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J Bacteriol. 1969 March; 97(3): 1192-1197
Copyright © 1969 American Society for Microbiology. All Rights Reserved.

Influence of Side-Chain Substituents on the Position of Cleavage of the Benzene Ring by Pseudomonas fluorescens1

M. M. Seidman, Anne Toms and J. M. Wood

a Department of Chemistry and Chemical Engineering, Division of Biochemistry, University of Illinois, Urbana, Illinois 61801

ABSTRACT

Pseudomonas fluorescens was grown on mineral salts media with phenol, p-hydroxybenzoic acid, p-hydroxy-phenylacetic acid, or p-hydroxy-trans-cinnamic acid as sole carbon and energy source. Each compound was first hydroxylated, ortho to the hydroxyl group on the benzene ring, to give catechol, protocatechuic acid (3,4-dihydroxy-benzoic acid), homoprotocatechuic acid (3,4-dihydroxy-phenylacetic acid), and caffeic acid (3,4-dihydroxy-trans-cinnamic acid), respectively, as the ultimate aromatic products before cleavage of the benzene nucleus. Protocatechuic acid and caffeic acid were shown to be cleaved by ortho fission, via a 3,4-oxygenase mechanism, to give ß-substituted cis, cis-muconic acids as the initial aliphatic products. However, catechol and homoprotocatechuic acid were cleaved by meta fission, by 2,3-and 4,5-oxygenases, respectively, to give {alpha}-hydroxy-muconic semialdehyde and {alpha}-hydroxy-{gamma}-carboxymethyl muconic semialdehyde as initial aliphatic intermediates. Caffeic acid: 3,4-oxygenase, a new oxygenase, consumes 1 mole of O2 per mole of substrate and has an optimal pH of 7.0. The mechanism of cleavage of enzymes derepressed for substituted catechols by P. fluorescens apparently changes from ortho to meta with the increasing nephelauxetic (electron donor) effect of the side-chain substituent.

FOOTNOTES

1 This work was taken in part from a thesis submitted by M. M. Seidman for a B.S. degree in chemistry at the University of Illinois.

J Bacteriol. 1969 March; 97(3): 1192-1197
Copyright © 1969 American Society for Microbiology. All Rights Reserved.





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