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Total synthesis of micrococcin P1 and thiocillin I enabled by Mo(vi) catalyst
Thiopeptides are a class of potent antibiotics with promising therapeutic potential. We developed a novel Mo(vi)-oxide/picolinic acid catalyst for the cyclodehydration of cysteine peptides to form thiazoline heterocycles. With this powerful tool in hand, we completed the total syntheses of two repre...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Royal Society of Chemistry
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6383332/ https://www.ncbi.nlm.nih.gov/pubmed/30881626 http://dx.doi.org/10.1039/c8sc04885a |
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author | Akasapu, Siddhartha Hinds, Aaron B. Powell, Wyatt C. Walczak, Maciej A. |
author_facet | Akasapu, Siddhartha Hinds, Aaron B. Powell, Wyatt C. Walczak, Maciej A. |
author_sort | Akasapu, Siddhartha |
collection | PubMed |
description | Thiopeptides are a class of potent antibiotics with promising therapeutic potential. We developed a novel Mo(vi)-oxide/picolinic acid catalyst for the cyclodehydration of cysteine peptides to form thiazoline heterocycles. With this powerful tool in hand, we completed the total syntheses of two representative thiopeptide antibiotics: micrococcin P1 and thiocillin I. These two concise syntheses (15 steps, longest linear sequence) feature a C–H activation strategy to install the trisubstituted pyridine core and thiazole groups. The synthetic material displays promising antimicrobial properties measured against a series of Gram-positive bacteria. |
format | Online Article Text |
id | pubmed-6383332 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-63833322019-03-15 Total synthesis of micrococcin P1 and thiocillin I enabled by Mo(vi) catalyst Akasapu, Siddhartha Hinds, Aaron B. Powell, Wyatt C. Walczak, Maciej A. Chem Sci Chemistry Thiopeptides are a class of potent antibiotics with promising therapeutic potential. We developed a novel Mo(vi)-oxide/picolinic acid catalyst for the cyclodehydration of cysteine peptides to form thiazoline heterocycles. With this powerful tool in hand, we completed the total syntheses of two representative thiopeptide antibiotics: micrococcin P1 and thiocillin I. These two concise syntheses (15 steps, longest linear sequence) feature a C–H activation strategy to install the trisubstituted pyridine core and thiazole groups. The synthetic material displays promising antimicrobial properties measured against a series of Gram-positive bacteria. Royal Society of Chemistry 2018-12-03 /pmc/articles/PMC6383332/ /pubmed/30881626 http://dx.doi.org/10.1039/c8sc04885a Text en This journal is © The Royal Society of Chemistry 2019 http://creativecommons.org/licenses/by-nc/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0) |
spellingShingle | Chemistry Akasapu, Siddhartha Hinds, Aaron B. Powell, Wyatt C. Walczak, Maciej A. Total synthesis of micrococcin P1 and thiocillin I enabled by Mo(vi) catalyst |
title | Total synthesis of micrococcin P1 and thiocillin I enabled by Mo(vi) catalyst
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title_full | Total synthesis of micrococcin P1 and thiocillin I enabled by Mo(vi) catalyst
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title_fullStr | Total synthesis of micrococcin P1 and thiocillin I enabled by Mo(vi) catalyst
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title_full_unstemmed | Total synthesis of micrococcin P1 and thiocillin I enabled by Mo(vi) catalyst
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title_short | Total synthesis of micrococcin P1 and thiocillin I enabled by Mo(vi) catalyst
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title_sort | total synthesis of micrococcin p1 and thiocillin i enabled by mo(vi) catalyst |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6383332/ https://www.ncbi.nlm.nih.gov/pubmed/30881626 http://dx.doi.org/10.1039/c8sc04885a |
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