title: Synthesis of Small-Molecule/DNA Hybrids through On-Bead Amide-Coupling Approach.
abstract: Small molecule/DNA hybrids (SMDHs) have been considered as nanoscale building blocks for engineering 2D and 3D supramolecular DNA assembly. Herein, we report an efficient on-bead amide-coupling approach to prepare SMDHs with multiple oligodeoxynucleotide (ODN) strands. Our method is high yielding under mild and user-friendly conditions with various organic substrates and homo- or mixed-sequenced ODNs. Metal catalysts and moisture- and air-free conditions are not required. The products can be easily analyzed by LC-MS with accurate mass resolution. We also explored nanometer-sized shape-persistent macrocycles as novel multitopic organic linkers to prepare SMDHs. SMDHs bearing up to six ODNs were successfully prepared through the coupling of arylenethynylene macrocycles with ODNs, which were used to mediate the assembly of gold nanoparticles.
authors.affiliation: Department of Chemistry and Biochemistry and ‡Department of Chemical and Biological Engineering, University of Colorado at Boulder Boulder, Colorado 80309, United States.
authors.forename: Kenji D
authors.initials: KD
authors.lastname: Okochi
authors.affiliation: Department of Chemistry and Biochemistry and ‡Department of Chemical and Biological Engineering, University of Colorado at Boulder Boulder, Colorado 80309, United States.
authors.forename: Luca
authors.initials: L
authors.lastname: Monfregola
authors.affiliation: Department of Chemistry and Biochemistry and ‡Department of Chemical and Biological Engineering, University of Colorado at Boulder Boulder, Colorado 80309, United States.
authors.forename: Sarah Michelle
authors.initials: SM
authors.lastname: Dickerson
authors.affiliation: Department of Chemistry and Biochemistry and ‡Department of Chemical and Biological Engineering, University of Colorado at Boulder Boulder, Colorado 80309, United States.
authors.forename: Ryan
authors.initials: R
authors.lastname: McCaffrey
authors.affiliation: Department of Chemistry and Biochemistry and ‡Department of Chemical and Biological Engineering, University of Colorado at Boulder Boulder, Colorado 80309, United States.
authors.forename: Dylan W
authors.initials: DW
authors.lastname: Domaille
authors.affiliation: Department of Chemistry and Biochemistry and ‡Department of Chemical and Biological Engineering, University of Colorado at Boulder Boulder, Colorado 80309, United States.
authors.forename: Chao
authors.initials: C
authors.lastname: Yu
authors.affiliation: Department of Chemistry and Biochemistry and ‡Department of Chemical and Biological Engineering, University of Colorado at Boulder Boulder, Colorado 80309, United States.
authors.forename: Glenn R
authors.initials: GR
authors.lastname: Hafenstine
authors.affiliation: Department of Chemistry and Biochemistry and ‡Department of Chemical and Biological Engineering, University of Colorado at Boulder Boulder, Colorado 80309, United States.
authors.forename: Yinghua
authors.initials: Y
authors.lastname: Jin
authors.affiliation: Department of Chemistry and Biochemistry and ‡Department of Chemical and Biological Engineering, University of Colorado at Boulder Boulder, Colorado 80309, United States.
authors.forename: Jennifer N
authors.initials: JN
authors.lastname: Cha
authors.affiliation: Department of Chemistry and Biochemistry and ‡Department of Chemical and Biological Engineering, University of Colorado at Boulder Boulder, Colorado 80309, United States.
authors.forename: Robert D
authors.identifier: 0000-0003-3179-0239
authors.initials: RD
authors.lastname: Kuchta
authors.affiliation: Department of Chemistry and Biochemistry and ‡Department of Chemical and Biological Engineering, University of Colorado at Boulder Boulder, Colorado 80309, United States.
authors.forename: Marvin
authors.identifier: 0000-0002-4931-468X
authors.initials: M
authors.lastname: Caruthers
authors.affiliation: Department of Chemistry and Biochemistry and ‡Department of Chemical and Biological Engineering, University of Colorado at Boulder Boulder, Colorado 80309, United States.
authors.forename: Wei
authors.identifier: 0000-0002-5491-1155
authors.initials: W
authors.lastname: Zhang
mesh_terms: D000577:Amides / Q000737:chemistry*; D004247:DNA / Q000737:chemistry*; D015394:Molecular Structure; D009838:Oligodeoxyribonucleotides / Q000737:chemistry; D054852:Small Molecule Libraries / Q000737:chemistry*
chemical_list: D000577:Amides; D009838:Oligodeoxyribonucleotides; D054852:Small Molecule Libraries; D004247:DNA