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 language | English |
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Pages (from-to) | 10252-10260 |
Number of pages | 9 |
Journal | Journal of Organic Chemistry |
Volume | 80 |
Issue number | 20 |
Early online date | 24 Sept 2015 |
DOIs | |
Publication status | Published - 16 Oct 2015 |
Bibliographical note
AcknowledgmentWe thank the College of Physical Sciences, University of Aberdeen, for provision of infrastructure and facilities in the Marine Biodiscovery Centre. S.S.E. thanks the Egyptian Government for the Ph.D. scholarship. K.B. is grateful for a scholarship from the Thai Royal Government, A.T.B. for support from the Royal Society (International Joint Project Grant JP100654), and M.G. for an Emeritus Fellowship from the Leverhulme Trust. J.A.A., B.A.A., and A.T.B. thank Conicyt for the Basal Centre Grant for the CeBiB (Project FB0001). We are indebted to Dr. Byung-Yong Kim (ChunLab, Seoul, Korea) for conducting the fatty acid analyses. F.T. thanks Prof. Peter Bayer for technical advice.
Keywords
- Lasso peptides
- Hyperarid Atacama Desert