200435-92-3Relevant articles and documents
Chemoenzymatic convergent synthesis of 2'-o,4'-c-methyleneribonucleosides
Sharma, Vivek K.,Kumar, Manish,Olsen, Carl E.,Prasad, Ashok K.
supporting information, p. 6336 - 6341 (2014/07/21)
Novozyme-435-catalyzed efficient regioselective acetylation of one of the two diastereotopic hydroxymethyl functions in 3-O-benzyl-4-C-hydroxymethyl-1,2- O-isopropylidene-α-d-ribofuranose has been achieved. The enzymatic methodology has been successfully
Synthesis of 2′-O,4′-C-alkylene-bridged ribonucleosides and their evaluation as inhibitors of HCV NS5B polymerase
Chapron, Christopher,Glen, Rebecca,La Colla, Massimiliano,Mayes, Benjamin A.,McCarville, Joseph F.,Moore, Stephen,Moussa, Adel,Sarkar, Ruhul,Seifer, Maria,Serra, Ilaria,Stewart, Alistair
supporting information, p. 2699 - 2702 (2014/06/09)
The synthesis of 2′-O,4′-C-methylene-bridged bicyclic guanine ribonucleosides bearing 2′-C-methyl or 5′-C-methyl modifications is described. Key to the successful installation of the methyl functionality in both cases was the use of a one-pot oxidation-Grignard procedure to avoid formation of the respective unreactive hydrates prior to alkylation. The 2′-C-methyl- and 5′-C-methyl-modified bicyclic guanosines were evaluated, along with the known uracil-, cytosine-, adenine-, guanine-LNA and guanine-ENA nucleosides, as potential antiviral agents and found to be inactive in the hepatitis C virus (HCV) cell-based replicon assay. Examination of the corresponding nucleoside triphosphates, however, against the purified HCV NS5B polymerase indicated that LNA-G and 2′-C-methyl-LNA-G are potent inhibitors of both 1b wild type and S282T mutant enzymes in vitro. Activity was further demonstrated for the LNA-G-triphosphate against HCV NS5B polymerase genotypes 1a, 2a, 3a and 4a. A phosphorylation by-pass prodrug strategy may be required to promote anti-HCV activity in the replicon assay.
BASE MODIFIED BICYCLIC NUCLEOSIDES AND OLIGOMERIC COMPOUNDS PREPARED THEREFROM
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, (2013/03/26)
Provided herein are novel base modified bicyclic nucleosides, oligomeric compounds prepared therefrom and methods of using the oligomeric compounds. More particularly, novel pyrimidine bicyclic nucleosides are provided wherein each pyrimidine base is subs
Optimized synthesis of LNA uracil nucleosides
Santhosh Kumar,Kumar, Pawan,Sharma, Pawan K.,Hrdlicka, Patrick J.
supporting information; experimental part, p. 7168 - 7170 (2009/04/10)
A short, very high yielding, and practical synthesis of LNA uracil diol 6 has been developed from the easily accessible glycosyl donor 1. The concluding O3′-debenzylation of 5 resulted in significant reduction of the uracil moiety with many typical debenz
IMPROVED SYNTHESIS OF ?2.2.1|BICYCLO NUCLEOSIDES
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Page/Page column 16; 39, (2008/06/13)
A synthesis of [2.2.1]bicyclo nucleosides which is shorter and provides higher overall yields proceeds via the key intermediate of the general formula III, wherein R4 and R5 are, for instance, sulfonates and R7 is, for instance, a halogen or an acetate. F
Bicyclonucleoside and oligonucleotide analogue
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, (2008/06/13)
An oligo- or polynucleotide analogue having one or more structures of the general formula where B is a pyrimidine or purine nucleic acid base, or an analogue thereof, is disclosed. The use of this analogue provides an oligonucleotide analogue antisense molecule, which is minimally hydrolyzable with an enzyme in vivo, has a high sense strand binding ability, and is easily synthesized.
Novel bicyclonucleoside and oligonucleotide analogue
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, (2008/06/13)
An oligo- or polynucleotide analogue having one or more structures of the general formula where B is a pyrimidine or purine nucleic acid base, or an analogue thereof, is disclosed. The use of this analogue provides an oligonucleotide analogue antisense molecule, which is minimally hydrolyzable with an enzyme in vivo, has a high sense strand binding ability, and is easily synthesized.
2'-O,4'-C-Methylene bridged nucleic acid (2',4'-BNA): synthesis and triplex-forming properties.
Obika,Uneda,Sugimoto,Nanbu,Minami,Doi,Imanishi
, p. 1001 - 1011 (2007/10/03)
For development of ideal antisense and antigene molecules, various chemical modifications of oligonucleotides have been studied. However, despite their importance, there is only limited information available on the triplex-forming ability of the conformat
Bicyclonucleoside and oligonucleotide analogues
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, (2008/06/13)
An oligo- or polynucleotide analogue having one or more structures of the general formula where B is a pyrimidine or purine nucleic acid base, or an analogue thereof, is disclosed. The use of this analogue provides an oligonucleotide analogue antisense molecule, which is minimally hydrolyzable with an enzyme in vivo, has a high sense strand binding ability, and is easily synthesized.
DNA triplex structures are stabilized by the incorporation of 3'-endo blocked pyrimidine nucleosides in the hoogsteen strand
Savy, Pascal,Benhida, Rachid,Fourrey, Jean-Louis,Maurisse, Rosalie,Sun, Jian-Sheng
, p. 2287 - 2289 (2007/10/03)
A short route to pyrimidine locked nucleosides has been developed for their incorporation in triplex forming oligonucleotides (TFO). Compared to oligonucleotides built with standard nucleosides, the modified TFOs containing 3'-endo blocked residues formed