457067-99-1Relevant academic research and scientific papers
Synthesis and properties of trans-3′,4′-bridged nucleic acids having typical S-type sugar conformation
Sekiguchi, Mitsuaki,Obika, Satoshi,Harada, Yasuki,Osaki, Tomohisa,Somjing, Roongjang,Mitsuoka, Yasunori,Shibata, Nao,Masaki, Miyuki,Imanishi, Takeshi
, p. 1306 - 1316 (2007/10/03)
The synthesis of nucleoside analogues with a conformationally restricted sugar moiety is of great interest. The present research describes the synthesis of BNA (bridged nucleic acid) monomers 1 and 2 bearing a 4,7-dioxabicyclo[4.3.0] nonane skeleton and a methoxy group at the C2' position. Conformational analysis showed that the sugar moiety of these monomers is restricted in a typical S-type conformation. It was difficult to synthesize the phosphoramidite derivative of the ribo-type monomer 1, while the phosphoramidite of the arabino-type monomer 2 was successfully prepared and incorporated into oligodeoxynucleotides (ODNs). The hybridization ability of the obtained ODN derivatives containing 2 with complementary strands was evaluated by melting temperature (Tm) measurements. As a result, the ODN derivatives hybridized with DNA and RNA complements in a sequence-selective manner, though the stability of the duplexes was lower than that of the corresponding natural DNA/DNA or DNA/RNA duplex.
3′-C-branched LNA-type nucleosides locked in an N-type furanose ring conformation: Synthesis, incorporation into oligocleoxynucleotides, and hybridization studies
Meldgaard, Michael,Hansen, Flemming Gundorph,Wengel, Jesper
, p. 6310 - 6322 (2007/10/03)
Three protected 3′-C-branched LNA-type phosphoramidite building blocks 17, 27, and 38, containing furanose rings locked in an N-type conformation, were synthesized from a known 3-C-allyl allofuranose derivative using strategies relying on the introduction
A ring-closing metathesis based synthesis of bicyclic nucleosides locked in S-type conformations by hydroxyl functionalised 3′,4′-trans linkages
Freitag, Morten,Thomasen, Helena,Christensen, Nanna K.,Petersen, Michael,Nielsen, Poul
, p. 3775 - 3786 (2007/10/03)
A [4.3.0]bicyclic nucleoside that contains an unsaturated hydroxylated 3′,4′-trans linkage has been efficiently synthesised. Thus, from diacetone-D-glucose as the starting material, stereoselective Grignard reactions for the introduction of allyl groups,
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.
Synthesis and conformation of a novel bridged nucleoside with S-type sugar puckering, trans-3′,4′-BNA monomer
Obika, Satoshi,Sekiguchi, Mitsuaki,Osaki, Tomohisa,Shibata, Nao,Masaki, Miyuki,Hari, Yoshiyuki,Imanishi, Takeshi
, p. 4365 - 4368 (2007/10/03)
A novel bridged nucleoside bearing a 4,7-dioxabicyclo[4.3.0]nonane skeleton, trans-3′,4′-BNA monomer, was successfully synthesized. A 1H NMR experiment and an X-ray crystallographic analysis revealed that the sugar puckering of the 3′,4′-BNA monomer was restricted to an S-type (C3′-exo) conformation.
3′,4′-trans-Linked bicyclic nucleosides locked in S-type conformations
Thomasen, Helena,Meldgaard, Michael,Freitag, Morten,Petersen, Michael,Wengel, Jesper,Nielsen, Poul
, p. 1888 - 1889 (2007/10/03)
A novel class of 3′,4′-trans-linked bicyclic nucleosides with locked S-type furanose conformations is introduced by synthesis of two model derivatives; one was obtained by cyclic ether formation and the other by ring-closing metathesis methodology.
