Boronic Acids as Mechanistic Probes for the Bacterial Luciferase Reaction


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AHRENS, Matthias, Peter MACHEROUX, Anatol EBERHARD, Sandro GHISLA, Bruce P. BRANCHAUD, J. Woodland HASTINGS, 1991. Boronic Acids as Mechanistic Probes for the Bacterial Luciferase Reaction. In: Photochemistry and Photobiology. 54(2), pp. 295-299. ISSN 0031-8655. eISSN 1751-1097. Available under: doi: 10.1111/j.1751-1097.1991.tb02019.x

@article{Ahrens1991Boron-8538, title={Boronic Acids as Mechanistic Probes for the Bacterial Luciferase Reaction}, year={1991}, doi={10.1111/j.1751-1097.1991.tb02019.x}, number={2}, volume={54}, issn={0031-8655}, journal={Photochemistry and Photobiology}, pages={295--299}, author={Ahrens, Matthias and Macheroux, Peter and Eberhard, Anatol and Ghisla, Sandro and Branchaud, Bruce P. and Hastings, J. Woodland} }

<rdf:RDF xmlns:dcterms="" xmlns:dc="" xmlns:rdf="" xmlns:bibo="" xmlns:dspace="" xmlns:foaf="" xmlns:void="" xmlns:xsd="" > <rdf:Description rdf:about=""> <dspace:hasBitstream rdf:resource=""/> <dcterms:rights rdf:resource=""/> <dcterms:title>Boronic Acids as Mechanistic Probes for the Bacterial Luciferase Reaction</dcterms:title> <dc:contributor>Branchaud, Bruce P.</dc:contributor> <dc:contributor>Macheroux, Peter</dc:contributor> <bibo:uri rdf:resource=""/> <dc:contributor>Eberhard, Anatol</dc:contributor> <dc:creator>Macheroux, Peter</dc:creator> <dc:date rdf:datatype="">2011-03-24T17:44:30Z</dc:date> <dc:contributor>Hastings, J. Woodland</dc:contributor> <dc:format>application/pdf</dc:format> <dcterms:hasPart rdf:resource=""/> <dcterms:abstract xml:lang="eng">Bacterial luciferase uses long chain aldehydes as substrates. Alkylboronic acid analogs of these substrates with chain lengths of C7 and C9 have been synthesized, characterized, and used as mechanistic probes for the light emitting reaction. They behave as inhibitors in the in vitro luminescence reaction. Contrary to an earlier report (Macheroux and Ghisla, 1985, Nachr. Chem. Tech. Lab. 33,785 790) they are not substrates for bacterial luciferase, in that they do not lead to light emission and are not oxidized by the flavin-4a-hydroperoxide to the products boric acid and the corresponding alcohol, as would be expected from a Baeyer-Villiger reaction. However, the particular conformation of a putative boronic acid hydroperoxide at the active center might be such that it would preclude a Baeyer-Villiger fragmentation. Thus, while the results do not support the postulate that luciferase proceeds via a Baeyer-Villiger mechanism, they also do not exclude it. A further observation was that the endogenous light emission (no added aldehyde) decays more rapidly than does the luciferase bound flavin-4a-hydroperoxide. This suggests that the endogenous light is not caused by the decomposition of the flavin-4a-hydroperoxide.</dcterms:abstract> <dc:creator>Ghisla, Sandro</dc:creator> <dcterms:issued>1991</dcterms:issued> <dcterms:available rdf:datatype="">2011-03-24T17:44:30Z</dcterms:available> <dc:language>eng</dc:language> <void:sparqlEndpoint rdf:resource="http://localhost/fuseki/dspace/sparql"/> <dc:contributor>Ghisla, Sandro</dc:contributor> <dcterms:bibliographicCitation>First publ. in: Photochemistry and Photobiology 54 (1991), 2, pp. 295-299</dcterms:bibliographicCitation> <dc:creator>Hastings, J. Woodland</dc:creator> <foaf:homepage rdf:resource="http://localhost:8080/jspui"/> <dc:creator>Ahrens, Matthias</dc:creator> <dc:creator>Branchaud, Bruce P.</dc:creator> <dc:contributor>Ahrens, Matthias</dc:contributor> <dspace:isPartOfCollection rdf:resource=""/> <dc:rights>terms-of-use</dc:rights> <dc:creator>Eberhard, Anatol</dc:creator> <dcterms:isPartOf rdf:resource=""/> </rdf:Description> </rdf:RDF>

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