Chaxapeptin, a lasso peptide from the extremotolerant Streptomyces leeuwenhoekii strain C58 from the hyper-arid Atacama Desert

Somayah Sameer Elsayed, Franziska Trusch, Hai Deng, Andrea Raab, Ivan Prokes, Kanungnid Busarakam, Juan A Asenjo, Barbara A. Andrews, Pieter van West, Alan T. Bull, Michael Goodfellow, Yu Yi, Rainer Ebel, Marcel Jaspars, Mostafa Rateb*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

64 Citations (Scopus)

Abstract

Lasso peptides are ribosomally synthesized and post-translationally modified peptides (RiPPs) that possess a unique “lariat knot” structural motif. Genome mining-targeted discovery of new natural products from microbes obtained from extreme environments has led to the identification of a gene cluster directing the biosynthesis of a new lasso peptide, designated as chaxapeptin 1, in the genome of Streptomyces leeuwenhoekii strain C58 isolated from the Atacama Desert. Subsequently, 1 was isolated and characterized using high-resolution electrospray ionization mass spectrometry and nuclear magnetic resonance methods. The lasso nature of 1 was confirmed by calculating its nuclear Overhauser effect restraint-based solution structure. Chaxapeptin 1 displayed a significant inhibitory activity in a cell invasion assay with human lung cancer cell line A549.

Original languageEnglish
Pages (from-to)10252-10260
Number of pages9
JournalThe Journal of Organic Chemistry
Volume80
Issue number20
Early online date24 Sep 2015
DOIs
Publication statusPublished - 16 Oct 2015
Externally publishedYes

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