Investigation of the kinetics of degradation of hexopyranosylated cytosine nucleosides using liquid chromatography.
Liquid chromatography was used to follow the degradation of hexopyranosylated cytosine nucleosides in buffers of acid, neutral and alkaline pH and of constant ionic strength. The compounds were found to degrade by hydrolysis to cytosine and/or by deamination to the corresponding uracil nucleosides. Degradation in acid is influenced by the number of sugar hydroxyl groups, presence of sugar double bonds and the type of anomer. Stability of some of the compounds was compared with that of related thymine nucleosides. Temperature studies support a unimolecular mechanism of hydrolysis at pH 1.22.
Thoithi
G N
GN
Katholieke Universiteit Leuven, Laboratorium voor Farmaceutische Chemie en Analyse, Faculteit Farmaceutische Wetenschappen, Belgium.
Van Schepdael
A
A
Busson
R
R
Janssen
G
G
Van Aerschot
A
A
Herdewijn
P
P
Roets
E
E
Hoogmartens
J
J
D002021:Buffers; D002853:Chromatography, Liquid; D003596:Cytosine / Q000031:analogs & derivatives / Q000737:chemistry*; D003641:Deamination; D006358:Hot Temperature; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis; D009705:Nucleosides / Q000737:chemistry*; D009994:Osmolar Concentration
D002021:Buffers; D009705:Nucleosides; D003596:Cytosine