Synthesis of peptidomimetics using a polymer-bound Boc-linker

Abstract

Boc-resin-bound α-hydroxy-β-amino-aldehydes are accessible starting from N-terminally bound amino acidesters by using Dondoni's C^sub 1^-homologationreaction sequence. The conversion of these synthons totwo different peptide mimetics - 2-hydroxy-1,3-ethyl-diamines and γ-hydroxy-δ-amino-vinyl sulfones - hasbeen investigated. The successful transfer of thecomplex α-amino acid homologation reactionsequence into solid-phase chemistry demonstrates thepotentials of the Boc-resin for synthesis of peptidomimetics.[PUBLICATION ABSTRACT]