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

doi:10.1021/acs.joc.5b01878

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^* (Corresponding Author)

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

71 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 language	English
Pages (from-to)	10252-10260
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	80
Issue number	20
Early online date	24 Sep 2015
DOIs	https://doi.org/10.1021/acs.joc.5b01878
Publication status	Published - 16 Oct 2015

Keywords

Lasso peptides
Hyperarid Atacama Desert

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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Rainer Ebel
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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

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

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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.",

keywords = "Lasso peptides, Hyperarid Atacama Desert ",

author = "Elsayed, {Somayah S} and Franziska Trusch and Hai Deng and Andrea Raab and Ivan Prokes and Kanungnid Busarakam and Asenjo, {Juan A.} and Andrews, {Barbara A.} and {van West}, Pieter and Bull, {Alan T.} and Michael Goodfellow and Yu Yi and Rainer Ebel and Marcel Jaspars and Rateb, {Mostafa E.}",

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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doi = "10.1021/acs.joc.5b01878",

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T1 - Chaxapeptin, a Lasso Peptide from Extremotolerant Streptomyces leeuwenhoekii Strain C58 from the Hyperarid Atacama Desert

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 - 2015/10/16

Y1 - 2015/10/16

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.

AB - 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.

KW - Lasso peptides

KW - Hyperarid Atacama Desert

U2 - 10.1021/acs.joc.5b01878

DO - 10.1021/acs.joc.5b01878

M3 - Article

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VL - 80

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JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 20

ER -

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

Abstract

Keywords

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