Hydroxyl-functionalized DNA: an efficient orthogonal protecting strategy and duplex stability.
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.
Zhang
Di
D
School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang, China.
Xu
Liang
L
Wei
Xia
X
Li
Yaming
Y
He
Junlin
J
Liu
Keliang
K
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
D006878:Hydroxides; D017646:Organosilicon Compounds; C009660:t-butyldimethylsilyl compounds; D004247:DNA