Facile hydrolysis and formation of amide bonds by N-hydroxyethylation of α-amino acids

Article abstract of DOI:10.1016/S0040-4039(97)00330-4

The C-terminal amides of α-amino acids are readily hydrolyzed at 25°and pH 7 when the N-terminus is N-hydroxyethylated, with one or two hydroxyethyl The reaction proceeds via cyclization to a morpholinolactone (2) which is rapidly hydrolyzed by water. In the presence of equimolar amounts of amines or amino acid derivatives, 2 reacts in H₂O without condensing agents to form a new peptide bond.