Title: 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
Authors: Thoithi, G ×
Van Schepdael, Ann
Vinckier, Christiaan
Herdewijn, Piet
Roets, Eugene
Hoogmartens, Jos #
Issue Date: Jan-1999
Publisher: Marcel dekker inc
Series Title: Nucleosides & nucleotides vol:18 issue:8 pages:1863-1877
Abstract: 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-pentofuranosyl)adenine in buffers of acid, neutral and alkaline pH and constant ionic strength was followed by liquid chromatography. The rate of hydrolysis 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 chromatographic analyses indicate that acid hydrolysis involves cleavage of the N-glycosyl bond as the major degradative process, together with another minor process, pH-rate profiles, activation parameters and deuterium isotope solvent effects are discussed.
ISSN: 0732-8311
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Pharmaceutical Analysis
Molecular Design and Synthesis
Medicinal Chemistry (Rega Institute)
× corresponding author
# (joint) last author

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