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Nucleic Acids Symposium Series 2004 48(1):7-8; doi:10.1093/nass/48.1.7
© 2004 by Oxford University Press
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Synthesis and properties of a novel bridged nucleic acid analogue bearing a P3'->N5' phosphoroamidate linkage, 5'-amino-3', 5'-BNA

Mitsuaki Sekiguchi, Satoshi Obika, Roonjang Somjing and Takeshi Imanishi

Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan

We have designed and successfully synthesized a novel bridged nucleic acid analogue with a P3'->N5' phosphoramidate linkage, 5'-amino-3',5'-BNA. X-ray crystallographic analysis demonstrated that the 5'-amino-3',5'-BNA had C1-exo-O4-endo sugar puckering and a constrained {gamma} dihedral angle of 22.8°. The oligonucleotides containing 5'-amino-3',5'-BNA exhibited strong binding affinity towards complementary strands. In addition, the 5'-amino-3',5'-BNA oligonucleotide was easily hydrolyzed at its phosphoramidate linkage under mild acidic conditions.


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