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Structure of Hierridin C, Synthesis of Hierridins B and C, and Evidence for Prevalent Alkylresorcinol Biosynthesis in Picocyanobacteria

2019-02Journal article Open access
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dc.contributor.authorCosta, Margarida
dc.contributor.authorSampaio-Dias, Ivo E.
dc.contributor.authorCastelo-Branco, Raquel
dc.contributor.authorScharfenstein, Hugo
dc.contributor.authorRezende de Castro, Roberta
dc.contributor.authorSilva, Artur
dc.contributor.authorSchneider, Maria Paula C.
dc.contributor.authorAraújo, Maria João
dc.contributor.authorMartins, Rosário
dc.contributor.authorDomingues, Valentina F.
dc.contributor.authorNogueira, Fátima
dc.contributor.authorCamões, Vera
dc.contributor.authorVasconcelos, Vitor M.
dc.contributor.authorLeão, Pedro N.
dc.date.accessioned2020-10-30T15:02:05Z
dc.date.available2020-10-30T15:02:05Z
dc.date.issued2019-02
dc.description.abstractSmall, single-celled planktonic cyanobacteria are ubiquitous in the world's oceans yet tend not to be perceived as secondary metabolite-rich organisms. Here we report the isolation and structure elucidation of hierridin C, a minor metabolite obtained from the cultured picocyanobacterium Cyanobium sp. LEGE 06113. We describe a simple, straightforward synthetic route to the scarcely produced hierridins that relies on a key regioselective halogenation step. In addition, we show that these compounds originate from a type III PKS pathway and that similar biosynthetic gene clusters are found in a variety of bacterial genomes, most notably those of the globally distributed picocyanobacteria genera Prochlorococcus, Cyanobium and Synechococcus.pt_PT
dc.description.sponsorshipWe thank CEMUP for HRESIMS and NMR analyses. This research was supported by the Structured Program of R&D&I INNOVMAR - Innovation and Sustainability in the Management and Exploitation of Marine Resources (reference NORTE-01-0145-FEDER-000035, Research Line NOVELMAR), funded by the Northern Regional Operational Program (NORTE2020) through the European Regional Development Fund (ERDF). This work was also funded by Fundação para a Ciência e Tecnologia (FCT), under the framework of projects UID/Multi/04423/2013, GHTM - UID/Multi/04413/2013 and PTDC/MAR-BIO/2818/2013, IFCT contract IF/01358/2014 to P.N.L., and Ph.D. scholarship SFRH/BD/93632/2013 to IESD. In addition, this work was also partially supported by the Associate Laboratory for Green Chemistry- LAQV, which is financed by national funds from FCT/MCTES (UID/QUI/50006/2013) and cofinanced by the ERDF under the PT2020 Partnership Agreement (POCI-01-0145-FEDER-007265).pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.doi10.1021/acs.jnatprod.8b01038pt_PT
dc.identifier.issn0163-3864
dc.identifier.urihttp://hdl.handle.net/10400.22/16396
dc.language.isoengpt_PT
dc.publisherACSpt_PT
dc.relationSÍNTESE ENANTIOSSELETIVA E AVALIAÇÃO BIOLÓGICA DE PROLINOMIMÉTICOS DO PLG E GPE
dc.relation.publisherversionhttps://pubs.acs.org/doi/10.1021/acs.jnatprod.8b01038pt_PT
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/pt_PT
dc.subjectAnisolespt_PT
dc.subjectCyanobacteriapt_PT
dc.subjectGenomept_PT
dc.subjectMultigene Familypt_PT
dc.subjectResorcinolspt_PT
dc.subjectBacteriapt_PT
dc.subjectMetabolismpt_PT
dc.subjectAromatic compoundspt_PT
dc.subjectCluster chemistrypt_PT
dc.titleStructure of Hierridin C, Synthesis of Hierridins B and C, and Evidence for Prevalent Alkylresorcinol Biosynthesis in Picocyanobacteriapt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.awardTitleSÍNTESE ENANTIOSSELETIVA E AVALIAÇÃO BIOLÓGICA DE PROLINOMIMÉTICOS DO PLG E GPE
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/5876/UID%2FMulti%2F04413%2F2013/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/5876/UID%2FMulti%2F04423%2F2013/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/5876/UID%2FQUI%2F50006%2F2013/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT//SFRH%2FBD%2F93632%2F2013/PT
oaire.citation.endPage402pt_PT
oaire.citation.issue2pt_PT
oaire.citation.startPage393pt_PT
oaire.citation.titleJournal of Natural Productspt_PT
oaire.citation.volume82pt_PT
oaire.fundingStream5876
oaire.fundingStream5876
oaire.fundingStream5876
person.familyNameDomingues
person.givenNameValentina Maria Fernandes
person.identifier.ciencia-id4E16-791D-6664
person.identifier.orcid0000-0003-3472-849X
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.rightsopenAccesspt_PT
rcaap.typearticlept_PT
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