利用液相色谱法研究己糖基化胞嘧啶核苷的降解动力学

Investigation of the kinetics of degradation of hexopyranosylated cytosine nucleosides using liquid chromatography.

作者信息

Thoithi G N, Van Schepdael A, Busson R, Janssen G, Van Aerschot A, Herdewijn P, Roets E, Hoogmartens J

机构信息

Katholieke Universiteit Leuven, Laboratorium voor Farmaceutische Chemie en Analyse, Faculteit Farmaceutische Wetenschappen, Belgium.

出版信息

Nucleosides Nucleotides Nucleic Acids. 2000 Jan-Feb;19(1-2):189-203. doi: 10.1080/15257770008033003.

DOI:10.1080/15257770008033003

PMID:10772709

Abstract

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.

摘要

采用液相色谱法跟踪己吡喃糖基化胞嘧啶核苷在酸性、中性和碱性pH值以及恒定离子强度缓冲液中的降解情况。发现这些化合物通过水解降解为胞嘧啶和/或通过脱氨作用降解为相应的尿嘧啶核苷。酸性条件下的降解受糖羟基数量、糖双键的存在以及异头物类型的影响。将其中一些化合物的稳定性与相关胸腺嘧啶核苷的稳定性进行了比较。温度研究支持在pH 1.22时的单分子水解机制。