Chemical functionalization of oligodeoxynucleotides with multiple boronic acids for the polyvalent binding of saccharides.
Published
Journal Article
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.
Full Text
Duke Authors
Cited Authors
- Hargrove, AE; Ellington, AD; Anslyn, EV; Sessler, JL
Published Date
- March 2011
Published In
Volume / Issue
- 22 / 3
Start / End Page
- 388 - 396
PubMed ID
- 21299200
Pubmed Central ID
- 21299200
Electronic International Standard Serial Number (EISSN)
- 1520-4812
International Standard Serial Number (ISSN)
- 1043-1802
Digital Object Identifier (DOI)
- 10.1021/bc100376x
Language
- eng