title: 5-Hydroxymethylcytosine and 5-formylcytosine containing deoxyoligonucleotides: facile syntheses and melting temperature studies.
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.
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore.
authors.forename: Shuguang
authors.initials: S
authors.lastname: Xuan
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore.
authors.forename: Qiong
authors.initials: Q
authors.lastname: Wu
authors.affiliation: Interdisciplinary Research Group in Infectious Diseases, Singapore-MIT Alliance for Research & Technology (SMART), Singapore.
authors.forename: Liang
authors.initials: L
authors.lastname: Cui
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore.
authors.forename: Dawei
authors.initials: D
authors.lastname: Zhang
authors.affiliation: Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore. Electronic address: fwshao@ntu.edu.sg.
authors.forename: Fangwei
authors.initials: F
authors.lastname: Shao
mesh_terms: D044503:5-Methylcytosine / Q000031:analogs & derivatives; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D056148:Chromatography, Reverse-Phase; D003300:Copper / Q000737:chemistry; D003596:Cytosine / Q000031:analogs & derivatives* / Q000737:chemistry; D009841:Oligonucleotides / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D010084:Oxidation-Reduction; D044366:Transition Temperature
chemical_list: C560973:5-formylcytosine; D009841:Oligonucleotides; C011865:5-hydroxymethylcytosine; D044503:5-Methylcytosine; D003300:Copper; D003596:Cytosine
keywords: 5-Formlycytosine; 5-Hydroxymethylcytosine; Melting temperature; Oligonucleotide synthesis