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- Title
Biosynthesis-Assisted Structural Elucidation of the Bartolosides, Chlorinated Aromatic Glycolipids from Cyanobacteria.
- Authors
Leão, Pedro N.; Nakamura, Hitomi; Costa, Margarida; Pereira, Alban R.; Martins, Rosário; Vasconcelos, Vitor; Gerwick, William H.; Balskus, Emily P.
- 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.
- Subjects
BIOSYNTHESIS; GLYCOLIPIDS; CYANOBACTERIA; AROMATASE; ACYL carrier protein
- Publication
Angewandte Chemie, 2015, Vol 127, Issue 38, p11215
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201503186