Stability studies of hydrazide and hydroxylamine-based glycoconjugates in aqueous solution
| Autor: | Anna V. Gudmundsdottir, Mark Nitz, Caroline E. Paul |
|---|---|
| Rok vydání: | 2009 |
| Předmět: |
Glycoconjugate
Hydroxylamines Hydrazide Biochemistry Analytical Chemistry chemistry.chemical_compound Hydrolysis Hydroxylamine Drug Stability Nucleophile Monosaccharide Organic chemistry chemistry.chemical_classification Aqueous solution Molecular Structure Organic Chemistry Water General Medicine Hydrogen-Ion Concentration Solutions Hydrazines Carbohydrate Sequence chemistry Glycoconjugates Conjugate |
| Zdroj: | Carbohydrate Research. 344:278-284 |
| ISSN: | 0008-6215 |
| DOI: | 10.1016/j.carres.2008.11.007 |
| Popis: | Glycoconjugates can be readily formed by the condensation of a free-reducing terminus and a strong alpha-effect nucleophile, such as a hydrazide or a hydroxylamine. Further characterization of a series of glycoconjugates formed from xylose, glucose and N-acetylglucosamine, and either p-toluenesulfonyl hydrazide or an N-methylhydroxylamine, was carried out to gain insight into the optimal conditions for the formation of these useful conjugates, and their stability. Their apparent association constants (9-74 M(-1)) at pH 4.5; as well, as rate constants for hydrolysis, at pH 4.0, 5.0 and 6.0 (37 degrees C), were determined. The half-lives of the conjugates varied between 3h and 300 days. All the compounds were increasingly stable as the pH approached neutrality. Conjugate hydrolysis rates mirrored those found for O-glycoside hydrolysis where conjugates formed from electron-rich monosaccharides hydrolyzed more rapidly. |
| Databáze: | OpenAIRE |
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