Downsizing Class II Lasso Peptides: Genome Mining-Guided Isolation of Huascopeptin Containing the First Gly1-Asp7 Macrocycle

Carlos Cortés-Albayay; Scott A Jarmusch; Franziska Trusch; Rainer Ebel; Barbara A Andrews; Marcel Jaspars; Juan A Asenjo

doi:10.1021/acs.joc.9b02231

Downsizing Class II Lasso Peptides: Genome Mining-Guided Isolation of Huascopeptin Containing the First Gly1-Asp7 Macrocycle

Carlos Cortés-Albayay^*
, Scott A Jarmusch
, Franziska Trusch
, Rainer Ebel
, Barbara A Andrews
, Marcel Jaspars
, Juan A Asenjo^*

^*Corresponding author for this work

Universidad de Chile

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

19 Citations (Scopus)

9 Downloads (Pure)

Abstract

A new lasso peptide, huascopeptin, was isolated following genome-mined discovery of a new biosynthetic gene cluster in extremotolerant Streptomyces huasconensis HST28T from Salar de Huasco, Atacama Desert, Chile. Compound 1 is a 13-residue class II lasso peptide containing a novel Gly1-Asp7 macrolactam ring, a three-residue loop, and a three-residue tail, making it the smallest lasso peptide isolated to date. The lasso structure was confirmed using NOE restraint-based molecular dynamics simulations.

Original language	English
Pages (from-to)	1661-1667
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	85
Issue number	3
Early online date	13 Jan 2020
DOIs	https://doi.org/10.1021/acs.joc.9b02231
Publication status	Published - 7 Feb 2020

Bibliographical note

This work was financially supported by the CONICYT PFCHA/DOCTORADO BECAS CHILE/2016-21160585 fellowship and CONICYT Basal Centre Grant for the Centre for Biotechnology and Bioengineering, CeBiB (FB0001). S.A.J. thanks the University of Aberdeen for providing an Elphinstone Scholarship. We thank the Scottish High-Field NMR (SHF NMR) Centre at the University of Edinburgh for NMR experiments. We also thank Dr. Paul Herron (Strathclyde Institute of Pharmacy and Biomedical Sciences) for genome sequencing. Additionally, we thank Kirsti Helland, Marte Albrigsten, and Jeanette Andersen (University of Tromsø - The Arctic University of Norway) for conducting biologicalassays. Finally, we thank Dr. Imen Nouioui and Dr. Cristina Dorador for their feedback during manuscript preparation.

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This document is the Accepted Manuscript version of a Published Work that appeared in final form in the Journal of Organic Chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/abs/10.1021/acs.joc.9b02231.”
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Cite this

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title = "Downsizing Class II Lasso Peptides: Genome Mining-Guided Isolation of Huascopeptin Containing the First Gly1-Asp7 Macrocycle",

abstract = "A new lasso peptide, huascopeptin, was isolated following genome-mined discovery of a new biosynthetic gene cluster in extremotolerant Streptomyces huasconensis HST28T from Salar de Huasco, Atacama Desert, Chile. Compound 1 is a 13-residue class II lasso peptide containing a novel Gly1-Asp7 macrolactam ring, a three-residue loop, and a three-residue tail, making it the smallest lasso peptide isolated to date. The lasso structure was confirmed using NOE restraint-based molecular dynamics simulations.",

author = "Carlos Cort{\'e}s-Albayay and Jarmusch, \{Scott A\} and Franziska Trusch and Rainer Ebel and Andrews, \{Barbara A\} and Marcel Jaspars and Asenjo, \{Juan A\}",

note = "This work was financially supported by the CONICYT PFCHA/DOCTORADO BECAS CHILE/2016-21160585 fellowship and CONICYT Basal Centre Grant for the Centre for Biotechnology and Bioengineering, CeBiB (FB0001). S.A.J. thanks the University of Aberdeen for providing an Elphinstone Scholarship. We thank the Scottish High-Field NMR (SHF NMR) Centre at the University of Edinburgh for NMR experiments. We also thank Dr. Paul Herron (Strathclyde Institute of Pharmacy and Biomedical Sciences) for genome sequencing. Additionally, we thank Kirsti Helland, Marte Albrigsten, and Jeanette Andersen (University of Troms{\o} - The Arctic University of Norway) for conducting biologicalassays. Finally, we thank Dr. Imen Nouioui and Dr. Cristina Dorador for their feedback during manuscript preparation. ",

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AU - Trusch, Franziska

AU - Ebel, Rainer

AU - Andrews, Barbara A

AU - Jaspars, Marcel

AU - Asenjo, Juan A

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Downsizing Class II Lasso Peptides: Genome Mining-Guided Isolation of Huascopeptin Containing the First Gly1-Asp7 Macrocycle

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