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Synthesis and Multiple Incorporations of 2′‐ O ‐Methyl‐5‐hydroxymethylcytidine, 5‐Hydroxymethylcytidine and 5‐Formylcytidine Monomers into RNA Oligonucleotides
Author(s) -
Tanpure Arun A.,
Balasubramanian Shankar
Publication year - 2017
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201700492
Subject(s) - phosphoramidite , monomer , oligonucleotide , rna , cytosine , chemistry , function (biology) , 5 methylcytosine , combinatorial chemistry , stereochemistry , biochemistry , biology , organic chemistry , dna , polymer , gene , dna methylation , gene expression , genetics
The synthesis of 2′‐ O ‐methyl‐5‐hydroxymethylcytidine (hm 5 Cm), 5‐hydroxymethylcytidine (hm 5 C) and 5‐formylcytidine (f 5 C) phosphoramidite monomers has been developed. Optimisation of mild post‐synthetic deprotection conditions enabled the synthesis of RNA containing all four naturally occurring cytosine modifications (hm 5 Cm, hm 5 C, f 5 C plus 5‐methylcytosine). Given the considerable interest in RNA modifications and epitranscriptomics, the availability of synthetic monomers and RNAs containing these modifications will be valuable for elucidating their biological function(s).