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Volume 4, Issue 3, 1998, pp. 191-197

Synthesis of peptidomimetics using a polymer-bound Boc-linker

Thomas Redemann, Holger Bandel, GŁnther Jung

Abstract
Boc-resin-bound a-hydroxy-b-amino-aldehydes are accessible starting from N-terminally bound amino acid esters by using Dondoni's C_1-homologation reaction sequence. The conversion of these synthons to two different peptide mimetics - 2-hydroxy-1,3-ethyl-diamines and g-hydroxy-d-amino-vinyl sulfones - has been investigated. The successful transfer of the complex a-amino acid homologation reaction sequence into solid-phase chemistry demonstrates the potentials of the Boc-resin for synthesis of peptidomimetics.

Keywords
a-hydroxy-b-amino-aldehyde, amino acid homologation, Boc-resin, 2-hydroxy-1,3-diamines , g-hydroxy-vinylsulfone, peptidomimetics

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