Synthesis of Some New Cytidine and Inosine Derivatives.

Abstract

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Synthesis and investigation of the 5-formylcytidine modified, anticodon stem and loop of the human mitochondrial tRNAMet

“…Purification by silica gel chromatography using CHCl 3 : MeOH (80 : 20) with 2% TEA, afforded 966 mg of 2 as a white foam (83% yield). The analytical data obtained matched known literature data for 2 (13).

Figure 2.Synthesis of the 5-formylcytidine phosphoramidite.

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“…A 5-formylcytidine (f 5 C) has previously been synthesized from 5-(hydroxymethyl)cytosine ( 13 ) and from 5-methyluridine ( 30 ), but not incorporated into an RNA sequence. First, we developed a short (four steps) and facile synthesis of f 5 C (compound 5 , Figure 2 ) from commercially available cytidine ( 1 , Figure 2 ), starting by protecting cytidine as the acetonide 2 under standard acid catalysis with an 83% yield.…”

Highly Efficient Method for C-5 Halogenation of Pyrimidine-Based Nucleosides in Ionic Liquids

“…Chlorination of Uridines and Cytidines with N-Chlorosuc-Ms] to give the corresponding brominated derivatives 3a29 and 3b 29 (Table 2, entries 1-8). The reaction time for bromination of 5a and 5b was 30 minutes at 25°C in ILs [MoeMIm][Ms], [BMIm][TFA], and [MoeMIm][TFA], while it took only 20 minutes at 60°C in IL [BMIm][Ms] to give the brominated derivatives 7a22 and 7b36 (Table 2, entries 9-16). These are the shortest reaction times ever reported for nucleoside reactions studied here, and also giving high yields without using any catalyst or oxidizing agent.…”