Evaluation of the kinetics of hydrolysis of diamino analogues of 2 '- or 3'-deoxyadenosine and of 9-(2-deoxy-beta-D-threo-pentofuranosyl)adenine or 9-(3-deoxy-beta-D-threo-pentofuranosyl)adenine by liquid chromatography
G. Thoithi et al., Evaluation of the kinetics of hydrolysis of diamino analogues of 2 '- or 3'-deoxyadenosine and of 9-(2-deoxy-beta-D-threo-pentofuranosyl)adenine or 9-(3-deoxy-beta-D-threo-pentofuranosyl)adenine by liquid chromatography, NUCLEOS NUC, 18(8), 1999, pp. 1863-1877
The degradation bf diamino analogues of 2'- or :3'-deoxyadenosine and of 9-
(2-deoxy-beta-D-threo-pentofuranosyl)adenine or 9-(3-deoxy-beta-D-threo-pen
tofuranosyl)adenine in buffers of acid, neutral and alkaline pH and constan
t ionic strength was followed by liquid chromatography. The rate of hydroly
sis at acid pH was found to be related to the position and configuration of
the amino group on the sugar moiety. The compounds tinder study were found
to be more stable than corresponding monoaminated nucleosides, which have
been reported to be more stable: than the hydroxyl nucleosides. Liquid chro
matographic analyses indicate that acid hydrolysis involves cleavage of the
N-glycosyl bond as the major degradative process, together with another mi
nor process, pH-rate profiles, activation parameters and deuterium isotope
solvent effects are discussed.