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Updated: Mar 8, 2026

Nucleoside Triphosphates - From Synthesis to Biochemical Characterization
Published on: April 3, 2014
Pyridinium Boranephosphonate Modified DNA Oligonucleotides
Subhadeep Roy1, Sibasish Paul1, Mithun Roy2
1Department of Chemistry and Biochemistry, University of Colorado , Boulder, Colorado 80303, United States.
Abstract:
The synthesis of previously unknown derivatives of boranephosphonate that contain amine substitutions at boron and the incorporation of these derivatives into the backbone of DNA oligonucleotides is described. These derivatives result from iodine-mediated replacement of one BH3 hydride of a boranephosphonate linkage by pyridine, various substituted pyridines, other aromatic amines, and certain unsaturated amines. Oligonucleotides containing these backbone modifications show enhanced uptake, relative to unmodified DNA, in mammalian cells. The redox behavior of the boranephosphonate and pyridinium boranephosphonate conjugated linkages has also been studied.
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