On the Regioselectivity of Thioether Formation by Lacticin 481 Synthetase

On the Regioselectivity of Thioether Formation by Lacticin 481 Synthetase

Lantibiotic synthetases generate intramolecular thioether cross-links within peptides through the Michael-type addition of cysteines onto dehydroamino acids originating from Ser and Thr. Presented here is an assay that readily distinguishes between enzymatic and nonenzymatic formation of these cross...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2007-08, Vol.9 (17), p.3343-3346
Hauptverfasser: Zhang, Xingang, Ni, Weijuan, van der Donk, Wilfred A
Format: Artikel
Sprache:eng
Schlagworte:
Bacteriocins
Cysteine - chemistry
Enzymes - metabolism
Peptides - chemistry
Serine - chemistry
Sulfides - chemical synthesis
Threonine - chemistry
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung:Lantibiotic synthetases generate intramolecular thioether cross-links within peptides through the Michael-type addition of cysteines onto dehydroamino acids originating from Ser and Thr. Presented here is an assay that readily distinguishes between enzymatic and nonenzymatic formation of these cross-links. The results demonstrate unequivocally that lacticin 481 synthetase can generate non-native thioether cross-links.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol071301h