H. Boyd, I. Calder, S. Leach
Jan 12, 2009
Citations
0
Influential Citations
15
Citations
Journal
International journal of peptide and protein research
Abstract
N-Acylsuccinimides have been examined as potential acylating agents. Three different methods used to synthesize a number of these reagents are described. The rates of hydrolysis of N-acetyl, N-propionyl, N-n-butyryl, N-i-butyryl and N-n-valeryl succinimides and the rates at which they react with n-butylamine in aqueous solution are reported. These N-acylsuccinimides are soluble in water, relatively slow to hydrolyse and yet sufficiently reactive to acylate amines in aqueous solution, even in weak acid solutions. The hydrolysis of N-acetylsuccinimide follows two pathways, giving, as primary products, either N-acetylsuccinamic acid or acetic acid and succinimide. The relative amounts of these hydrolysis products, which were determined by NMR spectroscopy, varies with the pH of hydrolysis.