Synthesis and properties of a novel bridged nucleic acid analogue bearing a P3'-->N5' phosphoroamidate linkage, 5'-amino-3', 5'-BNA.
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.
Sekiguchi
Mitsuaki
M
Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan.
Obika
Satoshi
S
Somjing
Roonjang
R
Imanishi
Takeshi
T
D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry*; D018076:DNA, Complementary / Q000737:chemistry; D009692:Nucleic Acid Heteroduplexes / Q000138:chemical synthesis / Q000737:chemistry; D009696:Nucleic Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D010756:Phosphoric Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D018075:RNA, Complementary / Q000737:chemistry; D044366:Transition Temperature
C521139:5'-amino-3',5'-BNA; D000577:Amides; D018076:DNA, Complementary; D009692:Nucleic Acid Heteroduplexes; D009696:Nucleic Acids; D010756:Phosphoric Acids; D018075:RNA, Complementary; C011067:phosphoramidic acid