title: Chemical functionalization of oligodeoxynucleotides with multiple boronic acids for the polyvalent binding of saccharides.
abstract: A novel saccharide host containing four boronic acid recognition units on a single DNA duplex terminus was constructed. This construct allowed boronic acid sugar recognition in the context of double-stranded DNA to be established while highlighting the benefits of multivalency. Following the solid-phase synthesis of a bis-boronic acid tag, two end-functionalized oligonucleotides with complementary sequences were functionalized through amide ligation. By annealing the boronic acid-DNA conjugates, a tetra-boronic acid DNA duplex was assembled. The saccharide binding ability of this tetra-boronic acid host was revealed through cellulose paper chromatography in the absence and presence of various saccharides. While no appreciable saccharide binding was seen in the case of a bis-boronic DNA conjugate, the increased migration of the tetra-boronic acid host relative to the control sequences in the presence of selected monosaccharides underscored the importance of multivalent effects. We thus identified a requirement for multiple recognition sites in these conjugate systems and expect the results to facilitate future efforts toward applying synthetic recognition systems to the realm of macromolecules.
authors.affiliation: Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, Texas 78712-0165, USA.
authors.forename: Amanda E
authors.initials: AE
authors.lastname: Hargrove
authors.forename: Andrew D
authors.initials: AD
authors.lastname: Ellington
authors.forename: Eric V
authors.initials: EV
authors.lastname: Anslyn
authors.forename: Jonathan L
authors.initials: JL
authors.lastname: Sessler
mesh_terms: D001483:Base Sequence; D001897:Boronic Acids / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D002854:Chromatography, Paper; D004247:DNA / Q000737:chemistry / Q000235:genetics; D009838:Oligodeoxyribonucleotides / Q000737:chemistry* / Q000235:genetics
chemical_list: D001897:Boronic Acids; D002241:Carbohydrates; D009838:Oligodeoxyribonucleotides; D004247:DNA