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/ange.201509864

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

Journal Article · Wed Feb 10 00:00:00 EST 2016 · Angewandte Chemie

DOI:https://doi.org/10.1002/ange.201509864· OSTI ID:1241918

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

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

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. 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.

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Sponsoring Organization:: USDOE

OSTI ID:: 1241918

Alternate ID(s):: OSTI ID: 1241919

Journal Information:: Angewandte Chemie, Journal Name: Angewandte Chemie Vol. 128 Journal Issue: 12; ISSN 0044-8249

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

References (42)

Synthesis of Monodisperse Sequence-Defined Polymers Using Protecting-Group-Free Iterative Strategies Trinh, Thanh Tam; Laure, Chloé; Lutz, Jean-François Macromolecular Chemistry and Physics, Vol. 216, Issue 14 https://doi.org/10.1002/macp.201500072	journal	May 2015
Sequence Control in Polymer Chemistry through the Passerini Three-Component Reaction Solleder, Susanne C.; Meier, Michael A. R. Angewandte Chemie International Edition, Vol. 53, Issue 3 https://doi.org/10.1002/anie.201308960	journal	December 2013
Synthesis and conformational studies of pseudopeptides containing an unsymmetrical triazine scaffold Bourguet, Erika; Correia, Isabelle; Dorgeret, Bertrand Journal of Peptide Science, Vol. 14, Issue 5 https://doi.org/10.1002/psc.944	journal	May 2008
Design and synthesis of digitally encoded polymers that can be decoded and erased Roy, Raj Kumar; Meszynska, Anna; Laure, Chloé Nature Communications, Vol. 6, Issue 1 https://doi.org/10.1038/ncomms8237	journal	May 2015
Sequence-Defined Polymers via Orthogonal Allyl Acrylamide Building Blocks Porel, Mintu; Alabi, Christopher A. Journal of the American Chemical Society, Vol. 136, Issue 38 https://doi.org/10.1021/ja507262t	journal	September 2014
Preparation of Information-Containing Macromolecules by Ligation of Dyad-Encoded Oligomers Trinh, Thanh Tam; Oswald, Laurence; Chan-Seng, Delphine Chemistry - A European Journal, Vol. 21, Issue 34 https://doi.org/10.1002/chem.201502414	journal	July 2015
Sequence-Controlled Polymers Lutz, J. -F.; Ouchi, M.; Liu, D. R. Science, Vol. 341, Issue 6146 https://doi.org/10.1126/science.1238149	journal	August 2013
Peptoid Polymers: A Highly Designable Bioinspired Material Sun, Jing; Zuckermann, Ronald N. ACS Nano, Vol. 7, Issue 6 https://doi.org/10.1021/nn4015714	journal	May 2013
Photo-induced sequence defined macromolecules via hetero bifunctional synthons Zydziak, Nicolas; Feist, Florian; Huber, Birgit Chemical Communications, Vol. 51, Issue 10 https://doi.org/10.1039/C4CC08756A	journal	January 2015
Liquid-Phase Synthesis of Block Copolymers Containing Sequence-Ordered Segments Pfeifer, Sebastian; Zarafshani, Zoya; Badi, Nezha Journal of the American Chemical Society, Vol. 131, Issue 26 https://doi.org/10.1021/ja903635y	journal	July 2009
Foldamers: A Manifesto Gellman, Samuel H. Accounts of Chemical Research, Vol. 31, Issue 4 https://doi.org/10.1021/ar960298r	journal	April 1998
Self-Complementarity Achieved through Quadruple Hydrogen Bonding Beijer, Felix H.; Kooijman, Huub; Spek, Anthony L. Angewandte Chemie International Edition, Vol. 37, Issue 1-2, p. 75-78 https://doi.org/10.1002/(SICI)1521-3773(19980202)37:1/2<75::AID-ANIE75>3.0.CO;2-R	journal	February 1998
Sequence Matters: Modulating Electronic and Optical Properties of Conjugated Oligomers via Tailored Sequence Norris, Benjamin N.; Zhang, Shaopeng; Campbell, Casey M. Macromolecules, Vol. 46, Issue 4 https://doi.org/10.1021/ma400123r	journal	February 2013
Non-covalent polymer assembly using arrays of hydrogen-bonds Wilson, Andrew J. Soft Matter, Vol. 3, Issue 4 https://doi.org/10.1039/b612566b	journal	January 2007
“Lesen” von Polymeren: Die Sequenzierung natürlicher und synthetischer Makromoleküle Mutlu, Hatice; Lutz, Jean-François Angewandte Chemie, Vol. 126, Issue 48 https://doi.org/10.1002/ange.201406766	journal	October 2014
Sequentially Hetero-functional, Topological Polymers by Step-growth Thiol-yne Approach Han, Jin; Zheng, Yaochen; Zhao, Bo Scientific Reports, Vol. 4, Issue 1 https://doi.org/10.1038/srep04387	journal	March 2014
A Field Guide to Foldamers Hill, David J.; Mio, Matthew J.; Prince, Ryan B. Chemical Reviews, Vol. 101, Issue 12 https://doi.org/10.1021/cr990120t	journal	December 2001
Automatic atom type and bond type perception in molecular mechanical calculations Wang, Junmei; Wang, Wei; Kollman, Peter A. Journal of Molecular Graphics and Modelling, Vol. 25, Issue 2 https://doi.org/10.1016/j.jmgm.2005.12.005	journal	October 2006
Durch vier Wasserstoffbrückenbindungen vermittelte Selbstkomplementarität Beijer, Felix H.; Kooijman, Huub; Spek, Anthony L. Angewandte Chemie, Vol. 110, Issue 1-2 https://doi.org/10.1002/(SICI)1521-3757(19980116)110:1/2<79::AID-ANGE79>3.0.CO;2-V	journal	January 1998
Multifunctionalized Sequence-Defined Oligomers from a Single Building Block Espeel, Pieter; Carrette, Lieselot L. G.; Bury, Katarzyna Angewandte Chemie, Vol. 125, Issue 50 https://doi.org/10.1002/ange.201307439	journal	October 2013
Efficient method for the preparation of peptoids [oligo(N-substituted glycines)] by submonomer solid-phase synthesis Zuckermann, Ronald N.; Kerr, Janice M.; Kent, Stephen B. H. Journal of the American Chemical Society, Vol. 114, Issue 26 https://doi.org/10.1021/ja00052a076	journal	December 1992
Helicity-Encoded Molecular Strands: Efficient Access by the Hydrazone Route and Structural Features Schmitt, Jean-Louis; Stadler, Adrian-Mihail; Kyritsakas, Nathalie Helvetica Chimica Acta, Vol. 86, Issue 5, p. 1598-1624 https://doi.org/10.1002/hlca.200390137	journal	May 2003
Refolding Foldamers: Triazene-Arylene Oligomers That Change Shape with Chemical Stimuli Liu, Simin; Zavalij, Peter Y.; Lam, Yiu-Fai Journal of the American Chemical Society, Vol. 129, Issue 36, p. 11232-11241 https://doi.org/10.1021/ja073320s	journal	September 2007
Synthesis of sequence-ordered polymers via sequential addition of monomers in one pot Yan, Jun-Jie; Wang, Di; Wu, De-Cheng Chemical Communications, Vol. 49, Issue 54 https://doi.org/10.1039/c3cc42483a	journal	January 2013
Pseudo porphyrinyl amino acids based on 1,3,5-triazine scaffold: new tools for the synthesis of peptidic porphyrins Chaleix, Vincent; Sol, Vincent; Krausz, Pierre Tetrahedron Letters, Vol. 52, Issue 23, p. 2977-2979 https://doi.org/10.1016/j.tetlet.2011.03.136	journal	June 2011
Sequenzkontrolle in der Polymerchemie mithilfe der Passerini- Dreikomponentenreaktion Solleder, Susanne C.; Meier, Michael A. R. Angewandte Chemie, Vol. 126, Issue 3 https://doi.org/10.1002/ange.201308960	journal	December 2013
Periodic Incorporation of Pendant Hydroxyl Groups in Repeating Sequence PLGA Copolymers Stayshich, Ryan M.; Weiss, Ryan M.; Li, Jian Macromolecular Rapid Communications, Vol. 32, Issue 2 https://doi.org/10.1002/marc.201000608	journal	November 2010
GROMACS 4.5: a high-throughput and highly parallel open source molecular simulation toolkit Pronk, Sander; Páll, Szilárd; Schulz, Roland Bioinformatics, Vol. 29, Issue 7 https://doi.org/10.1093/bioinformatics/btt055	journal	February 2013
Solid-Phase Supported Polymer Synthesis of Sequence-Defined, Multifunctional Poly(amidoamines) Hartmann, Laura; Krause, Eberhard; Antonietti, Markus Biomacromolecules, Vol. 7, Issue 4 https://doi.org/10.1021/bm050884k	journal	April 2006
Synthetic foldamers Guichard, Gilles; Huc, Ivan Chemical Communications, Vol. 47, Issue 21 https://doi.org/10.1039/c1cc11137j	journal	January 2011
Beyond de novo protein design — de novo design of non-natural folded oligomers Cheng, Richard P. Current Opinion in Structural Biology, Vol. 14, Issue 4 https://doi.org/10.1016/j.sbi.2004.07.001	journal	August 2004
Duplex Oligomers Defined via Covalent Casting of a One-Dimensional Hydrogen-Bonding Motif Archer, Eric A.; Krische, Michael J. Journal of the American Chemical Society, Vol. 124, Issue 18, p. 5074-5083 https://doi.org/10.1021/ja012696h	journal	May 2002
Reading Polymers: Sequencing of Natural and Synthetic Macromolecules Mutlu, Hatice; Lutz, Jean-François Angewandte Chemie International Edition, Vol. 53, Issue 48 https://doi.org/10.1002/anie.201406766	journal	October 2014
Development and testing of a general amber force field Wang, Junmei; Wolf, Romain M.; Caldwell, James W. Journal of Computational Chemistry, Vol. 25, Issue 9 https://doi.org/10.1002/jcc.20035	journal	January 2004
Synthesis, structural investigation and computational modelling of water-binding aquafoldamers Zhao, Huaiqing; Ong, Wei Qiang; Fang, Xiao Organic & Biomolecular Chemistry, Vol. 10, Issue 6, p. 1172-1180 https://doi.org/10.1039/C1OB06609A	journal	January 2012
Synthesis of Molecularly Encoded Oligomers Using a Chemoselective “AB + CD” Iterative Approach Trinh, Thanh Tam; Oswald, Laurence; Chan-Seng, Delphine Macromolecular Rapid Communications, Vol. 35, Issue 2 https://doi.org/10.1002/marc.201300774	journal	December 2013
ACPYPE - AnteChamber PYthon Parser interfacE Sousa da Silva, Alan W.; Vranken, Wim F. BMC Research Notes, Vol. 5, Issue 1 https://doi.org/10.1186/1756-0500-5-367	journal	January 2012
Convergent synthesis of digitally-encoded poly(alkoxyamine amide)s Roy, Raj Kumar; Laure, Chloé; Fischer-Krauser, Diane Chemical Communications, Vol. 51, Issue 86 https://doi.org/10.1039/C5CC06646H	journal	January 2015
Recent applications of 2,4,6-trichloro-1,3,5-triazine and its derivatives in organic synthesis Blotny, Grzegorz Tetrahedron, Vol. 62, Issue 41, p. 9507-9522 https://doi.org/10.1016/j.tet.2006.07.039	journal	October 2006
Triazinyl-Amino Acids, New Building Blocks for Pseudopeptides Zerkowski, Jonathan A.; Hensley, Laura M.; Abramowitz, David Synlett, Vol. 2002, Issue 4, p. 0557-0560 https://doi.org/10.1055/s-2002-22713	journal	January 2002
Multifunctionalized Sequence-Defined Oligomers from a Single Building Block Espeel, Pieter; Carrette, Lieselot L. G.; Bury, Katarzyna Angewandte Chemie International Edition, Vol. 52, Issue 50 https://doi.org/10.1002/anie.201307439	journal	October 2013
A General Approach to Sequence-Controlled Polymers Using Macrocyclic Ring Opening Metathesis Polymerization Gutekunst, Will R.; Hawker, Craig J. Journal of the American Chemical Society, Vol. 137, Issue 25 https://doi.org/10.1021/jacs.5b04940	journal	June 2015

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