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

• Tipo: Artigo em Revista Científica Internacional
• Data: 2015

Autores

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

Revista

Título: Angewandte Chemie - International Edition

Vol. 54

Páginas: 11063-11067

ISSN: 1433-7851

Editora: Wiley-Blackwell

Indexação

ISI Web of Knowledge - 33 Citações

Scopus - 38 Citações

Outras Informações

ID Authenticus: 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.

Idioma: Inglês

Tipo (Avaliação Docente): Científica

Nº de páginas: 5