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首页> 美国卫生研究院文献>Biochemical Journal >Microbial metabolism of alkylbenzene sulphonates. Bacterial metabolism of undecylbenzene-p-sulphonate and dodecylbenzene-p-sulphonate
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Microbial metabolism of alkylbenzene sulphonates. Bacterial metabolism of undecylbenzene-p-sulphonate and dodecylbenzene-p-sulphonate

机译：烷基苯磺酸盐的微生物代谢。十一烷基苯对磺酸盐和十二烷基苯对磺酸盐的细菌代谢

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1. A study was made of the biodegradation of alkylbenzene sulphonate homologues, one of the major components of commercially marketed detergents. A Bacillus species was elected for growth on alkylbenzene sulphonate homologues as the sole source of carbon and sulphur. 2. The results from both whole-cell and cell-free systems indicated that the alkyl, aryl and sulphonate moieties of alkylbenzene sulphonate homologues were all further metabolized by the Bacillus species. 3. The alkyl side chain, after a presumed initial oxidation of the terminal methyl group, was subsequently oxidized by a β-oxidation pathway. Three enzymes of the β-oxidation pathway, i.e. acyl-CoA synthetase, acyl-CoA dehydrogenase and β-hydroxyacyl-CoA dehydrogenase, were identified in cell-free extracts of the detergent-grown Bacillus species. The substrate specificity of acyl-CoA synthetase indicated activity towards several alkylbenzene sulphonate homologues. 4. The sulphonate moiety was released as sulphite by a desulphonating enzyme. Some kinetic properties of this enzyme were determined. The sulphite was subsequently metabolized to either sulphate or adenosine 5′-sulphatophosphate. Two enzymes involved in sulphite metabolism, i.e. sulphite–cytochrome c reductase and adenosine 5′-sulphatophosphate–cytochrome c reductase were detected in cell-free extracts of undecylbenzene-p-sulphonate-grown Bacillus species. 5. The combined results of continuous sampling programmes monitored by both t.l.c. and sulphite appearance in the growth medium indicated that desulphonation of the aromatic moiety was the likely first step in the overall biodegradation of several alkylbenzene sulphonate homologues. 6. The presence of p-hydroxyphenylpropionate, p-hydroxybenzoate and 3,4-dihydroxybenzoate in cells after growth on several alkylbenzene sulphonate homologues containing an odd number of carbon atoms in the side chain was confirmed by g.l.c. and t.l.c. analysis. Cells grown on several homologues containing an even number of carbon atoms in the side chain were shown to contain p-hydroxyphenylacetate and 3,4-dihydroxyphenylacetate. 7. The aromatic nucleus obtained from undecylbenzene-p-sulphonate was further metabolized by an oxidation sequence involving an `ortho-cleavage' route. 8. An overall metabolic pathway for the biodegradation of various alkylbenzene sulphonate homologues by this Bacillus species is proposed.
机译：1.研究了烷基苯磺酸盐同系物的生物降解，这是市售洗涤剂的主要成分之一。芽孢杆菌属菌种被选为在烷基苯磺酸盐同系物上生长的唯一碳和硫源。 2.来自全细胞和无细胞系统的结果表明，烷基苯磺酸盐同系物的烷基，芳基和磺酸盐部分都被芽孢杆菌属物种进一步代谢。 3.在假定末端甲基被初步氧化后，烷基侧链随后被β-氧化途径氧化。在去垢剂生长的芽孢杆菌属物种的无细胞提取物中鉴定出β-氧化途径的三种酶，即酰基-CoA合成酶，酰基-CoA脱氢酶和β-羟基酰基-CoA脱氢酶。酰基辅酶A合成酶的底物特异性表明对几种烷基苯磺酸盐同源物具有活性。 4.磺酸根部分通过脱磺酸酶释放为亚硫酸盐。确定了该酶的一些动力学性质。随后将亚硫酸盐代谢为硫酸盐或5'-磷酸腺苷。在十一烷基苯-对-磺酸盐生长的芽孢杆菌属物种的无细胞提取物中检测到两种亚硫酸盐代谢相关的酶，即亚硫酸盐-细胞色素c还原酶和腺苷5'-硫酸磷酸酯-细胞色素c还原酶。 5.由t.l.c.监测的连续采样程序的合并结果。生长培养基中亚硫酸盐的出现表明芳族部分的脱磺化是几种烷基苯磺酸盐同系物整体生物降解的第一步。 6.通过g.l.c证实了在侧链上含有奇数碳原子的数个烷基苯磺酸盐同系物上生长后，细胞中存在对羟基苯丙酸酯，对羟基苯甲酸酯和3,4-二羟基苯甲酸酯。和t.l.c.分析。在侧链上含有偶数碳原子的几个同系物上生长的细胞显示含有对羟基苯乙酸盐和3,4-二羟基苯乙酸盐。 7.从十一烷基苯-对磺酸酯获得的芳族核通过涉及“邻位裂解”途径的氧化序列进一步代谢。 8.提出了一种由该芽孢杆菌属物种生物降解各种烷基苯磺酸盐同系物的总代谢途径。

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