Transglycosylation in the Modification and Isotope Labeling of Pyrimidine Nucleosides.
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DOI: 10.1021/acs.orglett.0c01941
Abstract: Transglycosylation of pyrimidine nucleosides is demonstrated in a one-pot synthesis of uridine derivatives under microwave irradiation. Inductive activation of 2',3',5'-tri-O-acetyl uridine with a 5-nitro group produces a more-reactive glycosyl donor. Under optimized Vorbrüggen conditions, the… read more here.
Keywords: isotope labeling; labeling pyrimidine; pyrimidine; pyrimidine nucleosides ... See more keywords
Pyrimidine Nucleosides Syntheses by Late-Stage Base Heterocyclization Reactions
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DOI: 10.1021/acs.orglett.2c03152
Abstract: An efficient two-step procedure for the syntheses of pyrimidine nucleosides is presented. A series of glycosyl 5-(aminomethylene)-1,3-dioxane-4,6-dione derivatives were prepared from β-anomeric isonitriles by reaction with Meldrum’s acid or by allowing aminomethylene Meldrum’s acid to… read more here.
Keywords: stage base; late stage; base heterocyclization; nucleosides syntheses ... See more keywords
Pyrimidine Nucleosides with a Reactive (β-Chlorovinyl)sulfone or (β-Keto)sulfone Group at the C5 Position, Their Reactions with Nucleophiles and Electrophiles, and Their Polymerase-Catalyzed Incorporation into DNA
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DOI: 10.1021/acsomega.8b00584
Abstract: Transition-metal-catalyzed chlorosulfonylation of 5-ethynylpyrimidine nucleosides provided (E)-5-(β-chlorovinyl)sulfones A, which undergo nucleophilic substitution with amines or thiols affording B. The treatment of vinyl sulfones A with ammonia followed by acid-catalyzed hydrolysis of the intermediary β-sulfonylvinylamines gave… read more here.
Keywords: nucleosides reactive; dna; sulfone; pyrimidine nucleosides ... See more keywords
A Metabolic Engineering Approach to Incorporate Modified Pyrimidine Nucleosides into Cellular RNA.
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DOI: 10.1021/jacs.8b11449
Abstract: The incorporation of modified nucleotides into RNA is a powerful strategy to probe RNA structure and function. While a wide variety of modified nucleotides can be incorporated into RNA in vitro using chemical or enzymatic… read more here.
Keywords: cellular rna; metabolic engineering; rna; pyrimidine nucleosides ... See more keywords