DOE PAGES title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Sequence-directed dynamic covalent assembly of base-4-encoded oligomers

Abstract

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.

Authors:
ORCiD logo [1]; ORCiD logo [1]; ORCiD logo [2]
  1. Univ. of Michigan, Ann Arbor, MI (United States). Dept. of Chemical Engineering
  2. Univ. of Michigan, Ann Arbor, MI (United States). Dept. of Chemical Engineering; Monash Univ., Clayton, VIC (Australia). Dept. of Chemical Engineering. Dept. of Materials Science and Engineering
Publication Date:
Research Org.:
Univ. of Michigan, Ann Arbor, MI (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1802360
Alternate Identifier(s):
OSTI ID: 1636785
Grant/Contract Number:  
SC0012479
Resource Type:
Accepted Manuscript
Journal Name:
ChemComm
Additional Journal Information:
Journal Volume: 56; Journal Issue: 56; Journal ID: ISSN 1359-7345
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Leguizamon, S. C., Dunn, M. F., and Scott, T. F. Sequence-directed dynamic covalent assembly of base-4-encoded oligomers. United States: N. p., 2020. Web. doi:10.1039/d0cc01083a.
Leguizamon, S. C., Dunn, M. F., & Scott, T. F. Sequence-directed dynamic covalent assembly of base-4-encoded oligomers. United States. https://doi.org/10.1039/d0cc01083a
Leguizamon, S. C., Dunn, M. F., and Scott, T. F. Wed . "Sequence-directed dynamic covalent assembly of base-4-encoded oligomers". United States. https://doi.org/10.1039/d0cc01083a. https://www.osti.gov/servlets/purl/1802360.
@article{osti_1802360,
title = {Sequence-directed dynamic covalent assembly of base-4-encoded oligomers},
author = {Leguizamon, S. C. and Dunn, M. F. and Scott, T. F.},
abstractNote = {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.},
doi = {10.1039/d0cc01083a},
journal = {ChemComm},
number = 56,
volume = 56,
place = {United States},
year = {Wed Jun 24 00:00:00 EDT 2020},
month = {Wed Jun 24 00:00:00 EDT 2020}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record

Citation Metrics:
Cited by: 3 works
Citation information provided by
Web of Science

Save / Share:

Works referenced in this record:

Four Simultaneously Dynamic Covalent Reactions. Experimental Proof of Orthogonality
journal, August 2016

  • Seifert, Helen M.; Ramirez Trejo, Karina; Anslyn, Eric V.
  • Journal of the American Chemical Society, Vol. 138, Issue 34
  • DOI: 10.1021/jacs.6b04532

Yb(Otf) 3 ·H 2 O: A Novel Reagent for the Chemoselective Hydrolysis of Isopropylidene Acetals
journal, May 2001

  • Yadav, J. S.; Reddy, B. V. Subba; Reddy, K. Srinivasa
  • Chemistry Letters, Vol. 30, Issue 5
  • DOI: 10.1246/cl.2001.430

Rare-Earth Metal Triflates in Organic Synthesis
journal, June 2002

  • Kobayashi, Shū; Sugiura, Masaharu; Kitagawa, Hidetoshi
  • Chemical Reviews, Vol. 102, Issue 6
  • DOI: 10.1021/cr010289i

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

Molecular Structure of Nucleic Acids: A Structure for Deoxyribose Nucleic Acid
journal, April 1953

  • Watson, J. D.; Crick, F. H. C.
  • Nature, Vol. 171, Issue 4356
  • DOI: 10.1038/171737a0

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

In situ deprotection and dynamic covalent assembly using a dual role catalyst
journal, January 2017

  • Wei, T.; Furgal, J. C.; Scott, T. F.
  • Chemical Communications, Vol. 53, Issue 27
  • DOI: 10.1039/C7CC01028A

Molecular Stick-Slip Motion Revealed by Opening DNA with Piconewton Forces
journal, December 1997


Nucleic acid junctions and lattices
journal, November 1982


Complex shapes self-assembled from single-stranded DNA tiles
journal, May 2012


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

Orthogonal or simultaneous use of disulfide and hydrazone exchange in dynamic covalent chemistry in aqueous solution
journal, January 2008

  • Rodriguez-Docampo, Zaida; Otto, Sijbren
  • Chemical Communications, Issue 42
  • DOI: 10.1039/b808725c

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

Orthogonal breaking and forming of dynamic covalent imine and disulfide bonds in aqueous solution
journal, January 2015

  • Bracchi, Michael E.; Fulton, David A.
  • Chemical Communications, Vol. 51, Issue 55
  • DOI: 10.1039/C5CC02716K

An Iminoboronate Construction Set for Subcomponent Self-Assembly
journal, May 2008

  • Hutin, Marie; Bernardinelli, Gérald; Nitschke, Jonathan R.
  • Chemistry - A European Journal, Vol. 14, Issue 15
  • DOI: 10.1002/chem.200800074

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

Aqueous dynamic covalent assembly of molecular ladders and grids bearing boronate ester rungs
journal, January 2019

  • Dunn, Megan F.; Wei, Tao; Zuckermann, Ronald N.
  • Polymer Chemistry, Vol. 10, Issue 18
  • DOI: 10.1039/C8PY01705K

Sequence-selective dynamic covalent assembly of information-bearing oligomers
journal, February 2020


Folding DNA to create nanoscale shapes and patterns
journal, March 2006