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A Concise Synthetic Strategy Towards the Novel Calcium-dependent Lipopeptide Antibiotic, Malacidin A and Analogues
Malacidin A is a novel calcium-dependent lipopeptide antibiotic with excellent activity against Gram-positive pathogens. Herein, a concise and robust synthetic route toward malacidin A is reported, employing 9-fluorenylmethoxycarbonyl solid-phase peptide synthesis of a linear precursor, including la...
Autores principales: | , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Frontiers Media S.A.
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8372822/ https://www.ncbi.nlm.nih.gov/pubmed/34422759 http://dx.doi.org/10.3389/fchem.2021.687875 |
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author | Kovalenko, Nadiia Howard, Georgina K. Swain, Jonathan A. Hermant, Yann Cameron, Alan J. Cook, Gregory M. Ferguson, Scott A. Stubbing, Louise A. Harris, Paul W. R. Brimble, Margaret A. |
author_facet | Kovalenko, Nadiia Howard, Georgina K. Swain, Jonathan A. Hermant, Yann Cameron, Alan J. Cook, Gregory M. Ferguson, Scott A. Stubbing, Louise A. Harris, Paul W. R. Brimble, Margaret A. |
author_sort | Kovalenko, Nadiia |
collection | PubMed |
description | Malacidin A is a novel calcium-dependent lipopeptide antibiotic with excellent activity against Gram-positive pathogens. Herein, a concise and robust synthetic route toward malacidin A is reported, employing 9-fluorenylmethoxycarbonyl solid-phase peptide synthesis of a linear precursor, including late-stage incorporation of the lipid tail, followed by solution-phase cyclization. The versatility of this synthetic strategy was further demonstrated by synthesis of a diastereomeric variant of malacidin A and a small library of simplified analogues with variation of the lipid moiety. |
format | Online Article Text |
id | pubmed-8372822 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | Frontiers Media S.A. |
record_format | MEDLINE/PubMed |
spelling | pubmed-83728222021-08-19 A Concise Synthetic Strategy Towards the Novel Calcium-dependent Lipopeptide Antibiotic, Malacidin A and Analogues Kovalenko, Nadiia Howard, Georgina K. Swain, Jonathan A. Hermant, Yann Cameron, Alan J. Cook, Gregory M. Ferguson, Scott A. Stubbing, Louise A. Harris, Paul W. R. Brimble, Margaret A. Front Chem Chemistry Malacidin A is a novel calcium-dependent lipopeptide antibiotic with excellent activity against Gram-positive pathogens. Herein, a concise and robust synthetic route toward malacidin A is reported, employing 9-fluorenylmethoxycarbonyl solid-phase peptide synthesis of a linear precursor, including late-stage incorporation of the lipid tail, followed by solution-phase cyclization. The versatility of this synthetic strategy was further demonstrated by synthesis of a diastereomeric variant of malacidin A and a small library of simplified analogues with variation of the lipid moiety. Frontiers Media S.A. 2021-08-04 /pmc/articles/PMC8372822/ /pubmed/34422759 http://dx.doi.org/10.3389/fchem.2021.687875 Text en Copyright © 2021 Kovalenko, Howard, Swain, Hermant, Cameron, Cook, Ferguson, Stubbing, Harris and Brimble. https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms. |
spellingShingle | Chemistry Kovalenko, Nadiia Howard, Georgina K. Swain, Jonathan A. Hermant, Yann Cameron, Alan J. Cook, Gregory M. Ferguson, Scott A. Stubbing, Louise A. Harris, Paul W. R. Brimble, Margaret A. A Concise Synthetic Strategy Towards the Novel Calcium-dependent Lipopeptide Antibiotic, Malacidin A and Analogues |
title | A Concise Synthetic Strategy Towards the Novel Calcium-dependent Lipopeptide Antibiotic, Malacidin A and Analogues |
title_full | A Concise Synthetic Strategy Towards the Novel Calcium-dependent Lipopeptide Antibiotic, Malacidin A and Analogues |
title_fullStr | A Concise Synthetic Strategy Towards the Novel Calcium-dependent Lipopeptide Antibiotic, Malacidin A and Analogues |
title_full_unstemmed | A Concise Synthetic Strategy Towards the Novel Calcium-dependent Lipopeptide Antibiotic, Malacidin A and Analogues |
title_short | A Concise Synthetic Strategy Towards the Novel Calcium-dependent Lipopeptide Antibiotic, Malacidin A and Analogues |
title_sort | concise synthetic strategy towards the novel calcium-dependent lipopeptide antibiotic, malacidin a and analogues |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8372822/ https://www.ncbi.nlm.nih.gov/pubmed/34422759 http://dx.doi.org/10.3389/fchem.2021.687875 |
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