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Anaerobic degradation of trans-cinnamate and ω-phenylalkane carboxylic acids by the photosynthetic bacterium Rhodopseudomonas palustris: evidence for a β-oxidation mechanism

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Abstract

The mechanism responsible for the initial steps in the anaerobic degradation of trans-cinnamate and ω-phenylalkane carboxylates by the purple non-sulphur photosynthetic bacterium Rhodopseudomonas palustris was investigated. Phenylacetate did not support growth and there was a marked CO2 dependence for growth on acids with greater side-chain lengths. Here, CO2 was presumably acting as a redox sink for the disposal of excess reducing equivalents. Growth on benzoate did not require the addition of exogenous CO2. Aromatic acids with an odd number of side-chain carbon atoms (3-phenylpropionate, 5-phenylvalerate, 7-phenylheptanoate) gave greater apparent molar growth yields than those with an even number of side-chain carbon atoms (4-phenylbutyrate, 6-phenylhexanoate, 8-phenyloctanoate). HPLC analysis revealed that phenylacetate accumulated and persisted in the culture medium during growth on these latter compounds. Cinnamate and benzoate transiently accumulated in the culture medium during growth on 3-phenylpropionate, and benzoate alone accumulated transiently during the course of trans-cinnamate degradation. The transient accumulation of 4-phenyl-2-butenoic acid occurred during growth on 4-phenylbutyrate, and phenylacetate accumulated to a 1:1 molar stoichiometry with the initial 4-phenylbutyrate concentration. It is proposed that the initial steps in the anaerobic degradation of trans-cinnamate and the group of acids from 3-phenylpropionate to 8-phenyloctanoate involves β-oxidation of the side-chain.

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Abbreviations

3-PP:

3-phenylpropionic acid

4-PB:

4-phenylbutyric acid

5-PV:

5-phenylvaleric acid

6-PH:

6-phenylhexanoic acid

7-PH:

7-phenylheptanoic acid

8-PO:

8-phenyloctanoic acid

4-P2B:

4-phenyl-2-butenoic acid

GC/MS:

Gas chromatography/Mass spectrometry

HPLC:

High-pressure liquid chromatography

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Authors and Affiliations

  1. Robert Hill Institute, Department of Molecular Biology and Biotechnology Firth Court, University of Sheffield, Western Bank, P.O. Box 594, S10 2UH, Sheffield, UK

    Douglas J. E. Elder & David J. Kelly

  2. Sittingbourne Research Centre, Shell Research Limited, ME9 8AG, Sittingbourne, UK

    Philip Morgan

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  1. Douglas J. E. Elder
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  2. Philip Morgan
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  3. David J. Kelly
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Elder, D.J.E., Morgan, P. & Kelly, D.J. Anaerobic degradation of trans-cinnamate and ω-phenylalkane carboxylic acids by the photosynthetic bacterium Rhodopseudomonas palustris: evidence for a β-oxidation mechanism. Arch. Microbiol. 157, 148–154 (1992). https://doi.org/10.1007/BF00245283

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  • DOI: https://doi.org/10.1007/BF00245283

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