Synthesis of peptidomimetics using a polymer-bound Boc-linker
Thomas Redemann, Holger Bandel, Günther 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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