Triazine‐Based Sequence‐Defined Polymers with Side‐Chain Diversity and Backbone–Backbone Interaction Motifs

Grate, Jay W.; Mo, Kai‐For; Daily, Michael D.

doi:10.1002/anie.201509864

Title: Triazine‐Based Sequence‐Defined Polymers with Side‐Chain Diversity and Backbone–Backbone Interaction Motifs

Abstract

Sequence control in polymers, well-known in nature, encodes structure and functionality. Here we introduce a new architecture, based on the nucleophilic aromatic substitution chemistry of cyanuric chloride, that creates a new class of sequence-defined polymers dubbed TZPs. Proof of concept is demonstrated with two synthesized hexamers, having neutral and ionizable side chains. Molecular dynamics simulations show backbone–backbone interactions, including H-bonding motifs and pi–pi interactions. This architecture is arguably biomimetic while differing from sequence-defined polymers having peptide bonds. In conclusion, the synthetic methodology supports the structural diversity of side chains known in peptides, as well as backbone–backbone hydrogen-bonding motifs, and will thus enable new macromolecules and materials with useful functions.

Authors:

^[1]; Mo, Kai‐For ^[1]; Daily, Michael D. ^[1]

Pacific Northwest National Laboratory P.O. Box 999 Richland WA 99352 USA

Publication Date:: Wed Feb 10 00:00:00 EST 2016

Research Org.:: Pacific Northwest National Laboratory (PNNL), Richland, WA (United States)

Sponsoring Org.:: USDOE

OSTI Identifier:: 1241920

Alternate Identifier(s):: OSTI ID: 1241921; OSTI ID: 1328710; OSTI ID: 1337231

Report Number(s):: PNNL-SA-114408
Journal ID: ISSN 1433-7851

Grant/Contract Number:: AC05-76RL01830

Resource Type:: Published Article

Journal Name:: Angewandte Chemie (International Edition)

Additional Journal Information:: Journal Name: Angewandte Chemie (International Edition) Journal Volume: 55 Journal Issue: 12; Journal ID: ISSN 1433-7851

Publisher:: Wiley Blackwell (John Wiley & Sons)

Country of Publication:: Germany

Language:: English

Subject:: 36 MATERIALS SCIENCE; polymer; material

Citation Formats


                    Grate, Jay W., Mo, Kai‐For, and Daily, Michael D. Triazine‐Based Sequence‐Defined Polymers with Side‐Chain Diversity and Backbone–Backbone Interaction Motifs.  Germany: N. p., 2016. 
Web.  doi:10.1002/anie.201509864.

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                    Grate, Jay W., Mo, Kai‐For, & Daily, Michael D. Triazine‐Based Sequence‐Defined Polymers with Side‐Chain Diversity and Backbone–Backbone Interaction Motifs.  Germany.  https://doi.org/10.1002/anie.201509864

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                    Grate, Jay W., Mo, Kai‐For, and Daily, Michael D. Wed .  
"Triazine‐Based Sequence‐Defined Polymers with Side‐Chain Diversity and Backbone–Backbone Interaction Motifs".  Germany.  https://doi.org/10.1002/anie.201509864.

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@article{osti_1241920,

  title        = {Triazine‐Based Sequence‐Defined Polymers with Side‐Chain Diversity and Backbone–Backbone Interaction Motifs},

  author       = {Grate, Jay W. and Mo, Kai‐For and Daily, Michael D.},

  abstractNote = {Sequence control in polymers, well-known in nature, encodes structure and functionality. Here we introduce a new architecture, based on the nucleophilic aromatic substitution chemistry of cyanuric chloride, that creates a new class of sequence-defined polymers dubbed TZPs. Proof of concept is demonstrated with two synthesized hexamers, having neutral and ionizable side chains. Molecular dynamics simulations show backbone–backbone interactions, including H-bonding motifs and pi–pi interactions. This architecture is arguably biomimetic while differing from sequence-defined polymers having peptide bonds. In conclusion, the synthetic methodology supports the structural diversity of side chains known in peptides, as well as backbone–backbone hydrogen-bonding motifs, and will thus enable new macromolecules and materials with useful functions.},

  doi          = {10.1002/anie.201509864},

  journal      = {Angewandte Chemie (International Edition)},

  number       = 12,

  volume       = 55,

  place        = {Germany},

  year         = {Wed Feb 10 00:00:00 EST 2016},

  month        = {Wed Feb 10 00:00:00 EST 2016}

}

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Title: Triazine‐Based Sequence‐Defined Polymers with Side‐Chain Diversity and Backbone–Backbone Interaction Motifs

Abstract

Citation Formats

Synthesis of Monodisperse Sequence-Defined Polymers Using Protecting-Group-Free Iterative Strategies journal, May 2015

Sequence Control in Polymer Chemistry through the Passerini Three-Component Reaction journal, December 2013

Synthesis and conformational studies of pseudopeptides containing an unsymmetrical triazine scaffold journal, May 2008

Design and synthesis of digitally encoded polymers that can be decoded and erased journal, May 2015

Sequence-Defined Polymers via Orthogonal Allyl Acrylamide Building Blocks journal, September 2014

Preparation of Information-Containing Macromolecules by Ligation of Dyad-Encoded Oligomers journal, July 2015

Sequence-Controlled Polymers journal, August 2013

Peptoid Polymers: A Highly Designable Bioinspired Material journal, May 2013

Photo-induced sequence defined macromolecules via hetero bifunctional synthons journal, January 2015

Liquid-Phase Synthesis of Block Copolymers Containing Sequence-Ordered Segments journal, July 2009

Foldamers: A Manifesto journal, April 1998

Self-Complementarity Achieved through Quadruple Hydrogen Bonding journal, February 1998

Sequence Matters: Modulating Electronic and Optical Properties of Conjugated Oligomers via Tailored Sequence journal, February 2013

Non-covalent polymer assembly using arrays of hydrogen-bonds journal, January 2007

“Lesen” von Polymeren: Die Sequenzierung natürlicher und synthetischer Makromoleküle journal, October 2014

Sequentially Hetero-functional, Topological Polymers by Step-growth Thiol-yne Approach journal, March 2014

A Field Guide to Foldamers journal, December 2001

Automatic atom type and bond type perception in molecular mechanical calculations journal, October 2006

Durch vier Wasserstoffbrückenbindungen vermittelte Selbstkomplementarität journal, January 1998

Multifunctionalized Sequence-Defined Oligomers from a Single Building Block journal, October 2013

Efficient method for the preparation of peptoids [oligo(N-substituted glycines)] by submonomer solid-phase synthesis journal, December 1992

Helicity-Encoded Molecular Strands: Efficient Access by the Hydrazone Route and Structural Features journal, May 2003

Refolding Foldamers: Triazene-Arylene Oligomers That Change Shape with Chemical Stimuli journal, September 2007

Synthesis of sequence-ordered polymers via sequential addition of monomers in one pot journal, January 2013

Pseudo porphyrinyl amino acids based on 1,3,5-triazine scaffold: new tools for the synthesis of peptidic porphyrins journal, June 2011

Sequenzkontrolle in der Polymerchemie mithilfe der Passerini- Dreikomponentenreaktion journal, December 2013

Periodic Incorporation of Pendant Hydroxyl Groups in Repeating Sequence PLGA Copolymers journal, November 2010

GROMACS 4.5: a high-throughput and highly parallel open source molecular simulation toolkit journal, February 2013

Solid-Phase Supported Polymer Synthesis of Sequence-Defined, Multifunctional Poly(amidoamines) journal, April 2006

Synthetic foldamers journal, January 2011

Beyond de novo protein design — de novo design of non-natural folded oligomers journal, August 2004

Duplex Oligomers Defined via Covalent Casting of a One-Dimensional Hydrogen-Bonding Motif journal, May 2002

Reading Polymers: Sequencing of Natural and Synthetic Macromolecules journal, October 2014

Development and testing of a general amber force field journal, January 2004

Synthesis, structural investigation and computational modelling of water-binding aquafoldamers journal, January 2012

Synthesis of Molecularly Encoded Oligomers Using a Chemoselective “AB + CD” Iterative Approach journal, December 2013

ACPYPE - AnteChamber PYthon Parser interfacE journal, January 2012

Convergent synthesis of digitally-encoded poly(alkoxyamine amide)s journal, January 2015

Recent applications of 2,4,6-trichloro-1,3,5-triazine and its derivatives in organic synthesis journal, October 2006

Triazinyl-Amino Acids, New Building Blocks for Pseudopeptides journal, January 2002

Multifunctionalized Sequence-Defined Oligomers from a Single Building Block journal, October 2013

A General Approach to Sequence-Controlled Polymers Using Macrocyclic Ring Opening Metathesis Polymerization journal, June 2015

Synthesis of Monodisperse Sequence-Defined Polymers Using Protecting-Group-Free Iterative Strategies
journal, May 2015

Sequence Control in Polymer Chemistry through the Passerini Three-Component Reaction
journal, December 2013

Synthesis and conformational studies of pseudopeptides containing an unsymmetrical triazine scaffold
journal, May 2008

Design and synthesis of digitally encoded polymers that can be decoded and erased
journal, May 2015

Sequence-Defined Polymers via Orthogonal Allyl Acrylamide Building Blocks
journal, September 2014

Preparation of Information-Containing Macromolecules by Ligation of Dyad-Encoded Oligomers
journal, July 2015

Sequence-Controlled Polymers
journal, August 2013

Peptoid Polymers: A Highly Designable Bioinspired Material
journal, May 2013

Photo-induced sequence defined macromolecules via hetero bifunctional synthons
journal, January 2015

Liquid-Phase Synthesis of Block Copolymers Containing Sequence-Ordered Segments
journal, July 2009

Foldamers: A Manifesto
journal, April 1998

Self-Complementarity Achieved through Quadruple Hydrogen Bonding
journal, February 1998

Sequence Matters: Modulating Electronic and Optical Properties of Conjugated Oligomers via Tailored Sequence
journal, February 2013

Non-covalent polymer assembly using arrays of hydrogen-bonds
journal, January 2007

“Lesen” von Polymeren: Die Sequenzierung natürlicher und synthetischer Makromoleküle
journal, October 2014

Sequentially Hetero-functional, Topological Polymers by Step-growth Thiol-yne Approach
journal, March 2014

A Field Guide to Foldamers
journal, December 2001

Automatic atom type and bond type perception in molecular mechanical calculations
journal, October 2006

Durch vier Wasserstoffbrückenbindungen vermittelte Selbstkomplementarität
journal, January 1998

Multifunctionalized Sequence-Defined Oligomers from a Single Building Block
journal, October 2013

Efficient method for the preparation of peptoids [oligo(N-substituted glycines)] by submonomer solid-phase synthesis
journal, December 1992

Helicity-Encoded Molecular Strands: Efficient Access by the Hydrazone Route and Structural Features
journal, May 2003

Refolding Foldamers: Triazene-Arylene Oligomers That Change Shape with Chemical Stimuli
journal, September 2007

Synthesis of sequence-ordered polymers via sequential addition of monomers in one pot
journal, January 2013

Pseudo porphyrinyl amino acids based on 1,3,5-triazine scaffold: new tools for the synthesis of peptidic porphyrins
journal, June 2011

Sequenzkontrolle in der Polymerchemie mithilfe der Passerini- Dreikomponentenreaktion
journal, December 2013

Periodic Incorporation of Pendant Hydroxyl Groups in Repeating Sequence PLGA Copolymers
journal, November 2010

GROMACS 4.5: a high-throughput and highly parallel open source molecular simulation toolkit
journal, February 2013

Solid-Phase Supported Polymer Synthesis of Sequence-Defined, Multifunctional Poly(amidoamines)
journal, April 2006

Synthetic foldamers
journal, January 2011

Beyond de novo protein design — de novo design of non-natural folded oligomers
journal, August 2004

Duplex Oligomers Defined via Covalent Casting of a One-Dimensional Hydrogen-Bonding Motif
journal, May 2002

Reading Polymers: Sequencing of Natural and Synthetic Macromolecules
journal, October 2014

Development and testing of a general amber force field
journal, January 2004

Synthesis, structural investigation and computational modelling of water-binding aquafoldamers
journal, January 2012

Synthesis of Molecularly Encoded Oligomers Using a Chemoselective “AB + CD” Iterative Approach
journal, December 2013

ACPYPE - AnteChamber PYthon Parser interfacE
journal, January 2012

Convergent synthesis of digitally-encoded poly(alkoxyamine amide)s
journal, January 2015

Recent applications of 2,4,6-trichloro-1,3,5-triazine and its derivatives in organic synthesis
journal, October 2006

Triazinyl-Amino Acids, New Building Blocks for Pseudopeptides
journal, January 2002

Multifunctionalized Sequence-Defined Oligomers from a Single Building Block
journal, October 2013

A General Approach to Sequence-Controlled Polymers Using Macrocyclic Ring Opening Metathesis Polymerization
journal, June 2015