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

Research output: Contribution to journalArticle

45 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
JournalJournal of Organic Chemistry
Volume80
Issue number20
Early online date24 Sep 2015
DOIs
Publication statusPublished - 2015

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Genes
Peptides
Electrospray ionization
Biosynthesis
Biological Products
Mass spectrometry
Assays
Cells
Nuclear magnetic resonance
alachlor

Keywords

  • Lasso peptides
  • Hyperarid Atacama Desert

Cite this

Chaxapeptin, a Lasso Peptide from Extremotolerant Streptomyces leeuwenhoekii Strain C58 from the Hyperarid Atacama Desert. / Elsayed, Somayah S; Trusch, Franziska; Deng, Hai; Raab, Andrea; Prokes, Ivan; Busarakam, Kanungnid; Asenjo, Juan A; Andrews, Barbara A; van West, Pieter; Bull, Alan T; Goodfellow, Michael; Yi, Yu; Ebel, Rainer; Jaspars, Marcel; Rateb, Mostafa E.

In: Journal of Organic Chemistry, Vol. 80, No. 20, 2015, p. 10252-10260.

Research output: Contribution to journalArticle

Elsayed, SS, Trusch, F, Deng, H, Raab, A, Prokes, I, Busarakam, K, Asenjo, JA, Andrews, BA, van West, P, Bull, AT, Goodfellow, M, Yi, Y, Ebel, R, Jaspars, M & Rateb, ME 2015, 'Chaxapeptin, a Lasso Peptide from Extremotolerant Streptomyces leeuwenhoekii Strain C58 from the Hyperarid Atacama Desert', Journal of Organic Chemistry, vol. 80, no. 20, pp. 10252-10260. https://doi.org/10.1021/acs.joc.5b01878
Elsayed, Somayah S ; Trusch, Franziska ; Deng, Hai ; Raab, Andrea ; Prokes, Ivan ; Busarakam, Kanungnid ; Asenjo, Juan A ; Andrews, Barbara A ; van West, Pieter ; Bull, Alan T ; Goodfellow, Michael ; Yi, Yu ; Ebel, Rainer ; Jaspars, Marcel ; Rateb, Mostafa E. / Chaxapeptin, a Lasso Peptide from Extremotolerant Streptomyces leeuwenhoekii Strain C58 from the Hyperarid Atacama Desert. In: Journal of Organic Chemistry. 2015 ; Vol. 80, No. 20. pp. 10252-10260.
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title = "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.",
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note = "Acknowledgment We 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.",
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AU - Elsayed, Somayah S

AU - Trusch, Franziska

AU - Deng, Hai

AU - Raab, Andrea

AU - Prokes, Ivan

AU - Busarakam, Kanungnid

AU - Asenjo, Juan A

AU - Andrews, Barbara A

AU - van West, Pieter

AU - Bull, Alan T

AU - Goodfellow, Michael

AU - Yi, Yu

AU - Ebel, Rainer

AU - Jaspars, Marcel

AU - Rateb, Mostafa E

N1 - Acknowledgment We 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.

PY - 2015

Y1 - 2015

N2 - 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.

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