Differential scanning calorimetry—thin layer chromatography study of ribonucleosides

Thermal mutagenesis has been associated with cleavage of the glycosidic bond and modification of the base structure. Using deoxynucleosides as models, thermal analysis has been utilized to determine the influence of structure on relative ease of these thermolysis reactions. Differential enthalpic analyses of series of crystalline ribonucleosides indicate that they are more resistent to glycosidic cleavage than are the corresponding 2′—deoxyribonucleosides. This difference in thermal stability is attributed to the retarding influence of the 2′-hydroxyl group on the initiation of ion pair formation in the proposed cyclic transition state. Cytosine exhibits a unique behavior insofar as partial deamination of the base occurs, subsequent to cleavage from the sugar, to yield uracil as indicated by a combined DSC-TLC analysis.