Synthesis of 5‑Dihydroxyboryluridine Phosphoramidite
and Its Site-Specific Incorporation into Oligonucleotides for Probing
Thymine DNA Glycosylase
Version 2 2019-08-26, 19:10
Version 1 2019-08-23, 22:15
Posted on 2019-08-26 - 19:10
A 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.
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Kavoosi, Sam; Dey, Debasis; Islam, Kabirul (2019). Synthesis of 5‑Dihydroxyboryluridine Phosphoramidite
and Its Site-Specific Incorporation into Oligonucleotides for Probing
Thymine DNA Glycosylase. ACS Publications. Collection. https://doi.org/10.1021/acs.orglett.9b02042
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