title: Syntheses of two 5-hydroxymethyl-2'-deoxycytidine phosphoramidites with TBDMS as the 5-hydroxymethyl protecting group and their incorporation into DNA.
abstract: 5-Hydroxymethylcytosine (5-hmC) is a newly discovered DNA base modification in mammalian genomic DNA that is proposed to be a major epigenetic mark. We report here the syntheses of two new versions of phosphoramidites III and IV from 5-iodo-2'-deoxyuridine in 18% and 32% overall yields, respectively, with TBDMS as the 5-hydroxyl protecting group. Phosphoramidites III and IV allow efficient incorporation of 5-hmC into DNA and a "one-step" deprotection procedure to cleanly remove all the protecting groups. A "two-step" deprotection strategy is compatible with ultramild DNA synthesis, which enables the synthesis of 5hmC-containing DNA with additional modifications.
authors.affiliation: Department of Chemistry, The University of Chicago, 929 E. 57th St., Chicago, Illinois, 60637 United States. daiqing@uchicago.edu
authors.forename: Qing
authors.initials: Q
authors.lastname: Dai
authors.forename: Chun-Xiao
authors.initials: CX
authors.lastname: Song
authors.forename: Tao
authors.initials: T
authors.lastname: Pan
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*; D009943:Organophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D012833:Siloxanes / Q000737:chemistry*; D013343:Styrenes / Q000737:chemistry*
chemical_list: C506477:4-(tert-butyldimethylsiloxy)styrene; D009943:Organophosphorus Compounds; D012833:Siloxanes; D013343:Styrenes; C434331:phosphoramidite; C011865:5-hydroxymethylcytosine; D044503:5-Methylcytosine; D003596:Cytosine; D004247:DNA