Synthesis of 5-Dihydroxyboryluridine Phosphoramidite and Its Site-Specific Incorporation into Oligonucleotides for Probing Thymine DNA Glycosylase.
Synthesis of 5-Dihydroxyboryluridine Phosphoramidite and Its Site-Specific Incorporation into Oligonucleotides for Probing Thymine DNA Glycosylase.
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DOI：
10.1021/acs.orglett.9b02042
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发表时间：
2019-08
期刊：
影响因子：
5.2
通讯作者：
Sam Kavoosi;D. Dey;K. Islam
中科院分区：
文献类型：
--
作者：
Sam Kavoosi;D. Dey;K. Islam
介绍了一种合成5-二羟基硼基右尿嘧啶（5boU）磷酰胺的简便方法。5boU以特定位点的方式被引入短寡核苷酸中，证明了硼酸部分与标准固相DNA合成化学的相容性。亲电性5boU DNA抑制胸腺嘧啶DNA糖基化酶，这是一种与癌症相关的DNA修饰酶。我们设想5boU在有机合成，药物化学和化学生物学中的多种应用。
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.