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Synthesis and biological activity of a potent optically pure autoinducer-2 quorum sensing agonist

2019-04Journal article Open access
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dc.contributor.authorAscenso, Osvaldo S.
dc.contributor.authorTorcato, Inês M.
dc.contributor.authorMiguel, Ana Sofia
dc.contributor.authorMarques, João C.
dc.contributor.authorXavier, Karina B.
dc.contributor.authorVentura, M. Rita
dc.contributor.authorMaycock, Christopher D.
dc.date.accessioned2020-03-18T15:37:28Z
dc.date.available2021-04-01T00:30:08Z
dc.date.issued2019-04
dc.description.abstractQuorum sensing (QS) regulates population-dependent bacterial behaviours, such as toxin production, biofilm formation and virulence. Autoinducer-2 (AI-2) is to date the only signalling molecule known to foster inter-species bacterial communication across distantly related bacterial species. In this work, the synthesis of pure enantiomers of C4-propoxy-HPD and C4-ethoxy-HPD, known AI-2 analogues, has been developed. The optimised synthesis is efficient, reproducible and short. The (4S) enantiomer of C4-propoxy-HPD was the most active compound being approximately twice as efficient as (4S)-DPD and ten-times more potent than the (4R) enantiomer. Additionally, the specificity of this analogue to bacteria with LuxP receptors makes it a good candidate for clinical applications, because it is not susceptible to scavenging by LsrB-containing bacteria that degrade the natural AI-2. All in all, this study provides a new brief and effective synthesis of isomerically pure analogues for QS modulation that include the most active AI-2 agonist described so far.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.doi10.1016/j.bioorg.2018.12.022pt_PT
dc.identifier.urihttp://hdl.handle.net/10400.7/944
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherElsevierpt_PT
dc.relationFCTpt_PT
dc.relation.publisherversionhttps://www.sciencedirect.com/science/article/abs/pii/S0045206818306163?via%3Dihubpt_PT
dc.subjectAnti-Bacterial Agentspt_PT
dc.subjectBacterial Proteinspt_PT
dc.subjectCarrier Proteinspt_PT
dc.subjectEscherichia colipt_PT
dc.subjectEscherichia coli Proteinspt_PT
dc.subjectPentanonespt_PT
dc.subjectQuorum Sensingpt_PT
dc.subjectStereoisomerismpt_PT
dc.subjectVibriopt_PT
dc.titleSynthesis and biological activity of a potent optically pure autoinducer-2 quorum sensing agonistpt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.citation.endPage81pt_PT
oaire.citation.startPage75pt_PT
oaire.citation.titleBioorganic Chemistrypt_PT
oaire.citation.volume85pt_PT
rcaap.embargofctJournal copyright policiespt_PT
rcaap.rightsopenAccesspt_PT
rcaap.typearticlept_PT

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