Biosynthesis-assisted structural elucidation of the bartolosides, chlorinated aromatic glycolipids from cyanobacteria
- PMID: 26235728
- PMCID: PMC5687511
- DOI: 10.1002/anie.201503186
Biosynthesis-assisted structural elucidation of the bartolosides, chlorinated aromatic glycolipids from cyanobacteria
Erratum in
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Corrigendum: Biosynthesis-Assisted Structural Elucidation of the Bartolosides, Chlorinated Aromatic Glycolipids from Cyanobacteria.Angew Chem Int Ed Engl. 2016 Nov 21;55(48):14895. doi: 10.1002/anie.201609701. Angew Chem Int Ed Engl. 2016. PMID: 27860179 Free PMC article. No abstract available.
Abstract
The 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.
Keywords: biosynthesis; cyanobacteria; dialkylresorcinol; glycolipids; structure elucidation.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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