Jun Lu, Nan-Sheng Li, Selene C. Koo
Aug 1, 2010
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Journal
Synthesis
Abstract
Nucleotide analogues empower chemical biologists to investigate the relationship between RNA structure and function on a level deeper than would be possible using only the four natural nucleotides. N 4 -Methylcytidine and N 4 -hydroxycytidine represent two cytidine analogues whose physicochemical properties enable biochemical tests for specific aspects of cytidine function within RNA. Here, we describe an efficient synthesis of N 4 -methylcytidine and N 4 -hydroxycytidine derivatives, and their corresponding phosphoramidites in 40.7% and 25.2% yield, respectively, starting from uridine. These phosphoramidites couple efficiently during solid-phase synthesis, although N 4 -hydroxycytidine reverts partially to cytidine (5-10%) during oligonucleotide synthesis and deprotection.