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Efficient Synthesis of N-4-Methyl- and N-4-Hydroxycytidine Phosphoramidites

  作者 LU JUN; LI NANSHENG; KOO SELENE C; PICCIRILLI JOSEPH A  
  选自 期刊  Synthesis;  卷期  2010年-16;  页码  2708-2712  
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[摘要]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.

 
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