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Updated: Aug 17, 2026

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
Published on: April 27, 2017
Hydrolysis of the prodrug, 2',3',5'-triacetyl-6-azauridine
C M Riley1, M A Mummert, J Zhou
1Department of Pharmaceutical Chemistry, University of Kansas, Lawrence 66045-2504, USA.
Purpose:
The purposes were to study the kinetics of hydrolysis of 2',3',5'-triacetyl-6-azauridine (1) in aqueous solution (mu = 0.5) and to identify the main intermediates and products of the reaction.
Methods:
A stability indicating isocratic LC assay was used to study the rate of degradation of 1. A gradient LC assay was used to study the time courses of the degradants. The products of hydrolysis were isolated by preparative liquid chromatography and identified by 1H-NMR and CI-MS. The pKa value was obtained by potentiometric titration.
Results:
At 36.8 degrees C, the pH-rate profile of 1 in water was adequately described by a four-term rate equation. The intermediates were identified as the primary and secondary di-acetates, and the primary and secondary mono-acetates. The final product was 6-azauridine.
Conclusions:
A simplified kinetic scheme could be used to describe the concentration-time profiles of 1, the intermediates and the final product.
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