Related Experiment Video
Updated: Oct 4, 2026
On-line Analysis of Nitrogen Containing Compounds in Complex Hydrocarbon Matrixes
Published on: August 5, 2016
Direct measurement of pyrimidine C6-hydrate stability
K Nolan Carter1, M M Greenberg
1Department of Chemistry, Colorado State University, Fort Collins, CO 80523, USA.
Abstract:
Pyrimidine C6-hydrates are produced via UV-irradiation and undergo dehydration upon standing. The stability of these compounds has a direct bearing on their genotoxicity. The rate constants for elimination from 5'-benzyoylated derivatives of 5,6-dihydro-5-hydroxythymidine (6) and 5,6-dihydro-5-hydroxy-2'-deoxyuridine (9) were measured directly via HPLC. The rate constants for dehydration increase from pH 6.0 to 8.0. The half-lives for 6 and 9 at pH 7.4 and 37 degrees C are 46.5 and 24.4h, respectively. Deglycosylation is not observed, even upon heating at 90 degrees C. These observations reinforce proposals that pyrimidine hydrates are sufficiently long-lived that they can exert significant effects on biological systems.
Related Concept Videos
01:15¹H NMR of Conformationally Flexible Molecules: Variable-Temperature NMR
02:30Stability of Substituted Cyclohexanes
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...