Synthesis and properties of a novel bridged nucleic acid analogue bearing a P3'->N5' phosphoroamidate linkage, 5'-amino-3', 5'-BNA | Zendy

Masahito Sekiguchi | Zendy

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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

Author(s) -

Masahito Sekiguchi

Publication year - 2004

Publication title -

nucleic acids symposium series

Language(s) - English

Resource type - Journals

eISSN - 1746-8272

pISSN - 0261-3166

DOI - 10.1093/nass/48.1.7

Subject(s) - phosphoramidate , nucleic acid , oligonucleotide , chemistry , amino acid , dihedral angle , stereochemistry , linkage (software) , combinatorial chemistry , biochemistry , dna , organic chemistry , hydrogen bond , molecule , gene

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 degrees. 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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