Modifications of nucleosides and nucleotides

Add time:07/29/2019    Source:sciencedirect.com

1. Girard-P reagent (acetohydrazide pyridinium chloride) has been found to replace the C-4 amino group of N1-substituted cytosine and cytidylic acids with an acetohydrazidopyridinium residue. The reaction took place at a maximum rate at pH 4.2 and followed a pseudo first-order rate.2. The reaction was found to be absolutely specific for cytosine nucleotides and no reaction between Girard-P reagent and adenylic, guanylic or uridylic acid was observed in the pH range 4.0–7.0 and 37°.3. The position of substitution of the acetohydrazidopyridinium group in the cytosine moiety was confirmed by identification of the product of the reaction between Girard-P reagent and N1-methylcytosine with N1-methyl-4-deamino-4-acetohydrazidopyridinium cytosine which was obtained by the reaction of N1-methyl-4-thiouracil with Girard-P reagent.4. 4-Deamino-4-acetohydrazidopyridinium cytidine 2′,3′-cyclic phosphate was remarkably resistant to hydrolysis by bovine pancreatic ribonuclease (ribonucleate pyrimidine-nucleotido-2′-transferase (cyclizing), EC 2.7.7.16).

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