Long, self-assembled molecular ladders by cooperative dynamic covalent reactions

Wei, Tao; Furgal, Joseph C.; Jung, Jae Hwan; Scott, Timothy F.

doi:10.1039/c6py01951j

Long, self-assembled molecular ladders by cooperative dynamic covalent reactions

Journal Article · Sun Jan 01 04:00:00 EST 2017 · Polymer Chemistry

DOI:https://doi.org/10.1039/c6py01951j· OSTI ID:1535153

Wei, Tao ^[1]; Furgal, Joseph C. ^[2]; Jung, Jae Hwan ^[3]; Scott, Timothy F. ^[4]

Department of Chemical Engineering; University of Michigan; Ann Arbor; USA; DOE/OSTI
Department of Chemical Engineering; University of Michigan; Ann Arbor; USA
Macromolecular Science and Engineering; University of Michigan; Ann Arbor; USA
Department of Chemical Engineering; University of Michigan; Ann Arbor; USA; Macromolecular Science and Engineering

The dynamic covalent self-assembly of peptoid-based oligomers bearingncomplementary functional groups yields molecular ladders withncovalent rungs.

Research Organization:: Univ. of Michigan, Ann Arbor, MI (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

DOE Contract Number:: SC0012479

OSTI ID:: 1535153

Journal Information:: Polymer Chemistry, Journal Name: Polymer Chemistry Journal Issue: 3 Vol. 8; ISSN PCOHC2; ISSN 1759-9954

Publisher:: Royal Society of Chemistry

Country of Publication:: United States

Language:: English

References (51)

Biomimetic Nanostructures: Creating a High-Affinity Zinc-Binding Site in a Folded Nonbiological Polymer Lee, Byoung-Chul; Chu, Tammy K.; Dill, Ken A. Journal of the American Chemical Society, Vol. 130, Issue 27 https://doi.org/10.1021/ja802125x	journal	July 2008
Recent advances in dynamic covalent chemistry Jin, Yinghua; Yu, Chao; Denman, Ryan J. Chemical Society Reviews, Vol. 42, Issue 16 https://doi.org/10.1039/c3cs60044k	journal	January 2013
Covalent ladder formation becomes kinetically trapped beyond four rungs Elliott, Erin L.; Hartley, C. Scott; Moore, Jeffrey S. Chemical Communications, Vol. 47, Issue 17 https://doi.org/10.1039/c1cc11242b	journal	January 2011
Dynamic combinatorial/covalent chemistry: a tool to read, generate and modulate the bioactivity of compounds and compound mixtures Herrmann, Andreas Chem. Soc. Rev., Vol. 43, Issue 6 https://doi.org/10.1039/C3CS60336A	journal	January 2014
HIV-1 TAR RNA Enhances the Interaction between Tat and Cyclin T1 Zhang, Jing; Tamilarasu, Natarajan; Hwang, Seongwoo Journal of Biological Chemistry, Vol. 275, Issue 44 https://doi.org/10.1074/jbc.M006804200	journal	August 2000
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
Design and synthesis of new fluorogenic HIV protease substrates based on resonance energy transfer Wang, Gary T.; Matayoshi, Edmund; Jan Huffaker, H. Tetrahedron Letters, Vol. 31, Issue 45, p. 6493-6496 https://doi.org/10.1016/S0040-4039(00)97099-0	journal	January 1990
Self-Assembly in Natural and Unnatural Systems Philp, Douglas; Stoddart, J. Fraser Angewandte Chemie International Edition in English, Vol. 35, Issue 11 https://doi.org/10.1002/anie.199611541	journal	June 1996
An autonomous molecular assembler for programmable chemical synthesis Meng, Wenjing; Muscat, Richard A.; McKee, Mireya L. Nature Chemistry, Vol. 8, Issue 6 https://doi.org/10.1038/nchem.2495	journal	April 2016
Incorporation of Unprotected Heterocyclic Side Chains into Peptoid Oligomers via Solid-Phase Submonomer Synthesis Burkoth, Timothy S.; Fafarman, Aaron T.; Charych, Deborah H. Journal of the American Chemical Society, Vol. 125, Issue 29 https://doi.org/10.1021/ja0352101	journal	July 2003
Supramolecular Chemistry: Concepts and Perspectives Lehn, Jean‐Marie https://doi.org/10.1002/3527607439	book	May 1995
Dynamic combinatorial libraries: new opportunities in systems chemistry Hunt, Rosemary A. R.; Otto, Sijbren Chem. Commun., Vol. 47, Issue 3 https://doi.org/10.1039/C0CC03759A	journal	January 2011
Folding DNA to create nanoscale shapes and patterns Rothemund, Paul W. K. Nature, Vol. 440, Issue 7082, p. 297-302 https://doi.org/10.1038/nature04586	journal	March 2006
Dynamic Covalent Assembly of Peptoid-Based Ladder Oligomers by Vernier Templating Wei, Tao; Jung, Jae Hwan; Scott, Timothy F. Journal of the American Chemical Society, Vol. 137, Issue 51 https://doi.org/10.1021/jacs.5b11251	journal	December 2015
Peptoid Oligomers with α-Chiral, Aromatic Side Chains: Sequence Requirements for the Formation of Stable Peptoid Helices Wu, Cindy W.; Sanborn, Tracy J.; Huang, Kai Journal of the American Chemical Society, Vol. 123, Issue 28 https://doi.org/10.1021/ja003154n	journal	July 2001
Dynamic DNA nanotechnology using strand-displacement reactions Zhang, David Yu; Seelig, Georg Nature Chemistry, Vol. 3, Issue 2 https://doi.org/10.1038/nchem.957	journal	January 2011
Structural dynamics of potassium-channel gating revealed by single-molecule FRET Wang, Shizhen; Vafabakhsh, Reza; Borschel, William F. Nature Structural & Molecular Biology, Vol. 23, Issue 1 https://doi.org/10.1038/nsmb.3138	journal	December 2015
Cooperative self-assembly: producing synthetic polymers with precise and concise primary structures Avestro, Alyssa-Jennifer; Belowich, Matthew E.; Stoddart, J. Fraser Chemical Society Reviews, Vol. 41, Issue 18 https://doi.org/10.1039/c2cs35167f	journal	January 2012
Folding a Nonbiological Polymer into a Compact Multihelical Structure Lee, Byoung-Chul; Zuckermann, Ronald N.; Dill, Ken A. Journal of the American Chemical Society, Vol. 127, Issue 31 https://doi.org/10.1021/ja0514904	journal	August 2005
Autonomous multistep organic synthesis in a single isothermal solution mediated by a DNA walker He, Yu; Liu, David R. Nature Nanotechnology, Vol. 5, Issue 11 https://doi.org/10.1038/nnano.2010.190	journal	October 2010
Complex shapes self-assembled from single-stranded DNA tiles Wei, Bryan; Dai, Mingjie; Yin, Peng Nature, Vol. 485, Issue 7400 https://doi.org/10.1038/nature11075	journal	May 2012
Molecular self-assembly and nanochemistry: a chemical strategy for the synthesis of nanostructures Whitesides, G.; Mathias, J.; Seto, C. Science, Vol. 254, Issue 5036 https://doi.org/10.1126/science.1962191	journal	November 1991
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
Control of Crystallization and Melting Behavior in Sequence Specific Polypeptoids Rosales, Adrianne M.; Murnen, Hannah K.; Zuckermann, Ronald N. Macromolecules, Vol. 43, Issue 13 https://doi.org/10.1021/ma1002563	journal	July 2010
Novel fluorogenic substrates for assaying retroviral proteases by resonance energy transfer Matayoshi, E.; Wang, G.; Krafft, G. Science, Vol. 247, Issue 4945 https://doi.org/10.1126/science.2106161	journal	February 1990
Accelerated Submonomer Solid-Phase Synthesis of Peptoids Incorporating Multiple Substituted N -Aryl Glycine Monomers Proulx, Caroline; Yoo, Stan; Connolly, Michael D. The Journal of Organic Chemistry, Vol. 80, Issue 21 https://doi.org/10.1021/acs.joc.5b01449	journal	August 2015
Self-assembly of a nanoscale DNA box with a controllable lid Andersen, Ebbe S.; Dong, Mingdong; Nielsen, Morten M. Nature, Vol. 459, Issue 7243 https://doi.org/10.1038/nature07971	journal	May 2009
Design, Synthesis, Assembly, and Engineering of Peptoid Nanosheets Robertson, Ellen J.; Battigelli, Alessia; Proulx, Caroline Accounts of Chemical Research, Vol. 49, Issue 3 https://doi.org/10.1021/acs.accounts.5b00439	journal	January 2016
Covalent Assembly of Molecular Ladders Hartley, C. Scott; Elliott, Erin L.; Moore, Jeffrey S. Journal of the American Chemical Society, Vol. 129, Issue 15 https://doi.org/10.1021/ja0690013	journal	April 2007
Incorporation of Chemoselective Functionalities into Peptoids via Solid-Phase Submonomer Synthesis Horn, Thomas; Lee, Byoung-Chul; Dill, Ken A. Bioconjugate Chemistry, Vol. 15, Issue 2 https://doi.org/10.1021/bc0341831	journal	March 2004
Three-Dimensional Structures Self-Assembled from DNA Bricks Ke, Y.; Ong, L. L.; Shih, W. M. Science, Vol. 338, Issue 6111 https://doi.org/10.1126/science.1227268	journal	November 2012
Supramolecular Chemistry Steed, Jonathan W.; Atwood, Jerry L. https://doi.org/10.1002/9780470740880	book	January 2009
The Chemistry of Imines. Layer, Robert W. Chemical Reviews, Vol. 63, Issue 5 https://doi.org/10.1021/cr60225a003	journal	October 1963
Amidines, isothioureas, and guanidines as nucleophilic catalysts Taylor, James E.; Bull, Steven D.; Williams, Jonathan M. J. Chemical Society Reviews, Vol. 41, Issue 6 https://doi.org/10.1039/c2cs15288f	journal	January 2012
Supramolecular systems chemistry Mattia, Elio; Otto, Sijbren Nature Nanotechnology, Vol. 10, Issue 2 https://doi.org/10.1038/nnano.2014.337	journal	February 2015
A Simple, Rapid and Sensitive FRET Assay for Botulinum Neurotoxin Serotype B Detection Guo, Jiubiao; Xu, Ci; Li, Xuechen PLoS ONE, Vol. 9, Issue 12 https://doi.org/10.1371/journal.pone.0114124	journal	December 2014
Control of DNA Strand Displacement Kinetics Using Toehold Exchange Zhang, David Yu; Winfree, Erik Journal of the American Chemical Society, Vol. 131, Issue 47 https://doi.org/10.1021/ja906987s	journal	December 2009
3DNA: a software package for the analysis, rebuilding and visualization of three-dimensional nucleic acid structures Lu, X. -J. Nucleic Acids Research, Vol. 31, Issue 17 https://doi.org/10.1093/nar/gkg680	journal	September 2003
Peptoids: a modular approach to drug discovery. Simon, R. J.; Kania, R. S.; Zuckermann, R. N. Proceedings of the National Academy of Sciences, Vol. 89, Issue 20 https://doi.org/10.1073/pnas.89.20.9367	journal	October 1992
Dynamic Covalent Chemistry Rowan, Stuart J.; Cantrill, Stuart J.; Cousins, Graham R. L. Angewandte Chemie International Edition, Vol. 41, Issue 6, p. 898-952 https://doi.org/10.1002/1521-3773(20020315)41:6<898::AID-ANIE898>3.0.CO;2-E	journal	March 2002
Perspectives in Chemistry-Steps towards Complex Matter Lehn, Jean-Marie Angewandte Chemie International Edition, Vol. 52, Issue 10 https://doi.org/10.1002/anie.201208397	journal	February 2013
Polyproline and the "spectroscopic ruler" revisited with single-molecule fluorescence Schuler, B.; Lipman, E. A.; Steinbach, P. J. Proceedings of the National Academy of Sciences, Vol. 102, Issue 8 https://doi.org/10.1073/pnas.0408164102	journal	February 2005
Dynamic Covalent Chemistry Approaches Toward Macrocycles, Molecular Cages, and Polymers Jin, Yinghua; Wang, Qi; Taynton, Philip Accounts of Chemical Research, Vol. 47, Issue 5 https://doi.org/10.1021/ar500037v	journal	April 2014
D _5h [PhSiO _1.5 ] ₁₀ synthesis via F ⁻ catalyzed rearrangement of [PhSiO _1.5 ] _n . An experimental/computational analysis of likely reaction pathways Furgal, Joseph C.; Goodson III, Theodore; Laine, Richard M. Dalton Transactions, Vol. 45, Issue 3 https://doi.org/10.1039/C5DT04182A	journal	January 2016
Determination of the persistence length of helical and non-helical polypeptoids in solution Rosales, Adrianne M.; Murnen, Hannah K.; Kline, Steven R. Soft Matter, Vol. 8, Issue 13 https://doi.org/10.1039/c2sm07092h	journal	January 2012
Sequence Programmable Peptoid Polymers for Diverse Materials Applications Knight, Abigail S.; Zhou, Effie Y.; Francis, Matthew B. Advanced Materials, Vol. 27, Issue 38 https://doi.org/10.1002/adma.201500275	journal	April 2015
Real time detection of DNA*RNA hybridization in living cells Sokol, D. L.; Zhang, X.; Lu, P. Proceedings of the National Academy of Sciences, Vol. 95, Issue 20 https://doi.org/10.1073/pnas.95.20.11538	journal	September 1998
Energy transfer: a spectroscopic ruler. Stryer, L.; Haugland, R. P. Proceedings of the National Academy of Sciences, Vol. 58, Issue 2 https://doi.org/10.1073/pnas.58.2.719	journal	August 1967
Peptoid origins Zuckermann, Ronald N. Biopolymers, Vol. 96, Issue 5 https://doi.org/10.1002/bip.21573	journal	December 2010
Peptoid nanosheets exhibit a new secondary-structure motif Mannige, Ranjan V.; Haxton, Thomas K.; Proulx, Caroline Nature, Vol. 526, Issue 7573 https://doi.org/10.1038/nature15363	journal	October 2015
Beyond molecules: Self-assembly of mesoscopic and macroscopic components Whitesides, G. M.; Boncheva, M. Proceedings of the National Academy of Sciences, Vol. 99, Issue 8, p. 4769-4774 https://doi.org/10.1073/pnas.082065899	journal	April 2002

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