title: Hydroxyl-functionalized DNA: an efficient orthogonal protecting strategy and duplex stability.
abstract: Tert-butyldiphenylsilyl (TBDPS) was found to be an effective orthogonal protecting strategy for the 5-substituted hydroxyl groups of de novo synthesized deoxyuridine analogues 1-3 and 7-(3-hydroxypropynyl)- of 8-aza-7-deazadeoxyadenosine 4 for their incorporation into oligodeoxynucleotides by phosphoramidite chemistry. It could be completely cleaved under normal and ultra-mild deprotection conditions applied to DNA synthesis, without extra cleaving operation. The new phosphoramidites were coupled as usual with high yields. The new modified oligodeoxynucleotides were characterized by MALDI-TOF and enzymatic cleavage analysis. The thermal stability and conformation of these hydroxyl-functionalized DNA duplexes were evaluated.
authors.affiliation: School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang, China.
authors.forename: Di
authors.initials: D
authors.lastname: Zhang
authors.forename: Liang
authors.initials: L
authors.lastname: Xu
authors.forename: Xia
authors.initials: X
authors.lastname: Wei
authors.forename: Yaming
authors.initials: Y
authors.lastname: Li
authors.forename: Junlin
authors.initials: J
authors.lastname: He
authors.forename: Keliang
authors.initials: K
authors.lastname: Liu
mesh_terms: D004247:DNA / Q000138:chemical synthesis* / Q000737:chemistry; D006878:Hydroxides / Q000737:chemistry*; D009690:Nucleic Acid Conformation; D009691:Nucleic Acid Denaturation; D017646:Organosilicon Compounds / Q000737:chemistry; D013696:Temperature
chemical_list: D006878:Hydroxides; D017646:Organosilicon Compounds; C009660:t-butyldimethylsilyl compounds; D004247:DNA