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Cacaoidin, First Member of the New Lanthidin RiPP Family.

Angewandte Chemie (International ed. in English)

Authors: Francisco Javier Ortiz-López, Daniel Carretero-Molina, Marina Sánchez-Hidalgo, Jesús Martín, Ignacio González, Fernando Román-Hurtado, Mercedes de la Cruz, Sergio García-Fernández, Fernando Reyes, Julia Patricia Deisinger, Anna Müller, Tanja Schneider, Olga Genilloud

Lantibiotics are ribosomally synthesized and post-translationally modified peptides (RiPPs) characterized by the presence of lanthionine or methyllanthionine rings and their antimicrobial activity. Cacaoidin, a novel glycosylated lantibiotic, was isolated from a Streptomyces cacaoi strain and fully characterized by NMR, mass spectrometry, chemical derivatization approaches and genome analysis. The new molecule combines outstanding structural features, such as a high number of d-amino acids, an uncommon glycosylated tyrosine residue and an unprecedented N,N-dimethyl lanthionine. This latter feature places cacaoidin within a new RiPP family located between lanthipeptides and linaridins, here termed lanthidins. Cacaoidin displayed potent antibacterial activity against Gram-positive pathogens including Clostridium difficile. The biosynthetic gene cluster showed low homology with those of other known lanthipeptides or linaridins, suggesting a new RiPP biosynthetic pathway.

© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

PMID: 32407589

Participating cluster members