Synthesis of 5-formyl-2'-deoxyuridine and its incorporation into oligodeoxynucleotides.
A straightforward, efficient method for the synthesis of 5-formyl-2'-deoxyuridine (dfU) and solid-phase synthesis of oligodeoxynucleotides containing dfU using a phosphoramidite method are described. The synthesis of dfU is achieved by oxidation of the 5-methyl group in thymidine derivatives. However, incorporation of the dfU 3'-O-phosphoramidite into oligodeoxynucleotides proceeds in low yield, due to instability of the 5-formyl group under conditions used for automated DNA synthesis. Therefore, oligodeoxynucleotides containing a 5-(1,2-dihydroxyethyl)uracil derivative are first prepared and finally oxidized by periodate to give the desired oligodeoxynucleotides containing 5-formyluracil.
Sato
Kousuke
K
Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo, Japan.
Hirose
Wataru
W
Matsuda
Akira
A
D001709:Biotechnology / Q000379:methods; D019411:Clinical Laboratory Techniques; D003857:Deoxyuridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis*; D009943:Organophosphorus Compounds; D010084:Oxidation-Reduction; D013936:Thymidine / Q000737:chemistry
D009838:Oligodeoxyribonucleotides; D009943:Organophosphorus Compounds; C434331:phosphoramidite; C061519:5-formyl-2'-deoxyuridine; D013936:Thymidine; D003857:Deoxyuridine