ArticleNucleosides, nucleotides & nucleic acids2015
Practical synthesis of cytidine-5-carboxamide-modified nucleotide reagents.
Article in Nucleosides, nucleotides & nucleic acids, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Combinatorial and rational synthesis of complex, base-modified aptamer libraries on microarrays.RSC advances · 2026Article
- Broadly neutralizing aptamers to SARS-CoV-2: A diverse panel of modified DNA antiviral agents.Molecular therapy. Nucleic acids · 2023Article
- Discovery, Synthesis, and Scale-up of Efficient Palladium Catalysts Useful for the Modification of Nucleosides and Heteroarenes.Molecules (Basel, Switzerland) · 2020Review
- Selection of DNA aptamers with two modified bases.Proceedings of the National Academy of Sciences of the United States of America · 2017Article
- The Toolbox for Modified Aptamers.Molecular biotechnology · 2016Review
- Modified Nucleoside Triphosphates for In-vitro Selection Techniques.Frontiers in chemistry · 2016Review
Corrections and comments
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Authors and funding
6 authors.
Funding
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Abstract
Chemically-modified derivatives of cytidine, bearing a 5-(N-substituted-carboxamide) functional group, are new reagents for use in aptamer discovery via the SELEX process (Systematic Evolution of Ligands by EXponential enrichment). Herein, we disclose a practical synthesis of 5-(N-benzylcarboxamide)-2'-deoxycytidine, and the corresponding 5-(N-1-naphthylmethylcarboxamide)- and 5-(N-3-phenylpropylcarboxamide)-2'-deoxycytidine analogs, as both the suitably-protected 3'-O-cyanoethylphosphoramidite reagents (CEP; gram scale) and the 5'-O-triphosphate reagents (TPP; milligram-scale). The key step in the syntheses is a mild, palladium(0)-catalyzed carboxyamidation of an unprotected 5-iodo-cytidine. Use of the CEP reagents for solid-phase oligonucleotide synthesis was demonstrated and incorporation of the TPP reagents by KOD polymerase in a primer extension assay confirmed the utility of these reagents for SELEX. Finally, the carboxyamidation reaction was also used to prepare the nuclease-resistant sugar-variants: 5-(N-benzylcarboxamide)-2'-O-methyl-cytidine and 5-(N-3-phenylpropylcarboxamide)-2'-deoxy-2'-fluoro-cytidine.
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