Synthesis and hydrolysis of oligodeoxyribonucleotides containing 2-aminopurine.
A new method is reported for the synthesis of oligodeoxyribonucleotides containing 2-aminopurine residues at selected sites. This method involves protection of the 2-aminopurine ribonucleoside, reduction to the deoxyribonucleoside and standard preparation of the 5'-0- (4,4'-dimethoxytrityl)-3'-O-(2-cyanoethyl)-N,N- diisopropylphosphoramidite. The 2-aminopurine phosphoramidite prepared by this method couples with high efficiency and is stable under standard automated synthesis conditions. The presence and location of the 2-aminopurine residue is easily verified by treatment of the oligodeoxyribonucleotide with hot piperidine. The mechanism for selective hydrolysis of the 2-aminopurine residue in alkaline solution is predominantly direct cleave of the glycosidic bond.
Fujimoto
J
J
Division of Pediatrics, City of Hope National Medical Center, Duarte, CA 91010, USA.
Nuesca
Z
Z
Mazurek
M
M
Sowers
L C
LC
D015075:2-Aminopurine; D001483:Base Sequence; D006868:Hydrolysis; D008969:Molecular Sequence Data; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000378:metabolism
D009838:Oligodeoxyribonucleotides; D015075:2-Aminopurine