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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Published inNature communications Vol. 10; no. 1; pp. 3590 - 11
Main Authors Zhao, Wei, Lv, Yanfeng, Li, Ji, Feng, Zihao, Ni, Yonghao, Hadjichristidis, Nikos
Format Journal Article
LanguageEnglish
Published London Nature Publishing Group UK 09.08.2019
Nature Publishing Group
Nature Portfolio
Subjects
140/131
140/58
147/135
639/638/549/941
639/638/77/889
Alcohol
Alcohols
Alcohols - chemistry
Amino acids
Amino Acids - chemistry
Biomedical materials
Catalysis
Catalysts
Chains (polymeric)
Chemical synthesis
Chemistry Techniques, Synthetic - methods
Domains
Fluorination
Food packaging
Halogenation
Humanities and Social Sciences
Hydrogen bonding
Hydrogen bonds
Monomers
multidisciplinary
Peptides - chemical synthesis
Polymerization
Polymers
Polypeptides
Propagation (polymerization)
Ring opening polymerization
Science
Science (multidisciplinary)
Selectivity
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Abstract 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. Polymerizations promoted by organic catalysts can produce polymeric materials without any metallic residues contamination. Here the authors show a fluorinated alcohol based catalytic system for polypeptide synthesis from α-amino acid N -carboxyanhydride, fulfilling cocatalyst and metal free conditions with high rate and selectivity.
AbstractList 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.
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. Polymerizations promoted by organic catalysts can produce polymeric materials without any metallic residues contamination. Here the authors show a fluorinated alcohol based catalytic system for polypeptide synthesis from α-amino acid N -carboxyanhydride, fulfilling cocatalyst and metal free conditions with high rate and selectivity.
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.
Polymerizations promoted by organic catalysts can produce polymeric materials without any metallic residues contamination. Here the authors show a fluorinated alcohol based catalytic system for polypeptide synthesis from α-amino acid N-carboxyanhydride, fulfilling cocatalyst and metal free conditions with high rate and selectivity.
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.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.
ArticleNumber 3590
Author Zhao, Wei
Ni, Yonghao
Hadjichristidis, Nikos
Li, Ji
Feng, Zihao
Lv, Yanfeng
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  organization: College of Bioresources Chemical and Materials Engineering, Shaanxi University of Science and Technology
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  surname: Lv
  fullname: Lv, Yanfeng
  organization: College of Bioresources Chemical and Materials Engineering, Shaanxi University of Science and Technology
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  surname: Li
  fullname: Li, Ji
  organization: College of Bioresources Chemical and Materials Engineering, Shaanxi University of Science and Technology
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  surname: Feng
  fullname: Feng, Zihao
  organization: College of Bioresources Chemical and Materials Engineering, Shaanxi University of Science and Technology
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  surname: Hadjichristidis
  fullname: Hadjichristidis, Nikos
  organization: KAUST Catalysis Center, Polymer Synthesis Laboratory, Physical Sciences and Engineering Division, King Abdullah University of Science and Technology (KAUST)
BackLink https://www.ncbi.nlm.nih.gov/pubmed/31399569$$D View this record in MEDLINE/PubMed
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SSID ssj0000391844
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Snippet Organocatalysis is an important branch of catalysis for various organic transformations and materials preparation. Polymerizations promoted by organic...
Polymerizations promoted by organic catalysts can produce polymeric materials without any metallic residues contamination. Here the authors show a fluorinated...
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StartPage 3590
SubjectTerms 140/131
140/58
147/135
639/638/549/941
639/638/77/889
Alcohol
Alcohols
Alcohols - chemistry
Amino acids
Amino Acids - chemistry
Biomedical materials
Catalysis
Catalysts
Chains (polymeric)
Chemical synthesis
Chemistry Techniques, Synthetic - methods
Domains
Fluorination
Food packaging
Halogenation
Humanities and Social Sciences
Hydrogen bonding
Hydrogen bonds
Monomers
multidisciplinary
Peptides - chemical synthesis
Polymerization
Polymers
Polypeptides
Propagation (polymerization)
Ring opening polymerization
Science
Science (multidisciplinary)
Selectivity
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Title Fast and selective organocatalytic ring-opening polymerization by fluorinated alcohol without a cocatalyst
URI https://link.springer.com/article/10.1038/s41467-019-11524-y
https://www.ncbi.nlm.nih.gov/pubmed/31399569
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https://www.proquest.com/docview/2271850608
https://pubmed.ncbi.nlm.nih.gov/PMC6689068
https://doaj.org/article/4ff90e3c90ae47269ae55188623ede3d
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