Aqueous dynamic covalent assembly of molecular ladders and grids bearing boronate ester rungs

Dunn, Megan F.; Wei, Tao; Zuckermann, Ronald N.; Scott, Timothy F.

doi:10.1039/C8PY01705K

Aqueous dynamic covalent assembly of molecular ladders and grids bearing boronate ester rungs

Journal Article · Wed May 08 00:00:00 EDT 2019 · Polymer Chemistry

DOI:https://doi.org/10.1039/C8PY01705K· OSTI ID:1505873

^[1]; ^[1]; ^[2]; ^[3]

Department of Chemical Engineering, University of Michigan, Ann Arbor, USA
Molecular Foundry, Lawrence Berkeley National Laboratory, Berkeley, USA
Department of Chemical Engineering, University of Michigan, Ann Arbor, USA, Macromolecular Science and Engineering

Mimicking the self-assembly of nucleic acid sequences into double-stranded molecular ladders that incorporate hydrogen bond-based rungs, dynamic covalent interactions enable the fabrication of molecular ladder and grid structures with covalent bond-based rungs.

View Accepted Manuscript (Publisher)

Sponsoring Organization:: USDOE

Grant/Contract Number:: AC02-05CH11231; SC0012479

OSTI ID:: 1505873

Journal Information:: Polymer Chemistry, Journal Name: Polymer Chemistry Journal Issue: 18 Vol. 10; ISSN PCOHC2; ISSN 1759-9954

Publisher:: Royal Society of Chemistry (RSC)Copyright Statement

Country of Publication:: United Kingdom

Language:: English

References (41)

Degradation Pathways of a Peptide Boronic Acid Derivative, 2‐Pyz‐(CO)‐Phe‐Leu‐B(OH)2 Wu, Sara; Waugh, Wanda; Stella, Valentino J. Journal of Pharmaceutical Sciences, Vol. 89, Issue 6 https://doi.org/10.1002/(SICI)1520-6017(200006)89:6<758::AID-JPS7>3.0.CO;2-L	journal	June 2000
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
Multicomponent Assembly of Boronic Acid Based Macrocycles and Cages Christinat, Nicolas; Scopelliti, Rosario; Severin, Kay Angewandte Chemie International Edition, Vol. 47, Issue 10 https://doi.org/10.1002/anie.200705272	journal	February 2008
Well-Defined, Reversible Boronate Crosslinked Nanocarriers for Targeted Drug Delivery in Response to Acidic pH Values and cis -Diols Li, Yuanpei; Xiao, Wenwu; Xiao, Kai Angewandte Chemie International Edition, Vol. 51, Issue 12 https://doi.org/10.1002/anie.201107144	journal	January 2012
Universal Reaction Mechanism of Boronic Acids with Diols in Aqueous Solution: Kinetics and the Basic Concept of a Conditional Formation Constant Furikado, Yuki; Nagahata, Tomomi; Okamoto, Takuya Chemistry - A European Journal, Vol. 20, Issue 41 https://doi.org/10.1002/chem.201403719	journal	August 2014
A detailed examination of boronic acid–diol complexation Springsteen, Greg; Wang, Binghe Tetrahedron, Vol. 58, Issue 26, p. 5291-5300 https://doi.org/10.1016/S0040-4020(02)00489-1	journal	June 2002
Boronic acid-based chemical sensors for saccharides Zhang, Xiao-tai; Liu, Guang-jian; Ning, Zhang-wei Carbohydrate Research, Vol. 452 https://doi.org/10.1016/j.carres.2017.10.010	journal	November 2017
Indicator–displacement assays Nguyen, Binh T.; Anslyn, Eric V. Coordination Chemistry Reviews, Vol. 250, Issue 23-24 https://doi.org/10.1016/j.ccr.2006.04.009	journal	December 2006
The relationship among pKa, pH, and binding constants in the interactions between boronic acids and diols—it is not as simple as it appears Yan, Jun; Springsteen, Greg; Deeter, Susan Tetrahedron, Vol. 60, Issue 49 https://doi.org/10.1016/j.tet.2004.08.051	journal	November 2004
Cyclization of peptoids by formation of boronate esters Chirayil, Sara; Luebke, Kevin J. Tetrahedron Letters, Vol. 53, Issue 7 https://doi.org/10.1016/j.tetlet.2011.12.002	journal	February 2012
Revisiting Boronate/Diol Complexation as a Double Stimulus-Responsive Bioconjugation Gennari, Arianna; Gujral, Chirag; Hohn, Erwin Bioconjugate Chemistry, Vol. 28, Issue 5 https://doi.org/10.1021/acs.bioconjchem.7b00080	journal	April 2017
Multivalency and Cooperativity in Supramolecular Chemistry Badjić, Jovica D.; Nelson, Alshakim; Cantrill, Stuart J. Accounts of Chemical Research, Vol. 38, Issue 9 https://doi.org/10.1021/ar040223k	journal	September 2005
Assembly of a Trifunctional Artificial Peptide Into an Anti-Parallel Duplex with Three Cu(II) Cross-links Coppock, Matthew B.; Miller, James R.; Williams, Mary Elizabeth Inorganic Chemistry, Vol. 50, Issue 3 https://doi.org/10.1021/ic101538v	journal	February 2011
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
A Spectrophotometric Investigation of the Interaction of Iodine with Aromatic Hydrocarbons Benesi, H. A.; Hildebrand, J. H. Journal of the American Chemical Society, Vol. 71, Issue 8 https://doi.org/10.1021/ja01176a030	journal	August 1949
Amplified Optical Nonlinearity in a Self-Assembled Double-Strand Conjugated Porphyrin Polymer Ladder Screen, Thomas E. O.; Thorne, Jonathan R. G.; Denning, Robert G. Journal of the American Chemical Society, Vol. 124, Issue 33 https://doi.org/10.1021/ja026205k	journal	August 2002
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
Photo-Cross-Linking-Assisted Thermal Stability of DNA Origami Structures and Its Application for Higher-Temperature Self-Assembly Rajendran, Arivazhagan; Endo, Masayuki; Katsuda, Yousuke Journal of the American Chemical Society, Vol. 133, Issue 37 https://doi.org/10.1021/ja204546h	journal	September 2011
Two-Dimensional Metallo-supramolecular Polymerization: Toward Size-Controlled Multi-strand Polymers Adisoejoso, Jinne; Li, Yang; Liu, Jun Journal of the American Chemical Society, Vol. 134, Issue 45 https://doi.org/10.1021/ja308480x	journal	November 2012
Cooperative Self-Assembly of Double-Strand Conjugated Porphyrin Ladders Taylor, Peter N.; Anderson, Harry L. Journal of the American Chemical Society, Vol. 121, Issue 49 https://doi.org/10.1021/ja992821d	journal	December 1999
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
Kinetically Trapped Tetrahedral Cages via Alkyne Metathesis Lee, Semin; Yang, Anna; Moneypenny, Timothy P. Journal of the American Chemical Society, Vol. 138, Issue 7 https://doi.org/10.1021/jacs.6b00468	journal	February 2016
Construction of Covalent Organic Nanotubes by Light-Induced Cross-Linking of Diacetylene-Based Helical Polymers Maeda, Kaho; Hong, Liu; Nishihara, Taishi Journal of the American Chemical Society, Vol. 138, Issue 34 https://doi.org/10.1021/jacs.6b05582	journal	August 2016
Multicomponent Assembly of Boron-Based Dendritic Nanostructures Christinat, Nicolas; Scopelliti, Rosario; Severin, Kay The Journal of Organic Chemistry, Vol. 72, Issue 6 https://doi.org/10.1021/jo062607p	journal	March 2007
A Method for the Deprotection of Alkylpinacolyl Boronate Esters Sun, Jing; Perfetti, Michael T.; Santos, Webster L. The Journal of Organic Chemistry, Vol. 76, Issue 9 https://doi.org/10.1021/jo200250y	journal	May 2011
Elucidation of the Mechanism of the Reaction between Phenylboronic Acid and a Model Diol, Alizarin Red S Tomsho, John W.; Benkovic, Stephen J. The Journal of Organic Chemistry, Vol. 77, Issue 5 https://doi.org/10.1021/jo202250d	journal	January 2012
Protein folding in the cell Gething, Mary-Jane; Sambrook, Joseph Nature, Vol. 355, Issue 6355 https://doi.org/10.1038/355033a0	journal	January 1992
Fabrication of novel biomaterials through molecular self-assembly Zhang, Shuguang Nature Biotechnology, Vol. 21, Issue 10 https://doi.org/10.1038/nbt874	journal	September 2003
Dynamic covalent chemistry enables formation of antimicrobial peptide quaternary assemblies in a completely abiotic manner Reuther, James F.; Dees, Justine L.; Kolesnichenko, Igor V. Nature Chemistry, Vol. 10, Issue 1 https://doi.org/10.1038/nchem.2847	journal	August 2017
Stabilisation of self-assembled DNA crystals by triplex-directed photo-cross-linking Abdallah, Hatem O.; Ohayon, Yoel P.; Chandrasekaran, Arun Richard Chemical Communications, Vol. 52, Issue 51 https://doi.org/10.1039/C6CC03695C	journal	January 2016
Long, self-assembled molecular ladders by cooperative dynamic covalent reactions Wei, Tao; Furgal, Joseph C.; Jung, Jae Hwan Polymer Chemistry, Vol. 8, Issue 3 https://doi.org/10.1039/C6PY01951J	journal	January 2017
Alizarin Red S. as a general optical reporter for studying the binding of boronic acids with carbohydrates Springsteen, Greg; Wang, Binghe Chemical Communications, Issue 17 https://doi.org/10.1039/b104895n	journal	January 2001
Boronic acid building blocks: tools for sensing and separation Nishiyabu, Ryuhei; Kubo, Yuji; James, Tony D. Chemical Communications, Vol. 47, Issue 4 https://doi.org/10.1039/c0cc02920c	journal	January 2011
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
pH responsive self-healing hydrogels formed by boronate–catechol complexation He, Lihong; Fullenkamp, Dominic E.; Rivera, José G. Chemical Communications, Vol. 47, Issue 26 https://doi.org/10.1039/c1cc11928a	journal	January 2011
The oxidation of catechol and homocatechol by tyrosinase in the presence of amino-acids Jackson, H.; Kendal, L. P. Biochemical Journal, Vol. 44, Issue 4 https://doi.org/10.1042/bj0440477	journal	January 1949
Conformations of peptoids in nanosheets result from the interplay of backbone energetics and intermolecular interactions Edison, John R.; Spencer, Ryan K.; Butterfoss, Glenn L. Proceedings of the National Academy of Sciences, Vol. 115, Issue 22 https://doi.org/10.1073/pnas.1800397115	journal	May 2018
Sequence-specific polypeptoids: A diverse family of heteropolymers with stable secondary structure Kirshenbaum, K.; Barron, A. E.; Goldsmith, R. A. Proceedings of the National Academy of Sciences, Vol. 95, Issue 8 https://doi.org/10.1073/pnas.95.8.4303	journal	April 1998
Mfold web server for nucleic acid folding and hybridization prediction Zuker, M. Nucleic Acids Research, Vol. 31, Issue 13 https://doi.org/10.1093/nar/gkg595	journal	July 2003
Porous, Crystalline, Covalent Organic Frameworks Côté, Adrien P.; Benin, Annabelle I.; Ockwig, Nathan W. Science, Vol. 310, Issue 5751, p. 1166-1170 https://doi.org/10.1126/science.1120411	journal	November 2005
Lipid Tubules: A Paradigm for Molecularly Engineered Structures Schnur, J. M. Science, Vol. 262, Issue 5140 https://doi.org/10.1126/science.262.5140.1669	journal	December 1993

Similar Records

Sequence-selective dynamic covalent assembly of information-bearing oligomers

Journal Article · Thu Feb 06 19:00:00 EST 2020 · Nature Communications · OSTI ID:1624249

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

Journal Article · Sat Dec 31 23:00:00 EST 2016 · Polymer Chemistry · OSTI ID:1535153

Temperature-mediated molecular ladder self-assembly employing Diels–Alder cycloaddition

Journal Article · Tue Nov 17 19:00:00 EST 2020 · Polymer Chemistry · OSTI ID:1851647

Aqueous dynamic covalent assembly of molecular ladders and grids bearing boronate ester rungs

Citation Formats

References (41)

Similar Records

Related Subjects