Synthesis and properties of a novel bridged nucleic acid analogue, 5'-amino-3',5'-BNA.
An oligonucleotide P3'-->N5' phosphoramidate (5'-amino-DNA) attracts much attention because of its potential for application to DNA sequencing; however, its ability to hybridize with complementary strands is low. To overcome this drawback of the 5-amino-DNA, we have designed and successfully synthesized a novel nucleic acid analogue having a P3'-->N5' phosphoramidate linkage and a constrained sugar moiety, 5'-amino-3'-C,5'-N-methylene bridged nucleic acid (5'-amino-3',5'-BNA). The binding affinity of the 5'-amino-3',5'-BNA towards complementary DNA and RNA strands was investigated by UV melting experiments. The melting temperature (Tm) of the duplex comprising the 5'-amino-3',5'-BNA and its complementary strand was much higher than that of the duplex containing the corresponding 5-amino-DNA.
Sekiguchi
Mitsuaki
M
Graduate School of Pharmaceutical Sciences, Osaka University, Osaka, Japan.
Obika
Satoshi
S
Somjing
Roongjang
R
Imanishi
Takeshi
T
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D004247:DNA / Q000737:chemistry; D018076:DNA, Complementary / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D009690:Nucleic Acid Conformation; D009693:Nucleic Acid Hybridization; D009696:Nucleic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D009841:Oligonucleotides / Q000737:chemistry; D016376:Oligonucleotides, Antisense / Q000737:chemistry; D012313:RNA / Q000737:chemistry; D018075:RNA, Complementary / Q000378:metabolism; D017422:Sequence Analysis, DNA; D013696:Temperature; D014466:Ultraviolet Rays
D019086:Bridged Bicyclo Compounds, Heterocyclic; D018076:DNA, Complementary; D009696:Nucleic Acids; D009841:Oligonucleotides; D016376:Oligonucleotides, Antisense; D018075:RNA, Complementary; D012313:RNA; D004247:DNA