Synthesis and Purification of N3-Methylcytidine (m3C) Modified RNA Oligonucleotides

Johnsi Mathivanan; Jinxi Du; Song Mao; Ya Ying Zheng; Jia Sheng

doi:10.1002/cpz1.307

Synthesis and Purification of N³-Methylcytidine (m³C) Modified RNA Oligonucleotides

Johnsi Mathivanan
, Jinxi Du
, Song Mao
, Ya Ying Zheng
, Jia Sheng

Chemistry

University at Albany

SUNY Albany

Research output: Contribution to journal › Article › peer-review

4 Scopus citations

Abstract

This protocol describes a step-by-step chemical synthesis approach to prepare N³-methylcytidine (m³C) and its phosphoramidite. The method for synthesizing m³C starts from commercially available cytidine, and proceeds via N³-methylation in the presence of MeI, which generates the N³-methylcytidine (m³C) nucleoside, followed by the installation of several protecting groups at sites that include the 5'-hydroxyl group (4,4'-dimethoxytrityl protection), the 4-amino group (benzoyl protection), and the 2'-hydroxyl group (tert-butyldimethylsilyl, TBDMS, protection). Standard phosphoramidite chemistry is applied to prepare the final m³C phosphoramidite for solid-phase synthesis of a series of RNA oligonucleotides.

Original language	English
Article number	e307
Journal	Current Protocols
Volume	1
Issue number	11
DOIs	https://doi.org/10.1002/cpz1.307
State	Published - Nov 2021

Keywords

N3-methylcytidine
RNA modification
phosphoramidite
solid-phase synthesis

Access to Document

10.1002/cpz1.307

Cite this

@article{41107aa1b0a745c69d1bb750d54f4861,

title = "Synthesis and Purification of N3-Methylcytidine (m3C) Modified RNA Oligonucleotides",

abstract = "This protocol describes a step-by-step chemical synthesis approach to prepare N3-methylcytidine (m3C) and its phosphoramidite. The method for synthesizing m3C starts from commercially available cytidine, and proceeds via N3-methylation in the presence of MeI, which generates the N3-methylcytidine (m3C) nucleoside, followed by the installation of several protecting groups at sites that include the 5'-hydroxyl group (4,4'-dimethoxytrityl protection), the 4-amino group (benzoyl protection), and the 2'-hydroxyl group (tert-butyldimethylsilyl, TBDMS, protection). Standard phosphoramidite chemistry is applied to prepare the final m3C phosphoramidite for solid-phase synthesis of a series of RNA oligonucleotides.",

keywords = "N3-methylcytidine, RNA modification, phosphoramidite, solid-phase synthesis",

author = "Johnsi Mathivanan and Jinxi Du and Song Mao and Zheng, \{Ya Ying\} and Jia Sheng",

note = "Publisher Copyright: {\textcopyright} 2021 Wiley Periodicals LLC",

year = "2021",

month = nov,

doi = "10.1002/cpz1.307",

language = "English",

volume = "1",

journal = "Current Protocols",

issn = "1934-8525",

publisher = "John Wiley and Sons Inc.",

number = "11",

}

TY - JOUR

T1 - Synthesis and Purification of N3-Methylcytidine (m3C) Modified RNA Oligonucleotides

AU - Mathivanan, Johnsi

AU - Du, Jinxi

AU - Mao, Song

AU - Zheng, Ya Ying

AU - Sheng, Jia

PY - 2021/11

Y1 - 2021/11

N2 - This protocol describes a step-by-step chemical synthesis approach to prepare N3-methylcytidine (m3C) and its phosphoramidite. The method for synthesizing m3C starts from commercially available cytidine, and proceeds via N3-methylation in the presence of MeI, which generates the N3-methylcytidine (m3C) nucleoside, followed by the installation of several protecting groups at sites that include the 5'-hydroxyl group (4,4'-dimethoxytrityl protection), the 4-amino group (benzoyl protection), and the 2'-hydroxyl group (tert-butyldimethylsilyl, TBDMS, protection). Standard phosphoramidite chemistry is applied to prepare the final m3C phosphoramidite for solid-phase synthesis of a series of RNA oligonucleotides.

AB - This protocol describes a step-by-step chemical synthesis approach to prepare N3-methylcytidine (m3C) and its phosphoramidite. The method for synthesizing m3C starts from commercially available cytidine, and proceeds via N3-methylation in the presence of MeI, which generates the N3-methylcytidine (m3C) nucleoside, followed by the installation of several protecting groups at sites that include the 5'-hydroxyl group (4,4'-dimethoxytrityl protection), the 4-amino group (benzoyl protection), and the 2'-hydroxyl group (tert-butyldimethylsilyl, TBDMS, protection). Standard phosphoramidite chemistry is applied to prepare the final m3C phosphoramidite for solid-phase synthesis of a series of RNA oligonucleotides.

KW - N3-methylcytidine

KW - RNA modification

KW - phosphoramidite

KW - solid-phase synthesis

UR - https://www.scopus.com/pages/publications/85120341374

U2 - 10.1002/cpz1.307

DO - 10.1002/cpz1.307

M3 - Article

C2 - 34792865

SN - 1934-8525

VL - 1

JO - Current Protocols

JF - Current Protocols

IS - 11

M1 - e307

ER -

Synthesis and Purification of N³-Methylcytidine (m³C) Modified RNA Oligonucleotides

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this