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Fast and selective organocatalytic ring-opening polymerization by fluorinated alcohol without a cocatalyst

Organocatalysis is an important branch of catalysis for various organic transformations and materials preparation. Polymerizations promoted by organic catalysts can produce polymeric materials without any metallic residues, providing charming materials for high-value and sensitive domains such as bi...

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Autores principales: Zhao, Wei, Lv, Yanfeng, Li, Ji, Feng, Zihao, Ni, Yonghao, Hadjichristidis, Nikos
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6689068/
https://www.ncbi.nlm.nih.gov/pubmed/31399569
http://dx.doi.org/10.1038/s41467-019-11524-y
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author Zhao, Wei
Lv, Yanfeng
Li, Ji
Feng, Zihao
Ni, Yonghao
Hadjichristidis, Nikos
author_facet Zhao, Wei
Lv, Yanfeng
Li, Ji
Feng, Zihao
Ni, Yonghao
Hadjichristidis, Nikos
author_sort Zhao, Wei
collection PubMed
description Organocatalysis is an important branch of catalysis for various organic transformations and materials preparation. Polymerizations promoted by organic catalysts can produce polymeric materials without any metallic residues, providing charming materials for high-value and sensitive domains such as biomedical applications, microelectronic devices and food packaging. Herein, we describe a fluorinated alcohol based catalytic system for polypeptide synthesis via catalytic ring-opening polymerization (ROP) of α-amino acid N-carboxyanhydride (NCA), fulfilling cocatalyst free, metal free, high rate and high selectivity. During polymerization, the fluorinated alcohol catalyst forms multiple dynamic hydrogen bonds with the initiator, monomer and propagating polymer chain. These cooperative hydrogen bonding interactions activate the NCA monomers and simultaneously protect the overactive initiator/propagating polymer chain-ends, which offers the whole polymerization with high activity and selectivity. Mechanistic studies indicate a monocomponent-multifunctional catalytic mode of fluorinated alcohol. This finding provides a metal free and fast approach to access well-defined polypeptides.
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spelling pubmed-66890682019-08-12 Fast and selective organocatalytic ring-opening polymerization by fluorinated alcohol without a cocatalyst Zhao, Wei Lv, Yanfeng Li, Ji Feng, Zihao Ni, Yonghao Hadjichristidis, Nikos Nat Commun Article Organocatalysis is an important branch of catalysis for various organic transformations and materials preparation. Polymerizations promoted by organic catalysts can produce polymeric materials without any metallic residues, providing charming materials for high-value and sensitive domains such as biomedical applications, microelectronic devices and food packaging. Herein, we describe a fluorinated alcohol based catalytic system for polypeptide synthesis via catalytic ring-opening polymerization (ROP) of α-amino acid N-carboxyanhydride (NCA), fulfilling cocatalyst free, metal free, high rate and high selectivity. During polymerization, the fluorinated alcohol catalyst forms multiple dynamic hydrogen bonds with the initiator, monomer and propagating polymer chain. These cooperative hydrogen bonding interactions activate the NCA monomers and simultaneously protect the overactive initiator/propagating polymer chain-ends, which offers the whole polymerization with high activity and selectivity. Mechanistic studies indicate a monocomponent-multifunctional catalytic mode of fluorinated alcohol. This finding provides a metal free and fast approach to access well-defined polypeptides. Nature Publishing Group UK 2019-08-09 /pmc/articles/PMC6689068/ /pubmed/31399569 http://dx.doi.org/10.1038/s41467-019-11524-y Text en © The Author(s) 2019 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Article
Zhao, Wei
Lv, Yanfeng
Li, Ji
Feng, Zihao
Ni, Yonghao
Hadjichristidis, Nikos
Fast and selective organocatalytic ring-opening polymerization by fluorinated alcohol without a cocatalyst
title Fast and selective organocatalytic ring-opening polymerization by fluorinated alcohol without a cocatalyst
title_full Fast and selective organocatalytic ring-opening polymerization by fluorinated alcohol without a cocatalyst
title_fullStr Fast and selective organocatalytic ring-opening polymerization by fluorinated alcohol without a cocatalyst
title_full_unstemmed Fast and selective organocatalytic ring-opening polymerization by fluorinated alcohol without a cocatalyst
title_short Fast and selective organocatalytic ring-opening polymerization by fluorinated alcohol without a cocatalyst
title_sort fast and selective organocatalytic ring-opening polymerization by fluorinated alcohol without a cocatalyst
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6689068/
https://www.ncbi.nlm.nih.gov/pubmed/31399569
http://dx.doi.org/10.1038/s41467-019-11524-y
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