Evaluation of the kinetics of hydrolysis of monoamino analogues of 2'- or 3'-deoxyadenosine and of 9-(2-deoxy¬b-d-threo-pentofuranosyl)adenine or 9-(3-deoxy¬b-d-threo-pentofuranosyl)adenine by liquid chromatography

Abstract

Liquid chromatography was used to follow the degradation of monoamino analogues of 2'- or 3'¬deoxyadenosine and of 9-(2-deoxy-B-D-threo-pentofurano¬syl) adenine or 9-(3-deoxy-B-D-threo-pentofuranosyl) adeni nein buffers of different pH and constant ionic strength (f..L). Comparison of stabilities of some of the compounds under study with those of corresponding hydroxyl analogues showed that at acid pH the aminated compounds are more stable than the corresponding hydroxyl compounds. The higher stability associated with the presence of an amino group in the sugar is explained in function of pKa values, which were determined by l3c NMR.