Chaxapeptin, a Lasso Peptide from Extremotolerant Streptomyces leeuwenhoekii Strain C58 from the Hyperarid Atacama Desert.

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.

DOI: 10.1021/acs.joc.5b01878

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@article{Elsayed2015ChaxapeptinAL, title={Chaxapeptin, a Lasso Peptide from Extremotolerant Streptomyces leeuwenhoekii Strain C58 from the Hyperarid Atacama Desert.}, author={Somayah Sameer Elsayed and Franziska Trusch and Hai Deng and Andrea Raab and Ivan Prokeŝ and Kanungnid Busarakam and Juan A. Asenjo and Barbara A. Andrews and Pieter van West and Alan T. Bull and Michael J. Goodfellow and Yu Yi and R Ebel and Marcel Jaspars and M E Rateb}, journal={The Journal of organic chemistry}, year={2015}, volume={80 20}, pages={10252-60} }