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Biosynthesis-assisted structural elucidation of the bartolosides, chlorinated aromatic glycolipids from cyanobacteria

2015-07Journal article Open access
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dc.contributor.authorLeão, Pedro N.
dc.contributor.authorNakamura, Hitomi
dc.contributor.authorCosta, Margarida
dc.contributor.authorPereira, Alban R.
dc.contributor.authorMartins, Rosario
dc.contributor.authorVasconcelos, Vítor
dc.contributor.authorGerwick, William H.
dc.contributor.authorBalskus, Emily P.
dc.date.accessioned2016-01-20T13:00:48Z
dc.date.available2016-01-20T13:00:48Z
dc.date.issued2015-07
dc.description.abstractThe isolation of the bartolosides, unprecedented cyanobacterial glycolipids featuring aliphatic chains with chlorine substituents and C-glycosyl moieties, is reported. Their chlorinated dialkylresorcinol (DAR) core presented a major structural-elucidation challenge. To overcome this, we discovered the bartoloside (brt) biosynthetic gene cluster and linked it to the natural products through in vitro characterization of the DAR-forming ketosynthase and aromatase. Bioinformatic analysis also revealed a novel potential halogenase. Knowledge of the bartoloside biosynthesis constrained the DAR core structure by defining key pathway intermediates, ultimately allowing us to determine the full structures of the bartolosides. This work illustrates the power of genomics to enable the use of biosynthetic information for structure elucidation.pt_PT
dc.identifier.citationLeão, P. N., Nakamura, H., Costa, M., Pereira, A. R., Martins, R., Vasconcelos, V., Gerwick, W. H., & Balskus, E. P. (2015). Biosynthesis-Assisted Structural Elucidation of the Bartolosides, Chlorinated Aromatic Glycolipids from Cyanobacteria. Angewandte Chemie, 127(38), 11215–11219. https://doi.org/10.1002/ange.201503186
dc.identifier.doi10.1002/ange.201503186pt_PT
dc.identifier.issn1521-3773
dc.identifier.urihttp://hdl.handle.net/10400.22/7421
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherWileypt_PT
dc.relation.publisherversionhttp://onlinelibrary.wiley.com/doi/10.1002/ange.201503186/fullpt_PT
dc.titleBiosynthesis-assisted structural elucidation of the bartolosides, chlorinated aromatic glycolipids from cyanobacteriapt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.citation.endPage11219pt_PT
oaire.citation.issue38pt_PT
oaire.citation.startPage11215pt_PT
oaire.citation.titleAngewandte Chemiept_PT
oaire.citation.volume127pt_PT
person.familyNameMartins
person.givenNameRosario
person.identifier.ciencia-idA919-DB40-EF10
person.identifier.orcid0000-0002-9882-4651
person.identifier.scopus-author-id21834368700
rcaap.rightsopenAccesspt_PT
rcaap.typearticlept_PT
relation.isAuthorOfPublication82a7c349-c88e-450f-adc7-3331d69149cf
relation.isAuthorOfPublication.latestForDiscovery82a7c349-c88e-450f-adc7-3331d69149cf

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