Synthesis and properties of a novel artificial nucleoside that acts as a redox switch.
Oligonucleotide that can reversibly alter the duplex-forming ability in response to an external factor has potential to be applied to various genome technologies, e.g. antisense and gene diagnosis technology. A novel bridged nucleoside which is capable of sensing an oxidant and reductant was designed and synthesized. The nucleoside formed a disulfide bridge between C2' and C4' positions, which would enhance its duplex-forming ability under oxidative conditions. Contrastingly, the disulfide bridge was cleaved under reductive conditions; it could cause decrease of duplex-forming ability.
Baba
Takeshi
T
Graduate School of Pharmaceutical Sciences, Osaka University, Suita, Osaka 565-0871, Japan.
Kodama
Tetsuya
T
Imanishi
Takeshi
T
Obika
Satoshi
S
D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry*; D016877:Oxidants / Q000032:analysis; D010084:Oxidation-Reduction; D019163:Reducing Agents / Q000032:analysis; D013936:Thymidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D009705:Nucleosides; D016877:Oxidants; D019163:Reducing Agents; D013936:Thymidine