Biotransformation of 4-sec-butylphenol by Gram-positive bacteria of the genera Mycobacterium and Nocardia including modifications on the alkyl chain and the hydroxyl g
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- 作者：Veronika Hahn ; Katharina Sünwoldt…
- 关键词：Degradation ; Environmental pollution ; Hydroxylation ; Glucoside ; Phenylalkane ; Alkylbenzene
- 刊名：Applied Microbiology and Biotechnology
- 出版年：2013
- 出版时间：September 2013
- 年：2013
- 卷：97
- 期：18
- 页码：8329-8339
- 全文大小：340KB
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Katharina Sünwoldt (1)
Annett Mikolasch (1)
Frieder Schauer (1)
1. Institute of Microbiology, Ernst-Moritz-Arndt-University of Greifswald, Friedrich-Ludwig-Jahn-Str. 15, 17487, Greifswald, Germany - ISSN：1432-0614
文摘
The environmental pollutant 4-sec-butylphenol (4-sec-BP) which possesses estrogenic properties was transformed by the aerobic Gram-positive bacteria Mycobacterium neoaurum and Nocardia cyriacigeorgica into three main products (P1–P3) which were isolated and structurally characterized in detail. Two of them were products of a process resembling anaerobic metabolism of alkylphenols based on modifications of the alkyl side chain of 4-sec-BP. The first product (P1) was identified as 4-(2-hydroxy-1-methylpropyl)-phenol. The second product P2 was isolated as a mixture of at least four structures which could be identified as I 4-sec-butylidenecyclohexa-2,5-dienone; II 4-(1-methylenepropyl)-phenol; III 4-(1-methylpropenyl)-phenol; and IV 4-(1-methylallyl)-phenol. In contrast to P1 and P2, the third product (P3) resulted from a modification of the hydroxyl group of 4-sec-BP. This product was only formed by M. neoaurum and was identified as the glucoside conjugate 4-sec-butylphenol-α-d-glucopyranoside. Since in general, fungi synthesize sugar conjugates to detoxify hazardous pollutants, the formation of this conjugate is a peculiarity of M. neoaurum. Thus, altogether, six products were formed from 4-sec-BP and different transformation pathways are introduced. The hydroxylating and glucosylating capacity of the characterized bacteria open up applications in environmental protection.