Polymer-Bound Oxime Esters as Supports for Solid-Phase Peptide Synthesis. Preparation of Protected Peptide Fragments.

Article abstract of DOI:10.1021/jo01295a026

A series of polystyrene-bound substituted benzophenone oximes (II) have been synthesized and tested as potential supports for the solid-phase preparation of protected peptide fragments.The polymer-bound p-nitrobenzophenone oxime (IID) has been found to be a suitable support for stepwise peptide synthesis.Protected peptides can be assembled on IID by coupling and deprotection steps similar to those employed in the usual Merrifield solid-phase procedures.Cleavage of peptides from IID can be accomplished with hydrazine and amino acid esters under mild conditionswhich do not affect benzyl ester side-chain protecting groups.The utility of IID has been illustrated in the synthesis of protected peptide hydrazides and esters, several of which have aspartic and glutamic acid side chains protected by benzyl groups.