Synthesis of novel 2'-deoxy type trans-3',4'-bridged nucleic acid.
We newly designed and synthesized a 2'-deoxy type trans-3',4'-bridged nucleic acid (trans-3',4'-BNA) analogues bearing a 4,7-dioxabicyclo[4.3.0]nonane structure. The synthesis of the trans-3',4'-BNA was carried out successfully from thymidine over 21 steps. The structure of trans-3',4'-BNA was confirmed by x-ray crystallographic analysis, indicating that the furanose ring has a typical S-type conformation with C(3')-exo puckering.
Osaki
Tomohisa
T
Graduate School of Pharmaceutical Sciences, Osaka University, Osaka, Japan.
Obika
Satoshi
S
Harada
Yasuki
Y
Mitsuoka
Yasunori
Y
Sugaya
Kensaku
K
Sekiguchi
Mitsuaki
M
Roongjang
Somjing
S
Imanishi
Takeshi
T
D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis / Q000737:chemistry; D018360:Crystallography, X-Ray; D003853:Deoxyribonucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D015195:Drug Design; D008722:Methods; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
D001643:Bridged Bicyclo Compounds; D003853:Deoxyribonucleosides