Effect of piperidine on benzylaspartyl peptides in solution and in the solid phase

Abstract

Basic conditions (e.g. piperidinolysis), used for the removal of the N^α-9-fluorenylmethyloxycarbonyl group, lead to significant cleavage of side-chain benzyl esters of peptides containing benzylaspartyl residues both in solution and solid-phase syntheses; the intermediate imide derivative is slowly transformed to a mixture of piperidides.