Influence of a remote oh group on the stability of the phosphoramide bond in an ester of uridylyl(5′→N)alanine
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1. The ethyl and hydroxyethyl esters of uridylyl(5′→N) alanine have been synthesized and their comparative hydrolytic stabilities in the pH region from 0 to 8 have been studied.
2. It has been shown that the presence of a remote hydroxy group in the molecule of a uridylyl(5′→N)amino acid makes the phosphoramide link more labile in the region of weakly acid and neutral pH values.
3. At pH 3–5, the hydroxy ethyl ester of uridylyl(5′→N)alanine undergoes an intramolecular rearrangement with the cleavage of the phosphoramide linkage and the formation of a phosphoric diester linkage.
KeywordsHydroxyl Oxygen Phosphoramide Azeotropic Distillation Caustic Potash Dihydropyran
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