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Creators/Authors contains: "Tsai, Hsu‐Chun"

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  1. ; ; ; ; ; ; ; ; ; (, ChemBioChem)
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  2. ; ; (, Current Protocols in Nucleic Acid Chemistry)
    Abstract This article contains detailed synthetic protocols for preparation of 5‐cyanomethyluridine (cnm5U) and 5‐cyanouridine (cn5U) phosphoramidites. The synthesis of the cnm5U phosphoramidite building block starts with commercially available 5‐methyluridine (m5C), followed by bromination of the 5‐methyl group to install the cyano moiety using TMSCN/TBAF. The cn5U phosphoramidite is obtained by regular Vorbrüggen glycosylation of the protected ribofuranose with silylated 5‐cyanouracil. These two modified phosphoramidites are suitable for synthesis of RNA oligonucleotides on solid phase using conventional amidite chemistry. Our protocol provides access to two novel building blocks for constructing RNA‐based therapeutics. © 2020 Wiley Periodicals LLC. Basic Protocol 1: Preparation of cnm5U and cn5U phosphoramidites Basic Protocol 2: Synthesis, purification, and characterization of cnm5U‐ and cn5U‐modified RNA oligonucleotides 
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