title: Syntheses of 5-formyl- and 5-carboxyl-dC containing DNA oligos as potential oxidation products of 5-hydroxymethylcytosine in DNA.
abstract: 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 NaBH(4) 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.
authors.affiliation: Department of Chemistry and Institute for Biophyscial Dynamics, The University of Chicago, 929 East 57th Street, Chicago, Illinois 60637, USA. daiqing@uchicago.edu
authors.forename: Qing
authors.initials: Q
authors.lastname: Dai
authors.forename: Chuan
authors.initials: C
authors.lastname: He
mesh_terms: D044503:5-Methylcytosine / Q000031:analogs & derivatives; D003596:Cytosine / Q000031:analogs & derivatives* / Q000737:chemistry; D004247:DNA / Q000138:chemical synthesis* / Q000737:chemistry; D003841:Deoxycytidine / Q000031:analogs & derivatives* / Q000737:chemistry; D008745:Methylation; D015394:Molecular Structure; D009841:Oligonucleotides / Q000138:chemical synthesis*; D010084:Oxidation-Reduction
chemical_list: D009841:Oligonucleotides; D003841:Deoxycytidine; C011865:5-hydroxymethylcytosine; D044503:5-Methylcytosine; D003596:Cytosine; D004247:DNA