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Towards the reaction mechanism of pyrogallol-phloroglucinol transhydroxylase of Pelobacter acidigallici

Towards the reaction mechanism of pyrogallol-phloroglucinol transhydroxylase of Pelobacter acidigallici

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REICHENBECHER, Wolfram, Bernhard SCHINK, 1999. Towards the reaction mechanism of pyrogallol-phloroglucinol transhydroxylase of Pelobacter acidigallici. In: Biochimica et Biophysica Acta / General subjects. 1430(2), pp. 245-253. ISSN 0167-4838

@article{Reichenbecher1999Towar-7220, title={Towards the reaction mechanism of pyrogallol-phloroglucinol transhydroxylase of Pelobacter acidigallici}, year={1999}, doi={10.1016/S0167-4838(99)00004-7}, number={2}, volume={1430}, issn={0167-4838}, journal={Biochimica et Biophysica Acta / General subjects}, pages={245--253}, author={Reichenbecher, Wolfram and Schink, Bernhard} }

<rdf:RDF xmlns:rdf="http://www.w3.org/1999/02/22-rdf-syntax-ns#" xmlns:bibo="http://purl.org/ontology/bibo/" xmlns:dc="http://purl.org/dc/elements/1.1/" xmlns:dcterms="http://purl.org/dc/terms/" xmlns:xsd="http://www.w3.org/2001/XMLSchema#" > <rdf:Description rdf:about="https://kops.uni-konstanz.de/rdf/resource/123456789/7220"> <dc:date rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2011-03-24T17:32:45Z</dc:date> <dcterms:rights rdf:resource="http://nbn-resolving.org/urn:nbn:de:bsz:352-20140905103416863-3868037-7"/> <dcterms:available rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2011-03-24T17:32:45Z</dcterms:available> <dc:format>application/pdf</dc:format> <dcterms:abstract xml:lang="eng">Conversion of pyrogallol to phloroglucinol was studied with the molybdenum enzyme transhydroxylase of the strictly anaerobic fermenting bacterium Pelobacter acidigallici. Transhydroxylation experiments in H 2 18 O revealed that none of the hydroxyl groups of phloroglucinol was derived from water, confirming the concept that this enzyme transfers a hydroxyl group from the cosubstrate 1,2,3,5-tetrahydroxybenzene (tetrahydroxybenzene) to the acceptor pyrogallol, and simultaneously regenerates the cosubstrate. This concept requires a reaction which synthesizes the cofactor de novo to maintain a sufficiently high intracellular pool during growth. Some sulfoxides and aromatic N-oxides were found to act as hydroxyl donors to convert pyrogallol to tetrahydroxybenzene. Again, water was not the source of the added hydroxyl groups; the oxides reacted as cosubstrates in a transhydroxylation reaction rather than as true oxidants in a net hydroxylation reaction. No oxidizing agent was found that supported a formation of tetrahydroxybenzene via a net hydroxylation of pyrogallol. However, conversion of pyrogallol to phloroglucinol in the absence of tetrahydroxybenzene was achieved if little pyrogallol and a high amount of enzyme preparation was used which had been pre-exposed to air. Obviously, the enzyme was oxidized by air to form sufficient amounts of tetrahydroxybenzene from pyrogallol to start the reaction. A reaction mechanism is proposed which combines an oxidative hydroxylation with a reductive dehydroxylation via the molybdenum cofactor, and allows the transfer of a hydroxyl group between tetrahydroxybenzene and pyrogallol without involvement of water. With this, the transhydroxylase differs basically from all other hydroxylating molybdenum enzymes which all use water as hydroxyl source.</dcterms:abstract> <dcterms:title>Towards the reaction mechanism of pyrogallol-phloroglucinol transhydroxylase of Pelobacter acidigallici</dcterms:title> <dc:creator>Reichenbecher, Wolfram</dc:creator> <dcterms:issued>1999</dcterms:issued> <dc:language>eng</dc:language> <dcterms:bibliographicCitation>First publ. in: Biochimica et Biophysica Acta / General subjects, 1430 (1999), pp. 245-253</dcterms:bibliographicCitation> <bibo:uri rdf:resource="http://kops.uni-konstanz.de/handle/123456789/7220"/> <dc:rights>deposit-license</dc:rights> <dc:creator>Schink, Bernhard</dc:creator> <dc:contributor>Schink, Bernhard</dc:contributor> <dc:contributor>Reichenbecher, Wolfram</dc:contributor> </rdf:Description> </rdf:RDF>

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Towards_the_reaction_mechanism_of_pyrogallol_phloroglucinol_transhydroxylase_of_Pelobacter_acidigallici.pdf 157

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