Journal
ORGANIC LETTERS
Volume 13, Issue 13, Pages 3446-3449Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol201189n
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Funding
- NIH [GM071440, GM088599]
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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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