Work

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

Year: 2019

Type: article

Abstract: 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.

Source: Organic Letters

DOI: 10.1021/acs.orglett.9b02042

Authors: Sam Kavoosi, Debasis Dey, Kabirul Islam

Institution: University of Pittsburgh

Language: English

Topic: DNA and Nucleic Acid Chemistry

Subfield: Molecular Biology

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

Open Access status: green

Funders: University of Pittsburgh, National Natural Science Foundation of China, National Institute of General Medical Sciences

Awards: G2089435033, Site-Specific Photochemistry on Epigenetic Readers for Interactome Profiling