: 4-Sulfoacetophenone as a Transient Intermediate in the Degradation of 3-(4-Sulfophenyl)Butyrate by Comamonas testosteroni KF-1

机译：线性烷基苯磺酸盐表面活性剂降解中的缺失环节：4-磺基苯乙酮作为瞬变中间体被Comamonas testosteroni KF-1降解3-（4-磺基苯基）丁酸酯

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Biodegradation of the laundry surfactant linear alkylbenzenesulfonate (LAS) involves complex bacterial communities. The known heterotrophic community has two tiers. First, all LAS congeners are oxygenated and oxidized to about 50 sulfophenylcarboxylates (SPC). Second, the SPCs are mineralized. Comamonas testosteroni KF-1 mineralizes 3-(4-sulfophenyl)butyrate (3-C4-SPC). During growth of strain KF-1 with 3-C4-SPC, two transient intermediates were detected in the culture medium. One intermediate was identified as 4-sulfoacetophenone (SAP) (4-acetylbenzenesulfonate) by nuclear magnetic resonance (NMR). The other was 4-sulfophenol (SP). This information allowed us to postulate a degradation pathway that comprises the removal of an acetyl moiety from (derivatized) 3-C4-SPC, followed by a Baeyer-Villiger monooxygenation of SAP and subsequent ester cleavage to yield SP. Inducible NADPH-dependent SAP-oxygenase was detected in crude extracts of strain KF-1. The enzyme reaction involved transient formation of 4-sulfophenol acetate (SPAc), which was completely hydrolyzed to SP and acetate. SP was subject to NADH-dependent oxygenation in crude extract, and 4-sulfocatechol (SC) was subject to oxygenolytic ring cleavage. The first complete degradative pathway for an SPC can now be depicted with 3-C4-SPC: transport, ligation to a coenzyme A (CoA) ester, and manipulation to allow abstraction of acetyl-CoA to yield SAP, Baeyer-Villiger monooxygenation to SPAc, hydrolysis of the ester to acetate and SP, monooxygenation of SP to SC, the ortho ring-cleavage pathway with desulfonation, and sulfite oxidation.
机译：洗衣表面活性剂线性烷基苯磺酸盐（LAS）的生物降解涉及复杂的细菌群落。已知的异养群体有两个层次。首先，将所有LAS同类物氧化并氧化为约50个磺基苯基羧酸盐（SPC）。其次，SPC是矿化的。睾丸激素睾丸激素KF-1使3-（4-磺基苯基）丁酸酯（3-C4-SPC）矿化。在带有3-C4-SPC的KF-1菌株生长过程中，在培养基中检测到两个瞬时中间体。通过核磁共振（NMR）鉴定出一种中间体为4-磺基乙酰苯（SAP）（4-乙酰基苯磺酸盐）。另一个是4-磺基苯酚（SP）。该信息使我们推测出降解途径，该途径包括从（衍生化的）3-C4-SPC中除去乙酰基部分，然后进行SAP的Baeyer-Villiger单加氧和随后的酯裂解以生成SP。在菌株KF-1的粗提物中检测到了诱导型NADPH依赖性SAP加氧酶。酶反应涉及瞬时形成4-磺基苯酚乙酸酯（SPAc），该酯被完全水解为SP和乙酸酯。 SP受到粗提物中NADH依赖性氧合，而4-磺基邻苯二酚（SC）受到氧解环裂解。现在可以用3-C4-SPC描绘SPC的第一个完整降解途径：转运，与辅酶A（CoA）酯的连接以及进行操作以允许乙酰辅酶A提取以产生SAP，Baeyer-Villiger单加氧为SPAc ，酯水解成乙酸酯和SP，SP变成SC的单加氧，带有脱硫的邻环裂解途径以及亚硫酸盐氧化。

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