Study of the influence of derivatization conditions on the structure and stability of nucleoside derivatives using gas chromatography-mass spectrometry

Conditions of the derivatization of nucleosides are studied using various reagents. Single trimethylsilyl derivatives of uridine, 5-methyluridine, cytidine, 5-methylcytidine, inosine, xanthosine, N 2,N 2-dimethylguanosine were obtained by reaction with N,O-bis(trimethylsilyl)trifluoroacetamide. A mixture of trimethylsilyl derivatives of adenosine and guanosine formed under these conditions. N-trifluoroacetyl-O-trimethylsilyl derivatives of cytidine, 5-methylcytidine, adenosine (in mixture with trimethylsilyl derivative) were prepared using N,O-bis(trimethylsilyl)trifluoroacetamide and N-methyl-bis(trifluoroacetamide) (mixed derivatization). Derivatives of cytidine and 5-methylcytidine obtained by mixed derivatization possessed better chromatographic characteristics compared to trimethylsilyl derivatives. The formation of a trifluoroacetyl derivatives of adenosine by the action of N-methyl-bis(trifluoroacetamide) is shown. The possibility of the replacement of the reagent and pyridine by an inert solvent is studied.