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Metabolites and dead-end products from the microbial oxidation of quaternary ammonium alcohols

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Abstract

Methyl-triethanol-ammonium originates from the hydrolysis of the parent esterquat surfactant, which is used as softener in fabric care. The initial steps of the catabolism were investigated in cell-free extracts of the bacterial strain MM 1 able to grow with methyl-triethanol-ammonium as sole source of carbon, energy and nitrogen. The initial degradation of methyl-triethanol-ammonium is an enzymatically catalyzed reaction, located in the particulate fraction of strain MM 1. The oxygen dependent reaction occurred also in presence of phenazine methosulfate as an alternative electron acceptor. As soon as one ethanol group of methyl-triethanol-ammonium was oxidized to the aldehyde, cyclic hemiacetals were formed by intramolecular cyclization. The third ethanol group of methyl-triethanol-ammonium was oxidized to the aldehyde and the carboxylic acid sequentially. The structurally related compounds dimethyl-diethanol-ammonium and choline were oxidized as well, whereas (±)-2,3-dihydroxypropyl-trimethyl-ammonium was not converted at all. The structures of the metabolites were established by 1D and 2D 1H, 13C and 14N NMR spectroscopy and by capillary electrophoresis mass spectrometry.

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Abbreviations

CE-MS:

capillary electrophoresis mass spectrometry

DM:

dimethyl-diethanol-ammonium

HMBC:

heteronuclear multiple bond correlation

HMQC:

heteronuclear multiple quantum coherence

HSQC:

heteronuclear single quantum coherence

INT:

iodonitrotetrazolium chloride

MM:

methyl-triethanol-ammonium

PF:

particulate fraction of the cell-free extract

PMS:

phenazine methosulfate

QAA:

quaternary ammonium alcohol

TM:

(±)-2,3-dihydroxypropyl-trimethyl-ammonium

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Authors and Affiliations

  1. Environmental Microbiology, Swiss Federal Institute for Water Resources and Water Pollution Control (EAWAG), P.O. Box 611, Überlandstrasse 133, CH-8600, Dübendorf, Switzerland

    Andres Kaech, Martina Hofer & Thomas Egli

  2. Swiss Federal Laboratories for Materials Testing and Research (EMPA), Überlandstrasse 129, CH-8600, Dübendorf, Switzerland

    Daniel Rentsch

  3. Institute of Organic Chemistry, University of Zurich, Winterthurerstr. 190, CH-8057, Zürich, Switzerland

    Christian Schnider

Authors
  1. Andres Kaech
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  2. Martina Hofer
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  3. Daniel Rentsch
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  4. Christian Schnider
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  5. Thomas Egli
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Correspondence to Thomas Egli.

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Kaech, A., Hofer, M., Rentsch, D. et al. Metabolites and dead-end products from the microbial oxidation of quaternary ammonium alcohols. Biodegradation 16, 461–473 (2005). https://doi.org/10.1007/s10532-004-5164-5

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