Synthesis and properties of a 2'-deoxy analogue of trans-3',4'-BNA with an S-type sugar conformation.
We previously synthesized bridged nucleic acid (BNA) analogues possessing an S-type sugar conformation. Recently, we achieved the synthesis of a 2'-deoxy analogue of trans-3',4'-BNA. The structure of this compound was confirmed by X-ray crystallography, which indicated that its sugar ring had an S-type conformation. The hybridization ability of the 2'-deoxy-trans-3',4'-BNA-modified oligonucleotide with DNA and RNA complements was evaluated, and it was found that 2'-deoxy-trans-3',4'-BNA showed superior hybridization ability compared with other BNA analogues with S-type sugar conformation.
Sugaya
Kensaku
K
Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan.
Harada
Yasuki
Y
Mitsuoka
Yasunori
Y
Osaki
Tomohisa
T
Obika
Satoshi
S
Kodama
Tetsuya
T
Imanishi
Takeshi
T
D001952:Bridged-Ring Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D002236:Carbohydrate Conformation; D004247:DNA / Q000737:chemistry; D009693:Nucleic Acid Hybridization; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry*; D009841:Oligonucleotides / Q000737:chemistry*; D012313:RNA / Q000737:chemistry; D013936:Thymidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D001952:Bridged-Ring Compounds; D009705:Nucleosides; D009841:Oligonucleotides; D012313:RNA; D004247:DNA; D013936:Thymidine