Synthesis and chemical properties of a novel 2',4'-bridged nucleic acid analogue with a seven-membered cyclic carbamate structure.
BNA We designed and synthesized a novel bridged nucleic acid (BNA) with N-type sugar conformation, possessing a seven-membered cyclic carbamate structure (2',4'-(CNC) monomer). The monomer shows interesting chemical properties, such as prompt migration of the carbamate bridge from the 2'-to the 3'-position and consequent conformational change of the furanose moiety. These chemical behaviors of 2',4'-BNA(CNC) were investigated by (1)H-NMR analysis, and the structure of the compound after migration was confirmed by X-ray crystallographic analysis.
Nishida
Masaru
M
Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan.
Kodama
Tetsuya
T
Obika
Satoshi
S
Imanishi
Takeshi
T
D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002236:Carbohydrate Conformation; D019906:Nuclear Magnetic Resonance, Biomolecular; D013936:Thymidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D001952:Bridged-Ring Compounds; D013936:Thymidine