Syntheses of Two 5-Hydroxymethyl-2′-deoxycytidine Phosphoramidites with TBDMS as the 5-Hydroxymethyl Protecting Group and Their Incorporation into DNA

被引：30

作者：

Dai, Qing ^{[1
]}

Song, Chun-Xiao ^{[1
]}

Pan, Tao ^{[2
]}

He, Chuan ^{[1
]}

机构：

[1] Univ Chicago, Dept Chem, Chicago, IL 60637 USA

[2] Univ Chicago, Dept Biochem & Mol Biol, Chicago, IL 60637 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 10期

关键词：

SOLID-PHASE SYNTHESIS; 5-METHYLCYTOSINE; METHYLATION; CONVERSION;

D O I：

10.1021/jo200566d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

5-Hydroxymethylcytosine (5-hmC) is a newly discovered DNA base modification in mammalian genomic DNA that is proposed to be a major epigenetic mark. We report here the syntheses of two new versions of phosphoramidites III and IV from 5-iodo-2'-deoxyuridine in 18% and 32% overall yields, respectively, with TBDMS as the 5-hydroxyl protecting group. Phosphoramidites III and IV allow efficient incorporation of 5-hmC into DNA and a "one-step" deprotection procedure to cleanly remove all the protecting groups. A "two-step" deprotection strategy is compatible with ultramild DNA synthesis, which enables the synthesis of 5hmC-containing DNA with additional modifications.

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页码：4182 / 4188

页数：7

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