Synthesis of 5-Cyanomethyluridine (cnm5U) and 5-Cyanouridine (cn5U) Phosphoramidites and Their Incorporation into RNA Oligonucleotides

Mao S.; Tsai H.-C.; Sheng J.

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Synthesis of 5-Cyanomethyluridine (cnm5U) and 5-Cyanouridine (cn5U) Phosphoramidites and Their Incorporation into RNA Oligonucleotides

机译：Synthesis of 5-Cyanomethyluridine (cnm5U) and 5-Cyanouridine (cn5U) Phosphoramidites and Their Incorporation into RNA Oligonucleotides

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© 2020 Wiley Periodicals LLCThis 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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《current protocols in nucleic acid chemistry》 |2020年第1期|共页
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Mao S.; Tsai H.-C.; Sheng J.;
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Department of Chemistry and The RNA Institute University at Albany State University of New York;

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cyano-modification; nucleic acids; phosphoramidite; solid phase synthesis;

Synthesis of 5-Cyanomethyluridine (cnm5U) and 5-Cyanouridine (cn5U) Phosphoramidites and Their Incorporation into RNA Oligonucleotides

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