The use of N^ε-2-Hydroxyarylmethylene-protected ornithine and lysine derivatives in solid-phase peptide synthesis

Abstract

N^α-t-Butoxycarbonyl-N^ε-(2-hydroxyarylmethylene)-ornithine and -lysine have been synthesized and coupled with amino acyl resins in the presence of dicyclohexylcarbodiimide to form N-protected peptide resin esters. The ketimine protecting group was found to be stable under anhydrous conditions and the urethane blocking group could be removed preferentially. A number of lysine- and ornithine- containing peptides have been synthesized by the solid-phase technique.