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Synthesis of fluorescent ring-fused 2-pyridone peptidomimetics
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry. Umeå University, Faculty of Medicine, Umeå Centre for Microbial Research (UCMR).
Umeå University, Faculty of Science and Technology, Department of Chemistry.
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2013 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 78, no 23, 12207-12213 p.Article in journal (Refereed) Published
Abstract [en]

Thiazolino fused 2-pyridones peptidomimetics are of significant biological importance due to their ability to interfere with adhesive fiber formation in uropathogenic Escherichia coli and oligomerization of amyloid fibres. We have developed an efficient synthetic route to fluorescent BODIPY analogues, with structural diversification from a key intermediate enabling introduction of C-2 substituents and late incorporation of the BODIPY moiety. A mild lithium halide mediated hydrolysis enabled preparation of peptidomimetic fluorophores with useful photophysical properties for further chemical biology applications.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2013. Vol. 78, no 23, 12207-12213 p.
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:umu:diva-82342DOI: 10.1021/jo401844yPubMedID: 24161000OAI: oai:DiVA.org:umu-82342DiVA: diva2:660714
Funder
Swedish Research Council, 621-2010-4730
Available from: 2013-10-30 Created: 2013-10-30 Last updated: 2017-12-06Bibliographically approved

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Krishnan, K SyamBengtsson, ChristofferGood, James A DMirkhanov, ShamilChorell, ErikJohansson, Lennart B-ÅAlmqvist, Fredrik
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