title: Synthesis and hydrolysis of oligodeoxyribonucleotides containing 2-aminopurine.
abstract: 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.
authors.affiliation: Division of Pediatrics, City of Hope National Medical Center, Duarte, CA 91010, USA.
authors.forename: J
authors.initials: J
authors.lastname: Fujimoto
authors.forename: Z
authors.initials: Z
authors.lastname: Nuesca
authors.forename: M
authors.initials: M
authors.lastname: Mazurek
authors.forename: L C
authors.initials: LC
authors.lastname: Sowers
mesh_terms: D015075:2-Aminopurine; D001483:Base Sequence; D006868:Hydrolysis; D008969:Molecular Sequence Data; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000378:metabolism
chemical_list: D009838:Oligodeoxyribonucleotides; D015075:2-Aminopurine