Acid-mediated cleavage of oligonucleotide P3' --> N5' phosphoramidates triggered by sequence-specific triplex formation |
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Authors: | Obika Satoshi Tomizu Masaharu Negoro Yoshinori Osaki Tomohisa Orita Ayako Ueyama Yuji Nakagawa Osamu Imanishi Takeshi |
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Affiliation: | Graduate School of Pharmaceutical Sciences, Osaka University, Osaka, Japan. |
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Abstract: | The P-N bond in oligonucleotide P3' --> N5' phosphoramidates (5'-amino-DNA) is known to be chemoselectively cleaved under mild acidic conditions. We prepared homopyrimidine oligonucleotides containing 5'-amino-5'-deoxythymidine (5'-amino-DNA thymine monomer) or its conformationally locked congener, 5'-amino-2',4'-BNA thymine monomer, at midpoint of the sequence. The effect of triplex formation with homopurineohomopyrimidine dsDNA targets on acid-mediated hydrolysis of the P3' --> N5' phosphoramidate linkage was evaluated. Very interestingly, it was found that the triplex formation significantly accelerates the P-N bond cleavage. |
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