Syntheses of 5-Formyl- and 5-Carboxyl-dC Containing DNA Oligos as Potential Oxidation Products of 5-Hydroxymethylcytosine in DNA

被引：33

作者：

Dai, Qing ^{[1
]}

He, Chuan

机构：

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

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 13期

关键词：

CONVERSION;

D O I：

10.1021/ol201189n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

To investigate the potential oxidation products of 5-hydroxymethylcytosine (5-hmC)-containing DNA, we present here efficient syntheses of 5-formyl- and 5-methoxycarbonyl-2'-deoxycytidine phosphoramidites. The 5-formyl group in III was easy to introduce and was compatible with phosphoramidite and DNA syntheses. An additional treatment of ODN1 with NaBH4 produced the corresponding ODN2 quantitatively. Phosphoramidite V was also incorporated into DNA, and the methyl ester could be hydrolyzed under mild basic conditions to afford ODN3.

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页码：3446 / 3449

页数：4

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