ol9b02042_si_001.pdf (2.28 MB)
Synthesis of 5‑Dihydroxyboryluridine Phosphoramidite and Its Site-Specific Incorporation into Oligonucleotides for Probing Thymine DNA Glycosylase
journal contribution
posted on 2019-08-23, 22:15 authored by Sam Kavoosi, Debasis Dey, Kabirul IslamA concise synthetic
strategy to 5-dihydroxyboryldexoyuridine (5boU)
phosphoramidite has been developed. 5boU was introduced into short
oligonucleotides in a site-specific manner, demonstrating compatibility
of the boronic acid moiety with standard solid-phase DNA synthesis
chemistry. Electrophilic 5boU DNAs inhibited thymine DNA glycosylase, a cancer-relevant
DNA-modifying enzyme. We envisage diverse applications of 5boU in
organic synthesis, medicinal chemistry, and chemical biology.