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

• Published in: Journal of analytical chemistry (New York, N.Y.) Vol. 69; no. 14; pp. 1307 - 1312
• Main Authors: Razvazhnaya, O. V., Burmykin, D. A., Revelsky, A. I.
• Format: Journal Article
• Language: English
• Published: Moscow Pleiades Publishing 30.12.2014; Springer
• Subjects: Analytical Chemistry; Chemical properties; Chemical reactions; Chemistry; Chemistry and Materials Science; Gas chromatography; Identification and classification; Mass spectrometry; Methods; Nucleosides; nucleosides; gas chromatography/mass spectrometry; silylation; acylation
• ISSN: 1061-9348; 1608-3199
• DOI: 10.1134/S106193481414007X

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.