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

Abstract 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 groups. 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 H 2 O without condensing agents to form a new peptide bond.