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

2019Journal 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, Rosario
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.accessioned2019-03-14T14:31:01Z
dc.date.available2019-03-14T14:31:01Z
dc.date.issued2019
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.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.doi10.1021/acs.jnatprod.8b01038pt_PT
dc.identifier.urihttp://hdl.handle.net/10400.22/12978
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherAmerican Chemical Societypt_PT
dc.relation.publisherversionhttps://pubs.acs.org/doi/10.1021/acs.jnatprod.8b01038pt_PT
dc.subjectPicocyanobacteriumpt_PT
dc.subjectbacterial genomespt_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.citation.endPage402pt_PT
oaire.citation.issue2pt_PT
oaire.citation.startPage393pt_PT
oaire.citation.titleJournal of Natural Productspt_PT
oaire.citation.volume82pt_PT
person.familyNameMartins
person.familyNameDomingues
person.givenNameRosario
person.givenNameValentina Maria Fernandes
person.identifier.ciencia-idA919-DB40-EF10
person.identifier.ciencia-id4E16-791D-6664
person.identifier.orcid0000-0002-9882-4651
person.identifier.orcid0000-0003-3472-849X
person.identifier.scopus-author-id21834368700
rcaap.rightsclosedAccesspt_PT
rcaap.typearticlept_PT
relation.isAuthorOfPublication82a7c349-c88e-450f-adc7-3331d69149cf
relation.isAuthorOfPublicationbe653ab6-34ec-4329-972a-eee990a7ec66
relation.isAuthorOfPublication.latestForDiscovery82a7c349-c88e-450f-adc7-3331d69149cf

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