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5-Hydroxymethylcytosine and 5-formylcytosine containing deoxyoligonucleotides: facile syntheses and melting
Shuguang Xuan1, Qiong Wu1, Liang Cui2
1Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore.
Abstract:
An oxidation-based synthetic approach was developed for facile preparation of 5-formyl-2'-deoxycytidine and 5-hydroxymethyl-2'-deoxycytidine phosphoramidites. Upon introducing organic solvent components and copper catalysts, C5-methyl groups of 5-methyl-2'-deoxycytidine and thymidine were readily oxidized to formyl and hydroxyl functionality, respectively. Standard solid phase DNA synthesis and conventional deprotection methods were applicable to synthesize 5-formyl- or 5-hydroxymethyl-cytosine containing DNA oligonucleotides, which were used to study the effect of epigenetic modifications on DNA thermal dynamic stability.
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