Synthesis of 5-Dihydroxyboryluridine Phosphoramidite and Its Site-Specific Incorporation into Oligonucleotides for Probing Thymine DNA Glycosylase

摘要

A concise synthetic strategy to 5-dihydroxyboryldexoyuridine (SboU) phosphoramidite has been developed. SboU 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 SboU DNAs inhibited thymine DNA glycosylase, a cancer-relevant DNA-modifying enzyme. We envisage diverse applications of SboU in organic synthesis, medicinal chemistry, and chemical biology.