Synthesis of peptidomimetics using a polymer-bound Boc-linker.
Boc-resin-bound alpha-hydroxy-beta-amino-aldehydes are accessible starting from N-terminally bound amino acid esters by using Dondoni's C1-homologation reaction sequence. The conversion of these synthons to two different peptide mimetics--2-hydroxy-1,3-ethyl-diamines and gamma-hydroxy-delta-amino-vinyl sulfones--has been investigated. The successful transfer of the complex alpha-amino acid homologation reaction sequence into solid-phase chemistry demonstrates the potentials of the Boc-resin for synthesis of peptidomimetics.
Redemann
T
T
Institut für Organische Chemie, Tübingen, Germany.
Bandel
H
H
Jung
G
G
D000596:Amino Acids / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D003959:Diamines / Q000138:chemical synthesis; D008401:Gas Chromatography-Mass Spectrometry; D008956:Models, Chemical; D010455:Peptides / Q000138:chemical synthesis*; D011108:Polymers / Q000737:chemistry; D012116:Resins, Plant / Q000737:chemistry
D000596:Amino Acids; D003959:Diamines; D010455:Peptides; D011108:Polymers; D012116:Resins, Plant