Syntheses of 5-formyl- and 5-carboxyl-dC containing DNA oligos as potential oxidation products of 5-hydroxymethylcytosine in DNA.

Syntheses of 5-formyl- and 5-carboxyl-dC containing DNA oligos as potential oxidation products of 5-hydroxymethylcytosine in DNA.
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DOI:
10.1021/ol201189n
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发表时间:
2011-07-01
期刊:
影响因子:
5.2
通讯作者:
He, Chuan
He, Chuan
中科院分区:
化学1区
文献类型:
--
作者:
Dai, Qing;He, Chuan

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为了研究含5-羟甲基胞嘧啶(5-hmC)的DNA的潜在氧化产物,我们合成了5-甲酰基和5-甲氧羰基-2 ′-脱氧胞苷亚磷酰胺。III中的5-甲酰基易于引入,并且与亚磷酰胺和DNA合成相容。用NaBH 4对ODN 1进行额外处理,定量产生了相应的ODN 2。亚磷酰胺V也被掺入DNA中,并且甲酯可以在温和的碱性条件下水解,得到ODN 3。
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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