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PMID: 9603871 Published · ppublish English Journal Article Research Support, Non-U.S. Gov't

Distal cleavage of 3-chlorocatechol by an extradiol dioxygenase to 3-chloro-2-hydroxymuconic semialdehyde.

Journal of bacteriology ·Vol. 180 ·No. 11 ·1998-06-00 ·Pages 2849-53

Riegert U, Heiss G, Fischer P, Stolz A

Abstract

A 2,3-dihydroxybiphenyl 1,2-dioxygenase from the naphthalenesulfonate-degrading bacterium Sphingomonas sp. strain BN6 oxidized 3-chlorocatechol to a yellow product with a strongly pH-dependent absorption maximum at 378 nm. A titration curve suggested (de)protonation of an ionizable group with a pKa of 4.4. The product was isolated, purified, and converted, by treatment with diazomethane, to a dimethyl derivative and, by incubation with ammonium chloride, to a picolinic acid derivative. Mass spectra and 1H and 13C nuclear magnetic resonance (NMR) data for these two derivatives prove a 3-chloro-2-hydroxymuconic semialdehyde structure for the metabolite, resulting from distal (1,6) cleavage of 3-chlorocatechol. 3-Methylcatechol and 2,3-dihydroxybiphenyl are oxidized by this enzyme, in contrast, via proximal (2,3) cleavage.

MeSH Terms
Aldehydes/chemistry Ammonium Chloride Catechols/chemistry Diazomethane Dioxygenases Escherichia coli/enzymology Hydrogen-Ion Concentration Hydrolases/metabolism Mass Spectrometry Models, Chemical Nuclear Magnetic Resonance, Biomolecular Oxygenases/metabolism Picolinic Acids/chemistry Proteins Sorbic Acid/analogs & derivatives,chemistry
Chemicals
3-chloro-2-hydroxymuconic semialdehyde Aldehydes Catechols Picolinic Acids Proteins Ammonium Chloride 3-methylcatechol 3-chlorocatechol Diazomethane Oxygenases Dioxygenases 2,3-dihydroxybiphenyl oxygenase Hydrolases 2-hydroxymuconate-semialdehyde hydrolase Sorbic Acid
Authors & Affiliations
4 authors, click to expand affiliations / ORCID
Riegert U
Institut für Mikrobiologie, Universität Stuttgart, 70569 Stuttgart, Germany.
Heiss G
Fischer P
Stolz A
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Article Info
Journal
Journal of bacteriology
Abbr.
J Bacteriol
ISSN
0021-9193
DOI
10.1128/JB.180.11.2849-2853.1998
Published
1998-06-00
Pages
2849-53
Language
English
Region
United States
NLM ID
2985120R
PMCID
PMC107248
Subset
IM
External Links
PubMed source DOI: 10.1128/JB.180.11.2849-2853.1998 PMC Full Text View journal details
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