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 (Lead / Corresponding author)

Plant Sciences

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

20 Citations (Scopus)

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

ASJC Scopus subject areas

Organic Chemistry

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10.1021/acs.joc.9b02231

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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",

year = "2020",

month = feb,

day = "7",

doi = "10.1021/acs.joc.9b02231",

language = "English",

volume = "85",

pages = "1661--1667",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Downsizing Class II Lasso Peptides

T2 - Genome Mining-Guided Isolation of Huascopeptin Containing the First Gly1-Asp7 Macrocycle

AU - Cortés-Albayay, Carlos

AU - Jarmusch, Scott A.

AU - Trusch, Franziska

AU - Ebel, Rainer

AU - Andrews, Barbara A.

AU - Jaspars, Marcel

AU - Asenjo, Juan A.

N1 - 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

PY - 2020/2/7

Y1 - 2020/2/7

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/85079095898

U2 - 10.1021/acs.joc.9b02231

DO - 10.1021/acs.joc.9b02231

M3 - Article

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AN - SCOPUS:85079095898

SN - 0022-3263

VL - 85

SP - 1661

EP - 1667

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 3

ER -

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

Abstract

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