457067-99-1Relevant articles and documents
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.
NUCLEOSIDE ANALOGUES WHOSE SUGAR MOIETIES ARE BOUND IN S-FORM AND OLIGONUCLEOTIDE DERIVATIVES COMPRISING NUCLEOTIDE ANALOGUES THEREOF
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Page 13; 16, (2010/02/09)
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.
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,
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.
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.
