139434-69-8Relevant academic research and scientific papers
LIGAND-2'-MODIFIED NUCLEIC ACIDS, SYNTHESIS THEREOF AND INTERMEDIATE COMPOUNDS THEREOF
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, (2021/03/05)
The present invention relates to methods for synthesizing compounds useful as potent and stable RNA interference agents, derivatives thereof, and intermediates thereto.
Syntheses of prodrug-type 2′-O-methyldithiomethyl oligonucleotides modified at natural four nucleoside residues and their conversions into natural 2′-hydroxy oligonucleotides under reducing condition
Hayashi, Junsuke,Ochi, Yosuke,Morita, Yasuyuki,Soubou, Katsuma,Ohtomo, Yuhei,Nishigaki, Misa,Tochiyama, Yuko,Nakagawa, Osamu,Wada, Shun-ichi,Urata, Hidehito
, p. 5838 - 5844 (2018/11/23)
We previously reported that reducing-environment-responsive prodrug-type small interfering RNA (siRNA) bearing 2′-O-methyldithiomethyl (2′-O-MDTM) uridine exhibits efficient knockdown activity and nuclease resistance. In this report, we describe the prepa
LIGAND-MODIFIED DOUBLE-STRANDED NUCLEIC ACIDS
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Paragraph 00663, (2016/07/05)
The invention provides for double stranded nucleic acid molecules comprising a 5 'extension of the sense or antisense strand and further comprising a plurality of nucleotides that are conjugated to a ligand and methods of using the double-stranded nucleic acid molecules. Ligand-modified oligomers where the sense stands form a tetraloop provide new potent and stable RNA interference agents. These dsNA molecules are synthesized using a plurality of nucleotides that include ligand-modified monomers, nucleotide analog monomers, modified nucleotide monomers and the like, using standard nucleotide synthetic methods and systems.
An azidomethyl protective group in the synthesis of oligoribonucleotides by the phosphotriester method
Efimov,Aralov,Fedunin,Klykov,Chakhmakhcheva
scheme or table, p. 250 - 253 (2010/04/06)
A rapid and effective method of an automatic oligoribonucleotide synthesis alternative to the phosphoramidite one was developed. This method is based on the phosphotriester approach to internucleotide bond formation under intramolecular O-nucleophilic cat
Synthesis of RNA by the rapid phosphotriester method using azido-based 2'-O-protecting groups
Efimov,Aralov,Klykov,Chakhmakhcheva
scheme or table, p. 846 - 865 (2010/08/22)
The azidomethyl and 2-(azidomethyl)benzoyl as 2'-OH protecting groups are reported for preparation of oligoribonucleotides by the phosphotriester solid-phase method using O-nucleophilic intramolecular catalysis. The procedures for the synthesis of the corresponding monomer synthons were developed and the usefulness of the application of 2'-O-azidomethyl and 2'-O-2-(azidomethyl) benzoyl groups was examined in the synthesis of different RNA fragments with a chain length of 15-22 nucleotides. The azidomethyl group was found to be more preferable for effective synthesis of oligoribonucleotides. Hybridization properties of RNAs toward their complementary oligonucleotides were examined before and after the removal of 2'-O-azidomethyl groups.
Assessment of 4-nitrogenated benzyloxymethyl groups for 2′-Hydroxyl protection in solid-phase RNA synthesis
Cieslak, Jacek,Kauffman, Jon S.,Kolodziejski, Michelle J.,Lloyd, John R.,Beaucage, Serge L.
, p. 671 - 674 (2008/02/05)
The search for a 2′-OH protecting group that would impart ribonucleoside phosphoramidites with coupling kinetics and coupling efficiencies comparable to those of deoxyribonucleoside phosphoramidites led to an assessment of 2′-0-(4-nitrogenated benzyloxy)m
Synthesis of RNA using 2′-O-DTM protection
Semenyuk, Andrey,Foeldesi, Andras,Johansson, Tommy,Estmer-Nilsson, Camilla,Blomgren, Peter,Braennvall, Mathias,Kirsebom, Leif A.,Kwiatkowski, Marek
, p. 12356 - 12357 (2007/10/03)
tert-Butyldithiomethyl (DTM), a novel hydroxyl protecting group, cleavable under reductive conditions, was developed and applied for the protection of 2′-OH during solid-phase RNA synthesis. This function is compatible with all standard protecting groups used in oligonucleotide synthesis, and allows for fast and high-yield synthesis of RNA. Oligonucleotides containing the 2′-O-DTM groups can be easily deprotected under the mildest possible aqueous and homogeneous conditions. The preserved 5′-O-DMTr function can be used for high-throughput cartridge RNA purification. Copyright
The S,X-acetals in nucleoside chemistry. I. The synthesis of 2′- and 5′-O-methylthiomethylribonucleosides
Pechenov,Zavgorodny,Shvets,Miroshnikov
, p. 327 - 333 (2007/10/03)
Ribonucleoside 2′- and 5′-O-methylthiomethyl derivatives were synthesized from selectively protected nucleosides by the action of a dimethyl sulfoxide-acetic anhydride-acetic acid mixture.
2'-O-methylthiomethyl modifications in hammerhead ribozymes
Karpeisky, Alexander,Gonzalez, Carolyn,Burgin, Alex B.,Usman, Nassim,Beigelman, Leonid
, p. 955 - 958 (2007/10/03)
The synthesis of all four phosphoramidites of 2'-O-methylthiomethyl ribonucleosides and their incorporation into hammerhead ribozymes and influence on nuclease stability and catalytic activity is described.
