- C6–O-alkylated 7-deazainosine nucleoside analogues: Discovery of potent and selective anti-sleeping sickness agents
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African trypanosomiasis, a deadly infectious disease caused by the protozoan Trypanosoma brucei spp., is spread to new hosts by bites of infected tsetse flies. Currently approved therapies all have their specific drawbacks, prompting a search for novel th
- Hulpia, Fabian,Bouton, Jakob,Campagnaro, Gustavo D.,Alfayez, Ibrahim A.,Mabille, Dorien,Maes, Louis,de Koning, Harry P.,Caljon, Guy,Van Calenbergh, Serge
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- SYNTHESIS AND STRUCTURE OF HIGH POTENCY RNA THERAPEUTICS
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This invention provides expressible polynucleotides, which can express a target protein or polypeptide. Synthetic mRNA constructs for producing a protein or polypeptide can contain one or more 5′ UTRs, where a 5′ UTR may be expressed by a gene of a plant. In some embodiments, a 5′ UTR may be expressed by a gene of a member of Arabidopsis genus. The synthetic mRNA constructs can be used as pharmaceutical agents for expressing a target protein or polypeptide in vivo.
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- Synthesis of Nucleosides through Direct Glycosylation of Nucleobases with 5-O-Monoprotected or 5-Modified Ribose: Improved Protocol, Scope, and Mechanism
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Simplifying access to synthetic nucleosides is of interest due to their widespread use as biochemical or anticancer and antiviral agents. Herein, a direct stereoselective method to access an expansive range of both natural and synthetic nucleosides up to a gram scale, through direct glycosylation of nucleobases with 5-O-tritylribose and other C5-modified ribose derivatives, is discussed in detail. The reaction proceeds through nucleophilic epoxide ring opening of an in situ formed 1,2-anhydrosugar (termed “anhydrose”) under modified Mitsunobu reaction conditions. The scope of the reaction in the synthesis of diverse nucleosides and other 1-substituted riboside derivatives is described. In addition, a mechanistic insight into the formation of this key glycosyl donor intermediate is provided.
- Downey, A. Michael,Pohl, Radek,Roithová, Jana,Hocek, Michal
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supporting information
p. 3910 - 3917
(2017/03/27)
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- Phosphazole compounds
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A class of substituted and unsubstituted nucleo-base analogs and related azoles, designated as "phosphazoles," is disclosed, certain preferred embodiments having the basic structure of STR1 Also disclosed are methods of making and using the new compounds.
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- A facile and improved synthesis of tubercidin and certain related pyrrolo[2,3-d]pyrimidine nucleosides by the stereospecific sodium salt glycosylation procedure [1]
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A simple synthesis of tubercidin, 7-deazaguanosine and 2'-deoxy-7-deazaguanosine has been accomplished using the sodium salt glycosylation procedure. Reaction of the sodium salt of 4-chloro- and 2-amino-4-chloro-pyrrolo[2,3-d]pyrimidine, 3 and 4, respectively, with 1-chloro-2,3-O-isopropylidene,5-O-(t-butyl)dimethylsilyl-α-D-ribofur nose gave the corresponding protected nucleosides 6 and 7 with β-anomeric configuration. Deprotection of 6 provided 8, which on heating with methanolic ammonia gave tubercidin in excellent yield. Functional group transformation of 7, followed by deisopropylidenation gave 2-aminotubercidin and 2-amino-7-β-ribofuranosylpyrrolo[2,3-d]pyrimidine-4(3H)-thione. Treatment of 7 with 1N sodium methoxide followed by exposure to aqueous trifluoroacetic acid, and ether cleavage furnished 7-deazaguanosine. 2'-Deoxy-7-deazaguanosine and 2'-deoxy-7-deaza-6-thioguanosine were also prepared by using similar sequence of reactions employing 4 and 1-chloro-2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranose.
- Ramasamy,Imamura,Robins,Revankar
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p. 1893 - 1898
(2007/10/02)
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- Synthesis of 2-Amino-3,7-dihydro-7-(β-D-ribofuranosyl)-4H-pyrrolopyrimindin-4-one - 7-Deazaguanosine - the Parent Compound of the Nucleoside Q
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2-Amino-3,7-dihydro-7-(β-D-ribofuranosyl)-4H-pyrrolopyrimidin-4-one (1a), the parent compound of the rare nucleoside Q, has been synthesized using the pyrrolopyrimidine derivative 3a which was available by phase transfer glycosylation.N-3 al
- Seela, Frank,Hasselmann, Doris
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p. 3395 - 3402
(2007/10/02)
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