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Bacterial metabolism of substituted phenols

Oxidation of 4-(Methylmercapto)-and 4-(Methylsulfinyl)-Phenol by Nocardia spec. DSM 43251

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Abstract

4-(Methylmercapto)-phenol (MMP) and 4-(methylsulfinyl)-phenol (MSP) are oxidized by the soil isolate Nocardia spec. DSM 43251, which is closely related to Nocardia calcarea. The rate of degradation depends on the capability of a substrate to support growth and is strongly enhanced in the presence of a second carbon source under the conditions of cooxidation. MMP and MSP are cometabolized by hydroxylation of the benzene ring with the formation of the substituted catechol following by ring cleavage between carbon atoms 2 and 3 (“meta”fission) to give 2-hydroxy-5-methylmercapto-or 2-hydroxy-5-methylsulfinylmuconic semialdehyde. Oxidation of MMP to MSP represents a bypath of MMP-oxidation. The intermediates were identified on the basis of their physical properties. The enzymes responsible for the metabolism of MMP and MSP are induced by growth with MMP or MSP, but not with glucose. MMP- and MSP-induced cells catalyze the oxidation of a variety of substituted phenols. This indicates a rather low substrate specificity of the enzymes induced by MMP and MSP.

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Abbreviations

MMP:

4-(methylmercapto)-phenol

MSP:

4-(methylsulfinyl)-phenol

3M-4MMP:

3-(methyl)-4-(methylmercapto)-phenol

MMC:

4(methylmercapto)-catechol

MSC:

4-(methylsulfonyl)-catechol

MSV:

4-(methylsulfinyl)-veratrol

MSOP:

4-(methylsulfonyl)-phenol

MM-HMSA:

2-hydroxy-5-methylmercaptomuconic semialdehyde

MS-HMSA:

2-hydroxy-5-methylsulfinylmuconic semialdehyde

HMSA:

2-hydroxymuconic semialdehyde

d6-DMSO:

deuterated dimethylsulfoxide

CDCI3 :

deuterochloroform

tlc:

thin layer chromatography

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Authors and Affiliations

  1. Abt. Pflanzenschutz, Bayerische Landesanstalt für Bodenkultur und Pflanzenbau, Menzinger Str. 54, D-8000, München 19, Federal Republic of Germany

    G. Engelhardt, H.G. Rast & P.R. Wallnöfer

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  1. G. Engelhardt
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  2. H.G. Rast
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  3. P.R. Wallnöfer
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Engelhardt, G., Rast, H. & Wallnöfer, P. Bacterial metabolism of substituted phenols. Arch. Microbiol. 114, 25–33 (1977). https://doi.org/10.1007/BF00429626

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  • DOI: https://doi.org/10.1007/BF00429626

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