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Cyclisation mechanisms in the biosynthesis of ribosomally synthesised and post-translationally modified peptides

Ribosomally synthesised and post-translationally modified peptides (RiPPs) are a large class of natural products that are remarkably chemically diverse given an intrinsic requirement to be assembled from proteinogenic amino acids. The vast chemical space occupied by RiPPs means that they possess a w...

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Autor principal: Truman, Andrew W
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4979651/
https://www.ncbi.nlm.nih.gov/pubmed/27559376
http://dx.doi.org/10.3762/bjoc.12.120
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author Truman, Andrew W
author_facet Truman, Andrew W
author_sort Truman, Andrew W
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description Ribosomally synthesised and post-translationally modified peptides (RiPPs) are a large class of natural products that are remarkably chemically diverse given an intrinsic requirement to be assembled from proteinogenic amino acids. The vast chemical space occupied by RiPPs means that they possess a wide variety of biological activities, and the class includes antibiotics, co-factors, signalling molecules, anticancer and anti-HIV compounds, and toxins. A considerable amount of RiPP chemical diversity is generated from cyclisation reactions, and the current mechanistic understanding of these reactions will be discussed here. These cyclisations involve a diverse array of chemical reactions, including 1,4-nucleophilic additions, [4 + 2] cycloadditions, ATP-dependent heterocyclisation to form thiazolines or oxazolines, and radical-mediated reactions between unactivated carbons. Future prospects for RiPP pathway discovery and characterisation will also be highlighted.
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spelling pubmed-49796512016-08-24 Cyclisation mechanisms in the biosynthesis of ribosomally synthesised and post-translationally modified peptides Truman, Andrew W Beilstein J Org Chem Review Ribosomally synthesised and post-translationally modified peptides (RiPPs) are a large class of natural products that are remarkably chemically diverse given an intrinsic requirement to be assembled from proteinogenic amino acids. The vast chemical space occupied by RiPPs means that they possess a wide variety of biological activities, and the class includes antibiotics, co-factors, signalling molecules, anticancer and anti-HIV compounds, and toxins. A considerable amount of RiPP chemical diversity is generated from cyclisation reactions, and the current mechanistic understanding of these reactions will be discussed here. These cyclisations involve a diverse array of chemical reactions, including 1,4-nucleophilic additions, [4 + 2] cycloadditions, ATP-dependent heterocyclisation to form thiazolines or oxazolines, and radical-mediated reactions between unactivated carbons. Future prospects for RiPP pathway discovery and characterisation will also be highlighted. Beilstein-Institut 2016-06-20 /pmc/articles/PMC4979651/ /pubmed/27559376 http://dx.doi.org/10.3762/bjoc.12.120 Text en Copyright © 2016, Truman https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Review
Truman, Andrew W
Cyclisation mechanisms in the biosynthesis of ribosomally synthesised and post-translationally modified peptides
title Cyclisation mechanisms in the biosynthesis of ribosomally synthesised and post-translationally modified peptides
title_full Cyclisation mechanisms in the biosynthesis of ribosomally synthesised and post-translationally modified peptides
title_fullStr Cyclisation mechanisms in the biosynthesis of ribosomally synthesised and post-translationally modified peptides
title_full_unstemmed Cyclisation mechanisms in the biosynthesis of ribosomally synthesised and post-translationally modified peptides
title_short Cyclisation mechanisms in the biosynthesis of ribosomally synthesised and post-translationally modified peptides
title_sort cyclisation mechanisms in the biosynthesis of ribosomally synthesised and post-translationally modified peptides
topic Review
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4979651/
https://www.ncbi.nlm.nih.gov/pubmed/27559376
http://dx.doi.org/10.3762/bjoc.12.120
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