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

Somayah S 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 E Rateb

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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
JournalJournal of Organic Chemistry
Volume80
Issue number20
Early online date24 Sep 2015
DOIs
Publication statusPublished - 2015

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Keywords

  • Lasso peptides
  • Hyperarid Atacama Desert

Cite this

Elsayed, S. S., Trusch, F., Deng, H., Raab, A., Prokes, I., Busarakam, K., Asenjo, J. A., Andrews, B. A., van West, P., Bull, A. T., Goodfellow, M., Yi, Y., Ebel, R., Jaspars, M., & Rateb, M. E. (2015). Chaxapeptin, a Lasso Peptide from Extremotolerant Streptomyces leeuwenhoekii Strain C58 from the Hyperarid Atacama Desert. Journal of Organic Chemistry, 80(20), 10252-10260. https://doi.org/10.1021/acs.joc.5b01878