Cargando…
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...
Autores principales: | , , , , , |
---|---|
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 |
_version_ | 1783442981257216000 |
---|---|
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. |
format | Online Article Text |
id | pubmed-6689068 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | Nature Publishing Group UK |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT zhaowei fastandselectiveorganocatalyticringopeningpolymerizationbyfluorinatedalcoholwithoutacocatalyst AT lvyanfeng fastandselectiveorganocatalyticringopeningpolymerizationbyfluorinatedalcoholwithoutacocatalyst AT liji fastandselectiveorganocatalyticringopeningpolymerizationbyfluorinatedalcoholwithoutacocatalyst AT fengzihao fastandselectiveorganocatalyticringopeningpolymerizationbyfluorinatedalcoholwithoutacocatalyst AT niyonghao fastandselectiveorganocatalyticringopeningpolymerizationbyfluorinatedalcoholwithoutacocatalyst AT hadjichristidisnikos fastandselectiveorganocatalyticringopeningpolymerizationbyfluorinatedalcoholwithoutacocatalyst |