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

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

Abstract

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.

Authors:

^[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

Publication Date:: 2019-05-08

Sponsoring Org.:: USDOE

OSTI Identifier:: 1505873

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

Resource Type:: Publisher's Accepted Manuscript

Journal Name:: Polymer Chemistry

Additional Journal Information:: Journal Name: Polymer Chemistry Journal Volume: 10 Journal Issue: 18; Journal ID: ISSN 1759-9954

Publisher:: Royal Society of Chemistry (RSC)

Country of Publication:: United Kingdom

Language:: English

Citation Formats


                    Dunn, Megan F., Wei, Tao, Zuckermann, Ronald N., and Scott, Timothy F.. Aqueous dynamic covalent assembly of molecular ladders and grids bearing boronate ester rungs.  United Kingdom: N. p., 2019. 
Web.  doi:10.1039/C8PY01705K.

Copy to clipboard


                    Dunn, Megan F., Wei, Tao, Zuckermann, Ronald N., & Scott, Timothy F.. Aqueous dynamic covalent assembly of molecular ladders and grids bearing boronate ester rungs.  United Kingdom.  https://doi.org/10.1039/C8PY01705K

Copy to clipboard


                    Dunn, Megan F., Wei, Tao, Zuckermann, Ronald N., and Scott, Timothy F.. Wed .  
"Aqueous dynamic covalent assembly of molecular ladders and grids bearing boronate ester rungs".  United Kingdom.  https://doi.org/10.1039/C8PY01705K.

Copy to clipboard


                    
@article{osti_1505873,

  title        = {Aqueous dynamic covalent assembly of molecular ladders and grids bearing boronate ester rungs},

  author       = {Dunn, Megan F. and Wei, Tao and Zuckermann, Ronald N. and Scott, Timothy F.},

  abstractNote = {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.},

  doi          = {10.1039/C8PY01705K},

  journal      = {Polymer Chemistry},

  number       = 18,

  volume       = 10,

  place        = {United Kingdom},

  year         = {2019},

  month        = {5}

}

Copy to clipboard

Journal Article:

Free Publicly Available Full Text

Accepted Manuscript (Publisher)

Publisher's Version of Record
https://doi.org/10.1039/C8PY01705K

Other availability

Search WorldCat to find libraries that may hold this journal

Citation Metrics:

Cited by: 11 works

Citation information provided by
Web of Science

Save / Share:

Export Metadata

Save to My Library

Works referenced in this record:

Elucidation of the Mechanism of the Reaction between Phenylboronic Acid and a Model Diol, Alizarin Red S
journal, January 2012

Tomsho, John W.; Benkovic, Stephen J.
The Journal of Organic Chemistry, Vol. 77, Issue 5
DOI: 10.1021/jo202250d

A Spectrophotometric Investigation of the Interaction of Iodine with Aromatic Hydrocarbons
journal, August 1949

Benesi, H. A.; Hildebrand, J. H.
Journal of the American Chemical Society, Vol. 71, Issue 8
DOI: 10.1021/ja01176a030

Stabilisation of self-assembled DNA crystals by triplex-directed photo-cross-linking
journal, January 2016

Abdallah, Hatem O.; Ohayon, Yoel P.; Chandrasekaran, Arun Richard
Chemical Communications, Vol. 52, Issue 51
DOI: 10.1039/C6CC03695C

Cyclization of peptoids by formation of boronate esters
journal, February 2012

Chirayil, Sara; Luebke, Kevin J.
Tetrahedron Letters, Vol. 53, Issue 7
DOI: 10.1016/j.tetlet.2011.12.002

Assembly of a Trifunctional Artificial Peptide Into an Anti-Parallel Duplex with Three Cu(II) Cross-links
journal, February 2011

Coppock, Matthew B.; Miller, James R.; Williams, Mary Elizabeth
Inorganic Chemistry, Vol. 50, Issue 3
DOI: 10.1021/ic101538v

Kinetically Trapped Tetrahedral Cages via Alkyne Metathesis
journal, February 2016

Lee, Semin; Yang, Anna; Moneypenny, Timothy P.
Journal of the American Chemical Society, Vol. 138, Issue 7
DOI: 10.1021/jacs.6b00468

Well-Defined, Reversible Boronate Crosslinked Nanocarriers for Targeted Drug Delivery in Response to Acidic pH Values and cis -Diols
journal, January 2012

Li, Yuanpei; Xiao, Wenwu; Xiao, Kai
Angewandte Chemie International Edition, Vol. 51, Issue 12
DOI: 10.1002/anie.201107144

Revisiting Boronate/Diol Complexation as a Double Stimulus-Responsive Bioconjugation
journal, April 2017

Gennari, Arianna; Gujral, Chirag; Hohn, Erwin
Bioconjugate Chemistry, Vol. 28, Issue 5
DOI: 10.1021/acs.bioconjchem.7b00080

A detailed examination of boronic acid–diol complexation
journal, June 2002

Springsteen, Greg; Wang, Binghe
Tetrahedron, Vol. 58, Issue 26, p. 5291-5300
DOI: 10.1016/S0040-4020(02)00489-1

Lipid Tubules: A Paradigm for Molecularly Engineered Structures
journal, December 1993

Schnur, J. M.
Science, Vol. 262, Issue 5140
DOI: 10.1126/science.262.5140.1669

Amplified Optical Nonlinearity in a Self-Assembled Double-Strand Conjugated Porphyrin Polymer Ladder
journal, August 2002

Screen, Thomas E. O.; Thorne, Jonathan R. G.; Denning, Robert G.
Journal of the American Chemical Society, Vol. 124, Issue 33
DOI: 10.1021/ja026205k

Fabrication of novel biomaterials through molecular self-assembly
journal, September 2003

Zhang, Shuguang
Nature Biotechnology, Vol. 21, Issue 10
DOI: 10.1038/nbt874

Multicomponent Assembly of Boronic Acid Based Macrocycles and Cages
journal, February 2008

Christinat, Nicolas; Scopelliti, Rosario; Severin, Kay
Angewandte Chemie International Edition, Vol. 47, Issue 10
DOI: 10.1002/anie.200705272

Boronic acid building blocks: tools for sensing and separation
journal, January 2011

Nishiyabu, Ryuhei; Kubo, Yuji; James, Tony D.
Chemical Communications, Vol. 47, Issue 4
DOI: 10.1039/c0cc02920c

Long, self-assembled molecular ladders by cooperative dynamic covalent reactions
journal, January 2017

Wei, Tao; Furgal, Joseph C.; Jung, Jae Hwan
Polymer Chemistry, Vol. 8, Issue 3
DOI: 10.1039/C6PY01951J

Universal Reaction Mechanism of Boronic Acids with Diols in Aqueous Solution: Kinetics and the Basic Concept of a Conditional Formation Constant
journal, August 2014

Furikado, Yuki; Nagahata, Tomomi; Okamoto, Takuya
Chemistry - A European Journal, Vol. 20, Issue 41
DOI: 10.1002/chem.201403719

Covalent Assembly of Molecular Ladders
journal, April 2007

Hartley, C. Scott; Elliott, Erin L.; Moore, Jeffrey S.
Journal of the American Chemical Society, Vol. 129, Issue 15
DOI: 10.1021/ja0690013

Dynamic covalent chemistry enables formation of antimicrobial peptide quaternary assemblies in a completely abiotic manner
journal, August 2017

Reuther, James F.; Dees, Justine L.; Kolesnichenko, Igor V.
Nature Chemistry, Vol. 10, Issue 1
DOI: 10.1038/nchem.2847

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

Zuckermann, Ronald N.; Kerr, Janice M.; Kent, Stephen B. H.
Journal of the American Chemical Society, Vol. 114, Issue 26
DOI: 10.1021/ja00052a076

Photo-Cross-Linking-Assisted Thermal Stability of DNA Origami Structures and Its Application for Higher-Temperature Self-Assembly
journal, September 2011

Rajendran, Arivazhagan; Endo, Masayuki; Katsuda, Yousuke
Journal of the American Chemical Society, Vol. 133, Issue 37
DOI: 10.1021/ja204546h

A Method for the Deprotection of Alkylpinacolyl Boronate Esters
journal, May 2011

Sun, Jing; Perfetti, Michael T.; Santos, Webster L.
The Journal of Organic Chemistry, Vol. 76, Issue 9
DOI: 10.1021/jo200250y

Mfold web server for nucleic acid folding and hybridization prediction
journal, July 2003

Zuker, M.
Nucleic Acids Research, Vol. 31, Issue 13
DOI: 10.1093/nar/gkg595

pH responsive self-healing hydrogels formed by boronate–catechol complexation
journal, January 2011

He, Lihong; Fullenkamp, Dominic E.; Rivera, José G.
Chemical Communications, Vol. 47, Issue 26
DOI: 10.1039/c1cc11928a

Conformations of peptoids in nanosheets result from the interplay of backbone energetics and intermolecular interactions
journal, May 2018

Edison, John R.; Spencer, Ryan K.; Butterfoss, Glenn L.
Proceedings of the National Academy of Sciences, Vol. 115, Issue 22
DOI: 10.1073/pnas.1800397115

Sequence-specific polypeptoids: A diverse family of heteropolymers with stable secondary structure
journal, April 1998

Kirshenbaum, K.; Barron, A. E.; Goldsmith, R. A.
Proceedings of the National Academy of Sciences, Vol. 95, Issue 8
DOI: 10.1073/pnas.95.8.4303

Indicator–displacement assays
journal, December 2006

Nguyen, Binh T.; Anslyn, Eric V.
Coordination Chemistry Reviews, Vol. 250, Issue 23-24
DOI: 10.1016/j.ccr.2006.04.009

Porous, Crystalline, Covalent Organic Frameworks
journal, November 2005

Côté, Adrien P.; Benin, Annabelle I.; Ockwig, Nathan W.
Science, Vol. 310, Issue 5751, p. 1166-1170
DOI: 10.1126/science.1120411

The oxidation of catechol and homocatechol by tyrosinase in the presence of amino-acids
journal, January 1949

Jackson, H.; Kendal, L. P.
Biochemical Journal, Vol. 44, Issue 4
DOI: 10.1042/bj0440477

Multicomponent Assembly of Boron-Based Dendritic Nanostructures
journal, March 2007

Christinat, Nicolas; Scopelliti, Rosario; Severin, Kay
The Journal of Organic Chemistry, Vol. 72, Issue 6
DOI: 10.1021/jo062607p

Degradation Pathways of a Peptide Boronic Acid Derivative, 2‐Pyz‐(CO)‐Phe‐Leu‐B(OH)2
journal, June 2000

Wu, Sara; Waugh, Wanda; Stella, Valentino J.
Journal of Pharmaceutical Sciences, Vol. 89, Issue 6
DOI: 10.1002/(SICI)1520-6017(200006)89:6<758::AID-JPS7>3.0.CO;2-L

Cooperative Self-Assembly of Double-Strand Conjugated Porphyrin Ladders
journal, December 1999

Taylor, Peter N.; Anderson, Harry L.
Journal of the American Chemical Society, Vol. 121, Issue 49
DOI: 10.1021/ja992821d

Alizarin Red S. as a general optical reporter for studying the binding of boronic acids with carbohydrates
journal, January 2001

Springsteen, Greg; Wang, Binghe
Chemical Communications, Issue 17
DOI: 10.1039/b104895n

Protein folding in the cell
journal, January 1992

Gething, Mary-Jane; Sambrook, Joseph
Nature, Vol. 355, Issue 6355
DOI: 10.1038/355033a0

Covalent ladder formation becomes kinetically trapped beyond four rungs
journal, January 2011

Elliott, Erin L.; Hartley, C. Scott; Moore, Jeffrey S.
Chemical Communications, Vol. 47, Issue 17
DOI: 10.1039/c1cc11242b

Dynamic Covalent Assembly of Peptoid-Based Ladder Oligomers by Vernier Templating
journal, December 2015

Wei, Tao; Jung, Jae Hwan; Scott, Timothy F.
Journal of the American Chemical Society, Vol. 137, Issue 51
DOI: 10.1021/jacs.5b11251

Dynamic Covalent Chemistry
journal, March 2002

Rowan, Stuart J.; Cantrill, Stuart J.; Cousins, Graham R. L.
Angewandte Chemie International Edition, Vol. 41, Issue 6, p. 898-952
DOI: 10.1002/1521-3773(20020315)41:6<898::AID-ANIE898>3.0.CO;2-E

Boronic acid-based chemical sensors for saccharides
journal, November 2017

Zhang, Xiao-tai; Liu, Guang-jian; Ning, Zhang-wei
Carbohydrate Research, Vol. 452
DOI: 10.1016/j.carres.2017.10.010

The relationship among pKa, pH, and binding constants in the interactions between boronic acids and diols—it is not as simple as it appears
journal, November 2004

Yan, Jun; Springsteen, Greg; Deeter, Susan
Tetrahedron, Vol. 60, Issue 49
DOI: 10.1016/j.tet.2004.08.051

Multivalency and Cooperativity in Supramolecular Chemistry
journal, September 2005

Badjić, Jovica D.; Nelson, Alshakim; Cantrill, Stuart J.
Accounts of Chemical Research, Vol. 38, Issue 9
DOI: 10.1021/ar040223k

Two-Dimensional Metallo-supramolecular Polymerization: Toward Size-Controlled Multi-strand Polymers
journal, November 2012

Adisoejoso, Jinne; Li, Yang; Liu, Jun
Journal of the American Chemical Society, Vol. 134, Issue 45
DOI: 10.1021/ja308480x

Construction of Covalent Organic Nanotubes by Light-Induced Cross-Linking of Diacetylene-Based Helical Polymers
journal, August 2016

Maeda, Kaho; Hong, Liu; Nishihara, Taishi
Journal of the American Chemical Society, Vol. 138, Issue 34
DOI: 10.1021/jacs.6b05582

Similar Records in DOE PAGES and OSTI.GOV collections:

Sequence-selective dynamic covalent assembly of information-bearing oligomers

Journal Article Leguizamon, Samuel C. ; Scott, Timothy F. - Nature Communications

Relatively robust dynamic covalent interactions have been employed extensively to mediate molecular self-assembly reactions; however, these assembly processes often do not converge to a thermodynamic equilibrium, instead yielding mixtures of kinetically-trapped species. Here, we report a dynamic covalent self-assembly process that mitigates kinetic trapping such that multiple unique oligomers bearing covalently coreactive pendant groups are able to undergo simultaneous, sequence-selective hybridization with their complementary strands to afford biomimetic, in-registry molecular ladders with covalent rungs. Analogous to the thermal cycling commonly employed for nucleic acid melting and annealing, this is achieved by raising and lowering the concentration of a multi-role reagentmore »« less
Cited by 20
https://doi.org/10.1038/s41467-020-14607-3

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

Journal Article Leguizamon, Samuel C. ; Alqubati, Abdulla F. ; Scott, Timothy F. - Polymer Chemistry

Dynamic covalent self-assembly processes often exhibit poor capacities for error-correction owing to the relatively low connectivity rearrangement rates of dynamic covalent interactions and the common use of reaction conditions where the equilibrium state remains fixed. Here, we report a dynamic covalent self-assembly technique employing temperature, a conventional, externally-applied stimulus, to mediate the hybridization of peptoid oligomers bearing maleimide- and furan-based pendant groups to afford molecular ladders incorporating Diels–Alder adduct-based rungs. By raising or lowing the reaction temperature, this system enables the equilibrium state to be readily varied without altering reagent concentrations. Both triethylamine and the Lewis acidic scandium triflate weremore »« less
https://doi.org/10.1039/d0py01296c

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

Journal Article Wei, Tao ; Furgal, Joseph C. ; Jung, Jae Hwan ; ... - Polymer Chemistry

The dynamic covalent self-assembly of peptoid-based oligomers bearingncomplementary functional groups yields molecular ladders withncovalent rungs.
https://doi.org/10.1039/c6py01951j
Sequence-directed dynamic covalent assembly of base-4-encoded oligomers

Journal Article Leguizamon, S. C. ; Dunn, M. F. ; Scott, T. F. - ChemComm

As an information-bearing biomacromolecule, DNA is encoded in base-4, where each residue site can be occupied by any one of four nucleobases. Mimicking the information dense, sequence-selective hybridization of DNA, we demonstrate two orthogonal dynamic covalent interactions to effect the selective assembly of molecular ladders and grids from base-4-encoded oligo(peptoid)s.
Cited by 3
https://doi.org/10.1039/d0cc01083a

Full Text Available
IPA-CuCl₃: a S=1/2 Ladder with Ferromagnetic Rungs

Conference Masuda, Takatsugu ; Zheludev, Andrey I ; Manaka, H. ; ...

The spin gap material IPA-CuCl{sub 3} has been extensively studied as a ferromagnetic-antiferromagnetic bond-alternating S = 1/2 chain. This description of the system was derived from structural considerations and bulk measurements. New inelastic neutron scattering experiments reveal a totally different picture: IPA-CuCl{sub 3} consists of weakly coupled spin ladders with antiferromagnetic legs and ferromagnetic rungs. The ladders run perpendicular to the originally supposed bond-alternating chain direction. The ferromagnetic rungs make this system equivalent to a Haldane S = 1 antiferromagnet. With a gap energy of 1.17(1) meV, a zone-boundary energy of 4.1(1) meV, and almost no magnetic anisotropy, IPA-CuCl{sub 3}more »« less

Similar Records

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

Abstract

Citation Formats

Elucidation of the Mechanism of the Reaction between Phenylboronic Acid and a Model Diol, Alizarin Red S journal, January 2012

A Spectrophotometric Investigation of the Interaction of Iodine with Aromatic Hydrocarbons journal, August 1949

Stabilisation of self-assembled DNA crystals by triplex-directed photo-cross-linking journal, January 2016

Cyclization of peptoids by formation of boronate esters journal, February 2012

Assembly of a Trifunctional Artificial Peptide Into an Anti-Parallel Duplex with Three Cu(II) Cross-links journal, February 2011

Kinetically Trapped Tetrahedral Cages via Alkyne Metathesis journal, February 2016

Well-Defined, Reversible Boronate Crosslinked Nanocarriers for Targeted Drug Delivery in Response to Acidic pH Values and cis -Diols journal, January 2012

Revisiting Boronate/Diol Complexation as a Double Stimulus-Responsive Bioconjugation journal, April 2017

A detailed examination of boronic acid–diol complexation journal, June 2002

Lipid Tubules: A Paradigm for Molecularly Engineered Structures journal, December 1993

Amplified Optical Nonlinearity in a Self-Assembled Double-Strand Conjugated Porphyrin Polymer Ladder journal, August 2002

Fabrication of novel biomaterials through molecular self-assembly journal, September 2003

Multicomponent Assembly of Boronic Acid Based Macrocycles and Cages journal, February 2008

Boronic acid building blocks: tools for sensing and separation journal, January 2011

Long, self-assembled molecular ladders by cooperative dynamic covalent reactions journal, January 2017

Universal Reaction Mechanism of Boronic Acids with Diols in Aqueous Solution: Kinetics and the Basic Concept of a Conditional Formation Constant journal, August 2014

Covalent Assembly of Molecular Ladders journal, April 2007

Dynamic covalent chemistry enables formation of antimicrobial peptide quaternary assemblies in a completely abiotic manner journal, August 2017

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

Photo-Cross-Linking-Assisted Thermal Stability of DNA Origami Structures and Its Application for Higher-Temperature Self-Assembly journal, September 2011

A Method for the Deprotection of Alkylpinacolyl Boronate Esters journal, May 2011

Mfold web server for nucleic acid folding and hybridization prediction journal, July 2003

pH responsive self-healing hydrogels formed by boronate–catechol complexation journal, January 2011

Conformations of peptoids in nanosheets result from the interplay of backbone energetics and intermolecular interactions journal, May 2018

Sequence-specific polypeptoids: A diverse family of heteropolymers with stable secondary structure journal, April 1998

Indicator–displacement assays journal, December 2006

Porous, Crystalline, Covalent Organic Frameworks journal, November 2005

The oxidation of catechol and homocatechol by tyrosinase in the presence of amino-acids journal, January 1949

Multicomponent Assembly of Boron-Based Dendritic Nanostructures journal, March 2007

Degradation Pathways of a Peptide Boronic Acid Derivative, 2‐Pyz‐(CO)‐Phe‐Leu‐B(OH)2 journal, June 2000

Cooperative Self-Assembly of Double-Strand Conjugated Porphyrin Ladders journal, December 1999

Alizarin Red S. as a general optical reporter for studying the binding of boronic acids with carbohydrates journal, January 2001

Protein folding in the cell journal, January 1992

Covalent ladder formation becomes kinetically trapped beyond four rungs journal, January 2011

Dynamic Covalent Assembly of Peptoid-Based Ladder Oligomers by Vernier Templating journal, December 2015

Dynamic Covalent Chemistry journal, March 2002

Boronic acid-based chemical sensors for saccharides journal, November 2017

The relationship among pKa, pH, and binding constants in the interactions between boronic acids and diols—it is not as simple as it appears journal, November 2004

Multivalency and Cooperativity in Supramolecular Chemistry journal, September 2005

Two-Dimensional Metallo-supramolecular Polymerization: Toward Size-Controlled Multi-strand Polymers journal, November 2012

Construction of Covalent Organic Nanotubes by Light-Induced Cross-Linking of Diacetylene-Based Helical Polymers journal, August 2016

Elucidation of the Mechanism of the Reaction between Phenylboronic Acid and a Model Diol, Alizarin Red S
journal, January 2012

A Spectrophotometric Investigation of the Interaction of Iodine with Aromatic Hydrocarbons
journal, August 1949

Stabilisation of self-assembled DNA crystals by triplex-directed photo-cross-linking
journal, January 2016

Cyclization of peptoids by formation of boronate esters
journal, February 2012

Assembly of a Trifunctional Artificial Peptide Into an Anti-Parallel Duplex with Three Cu(II) Cross-links
journal, February 2011

Kinetically Trapped Tetrahedral Cages via Alkyne Metathesis
journal, February 2016

Well-Defined, Reversible Boronate Crosslinked Nanocarriers for Targeted Drug Delivery in Response to Acidic pH Values and cis -Diols
journal, January 2012

Revisiting Boronate/Diol Complexation as a Double Stimulus-Responsive Bioconjugation
journal, April 2017

A detailed examination of boronic acid–diol complexation
journal, June 2002

Lipid Tubules: A Paradigm for Molecularly Engineered Structures
journal, December 1993

Amplified Optical Nonlinearity in a Self-Assembled Double-Strand Conjugated Porphyrin Polymer Ladder
journal, August 2002

Fabrication of novel biomaterials through molecular self-assembly
journal, September 2003

Multicomponent Assembly of Boronic Acid Based Macrocycles and Cages
journal, February 2008

Boronic acid building blocks: tools for sensing and separation
journal, January 2011

Long, self-assembled molecular ladders by cooperative dynamic covalent reactions
journal, January 2017

Universal Reaction Mechanism of Boronic Acids with Diols in Aqueous Solution: Kinetics and the Basic Concept of a Conditional Formation Constant
journal, August 2014

Covalent Assembly of Molecular Ladders
journal, April 2007

Dynamic covalent chemistry enables formation of antimicrobial peptide quaternary assemblies in a completely abiotic manner
journal, August 2017

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

Photo-Cross-Linking-Assisted Thermal Stability of DNA Origami Structures and Its Application for Higher-Temperature Self-Assembly
journal, September 2011

A Method for the Deprotection of Alkylpinacolyl Boronate Esters
journal, May 2011

Mfold web server for nucleic acid folding and hybridization prediction
journal, July 2003

pH responsive self-healing hydrogels formed by boronate–catechol complexation
journal, January 2011

Conformations of peptoids in nanosheets result from the interplay of backbone energetics and intermolecular interactions
journal, May 2018

Sequence-specific polypeptoids: A diverse family of heteropolymers with stable secondary structure
journal, April 1998

Indicator–displacement assays
journal, December 2006

Porous, Crystalline, Covalent Organic Frameworks
journal, November 2005

The oxidation of catechol and homocatechol by tyrosinase in the presence of amino-acids
journal, January 1949

Multicomponent Assembly of Boron-Based Dendritic Nanostructures
journal, March 2007

Degradation Pathways of a Peptide Boronic Acid Derivative, 2‐Pyz‐(CO)‐Phe‐Leu‐B(OH)2
journal, June 2000

Cooperative Self-Assembly of Double-Strand Conjugated Porphyrin Ladders
journal, December 1999

Alizarin Red S. as a general optical reporter for studying the binding of boronic acids with carbohydrates
journal, January 2001

Protein folding in the cell
journal, January 1992

Covalent ladder formation becomes kinetically trapped beyond four rungs
journal, January 2011

Dynamic Covalent Assembly of Peptoid-Based Ladder Oligomers by Vernier Templating
journal, December 2015

Dynamic Covalent Chemistry
journal, March 2002

Boronic acid-based chemical sensors for saccharides
journal, November 2017

The relationship among pKa, pH, and binding constants in the interactions between boronic acids and diols—it is not as simple as it appears
journal, November 2004

Multivalency and Cooperativity in Supramolecular Chemistry
journal, September 2005

Two-Dimensional Metallo-supramolecular Polymerization: Toward Size-Controlled Multi-strand Polymers
journal, November 2012

Construction of Covalent Organic Nanotubes by Light-Induced Cross-Linking of Diacetylene-Based Helical Polymers
journal, August 2016