Biosynthesis-Assisted Structural Elucidation of the Bartolosides, Chlorinated Aromatic Glycolipids from Cyanobacteria

• Type: Article in International Scientific Journal
• Date: 2015

Authors

Pedro N Leão (Author) Other; Hitomi Nakamura (Author) Other; Margarida Costa (Author) Other; Alban R Pereira (Author) Other; Rosário Martins (Author) Other; Vitor Vasconcelos (Author) Other; William H Gerwick (Author) Other; Emily P Balskus (Author) Other

Journal

Title: Angewandte Chemie - International Edition

Vol. 54

Pages: 11063-11067

ISSN: 1433-7851

Publisher: Wiley-Blackwell

Indexing

ISI Web of Knowledge - 33 Citations

Scopus - 38 Citations

Other information

Authenticus ID: P-00G-N4K

DOI: 10.1002/anie.201503186

Abstract (EN): 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.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 5