583843-95-2Relevant academic research and scientific papers
Development of a novel nucleoside analogue with S-type sugar conformation: 2′-deoxy-trans-3′,4′-bridged nucleic acids
Osaki, Tomohisa,Obika, Satoshi,Harada, Yasuki,Mitsuoka, Yasunori,Sugaya, Kensaku,Sekiguchi, Mitsuaki,Roongjang, Somjing,Imanishi, Takeshi
, p. 8977 - 8986 (2008/02/10)
Two novel trans-3′,4′-bridged nucleic acid (trans-3′,4′-BNA) monomers, one with a 3,5,8-trioxabicyclo[5.3.0]decane structure and the other with a 4,7-dioxabicyclo[4.3.0]nonane structure, were successfully synthesized from thymidine. The locked trans-fused ring structures of the nucleoside analogues were confirmed by X-ray crystallography, which also indicated that their furanose rings had a typical S-type conformation involving C2′-endo or C3′-exo sugar puckering, respectively, and the same ring conformation as that observed in the B-type helical structure of the DNA duplex.
Synthesis of novel 2′-deoxy type trans-3′,4′-bridged nucleic acid
Osaki, Tomohisa,Obika, Satoshi,Harada, Yasuki,Mitsuoka, Yasunori,Sugaya, Kensaku,Sekiguchi, Mitsuaki,Roongjang, Somjing,Imanishi, Takeshi
, p. 1079 - 1082 (2008/09/17)
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 ste
Synthesis and conformation of a novel bridged nucleic acid having a trans-fused 3,5,8-trioxabicyclo[5.3.0]decane structure
Obika, Satoshi,Osaki, Tomohisa,Sekiguchi, Mitsuaki,Somjing, Roongjang,Harada, Yasuki,Imanishi, Takeshi
, p. 4801 - 4804 (2007/10/03)
A novel bridged nucleic acid analogue, 2′-deoxy-trans-3′, 4′-BNA thymine monomer, was successfully synthesized. An ab initio calculation and X-ray structure analysis revealed that the trans-fused bicyclo[5.3.0]decane structure of the 2′-deoxy-trans-3′,4′-BNA effectively constrained the sugar puckering in C2′-endo with appropriate γ, δ and χ angles.
NUCLEOSIDE ANALOGUES WHOSE SUGAR MOIETIES ARE BOUND IN S-FORM AND OLIGONUCLEOTIDE DERIVATIVES COMPRISING NUCLEOTIDE ANALOGUES THEREOF
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Compounds of the following general formula (1) and salts thereof: where A represents an alkylene group having 1 to 2 carbon atoms, etc.; B represents an aromatic heterocyclic group which may have a substituent, etc.; R1 and R2 each represent a hydrogen atom, a protective group for a hydroxyl group for synthesis of nucleic acid, a phosphate group, or -P(R4)R5 [where R4 and R5 are the same or different, and each represent a hydroxyl group, a hydroxyl group protected with a protective group for synthesis of nucleic acid, a mercapto group, a mercapto group protected with a protective group for synthesis of nucleic acid, etc.]; and R3 represents a hydrogen atom, a halogen atom, a hydroxyl group, a hydroxyl group protected with a protective group for synthesis of nucleic acid, etc. These compounds are useful for producing oligonucleotide analogues useful for the antisense method, antigene method, etc., and for producing their intermediates.
