A new method for the solid phase synthesis of hydroxyethylamine peptide bond isosteres: Synthesis of an HIV-1 protease inhibitor and of a β-casomorphin-5 analogue

Article abstract of DOI:10.1016/S0040-4039(00)73945-1

A solid phase synthesis procedure for the preparation of hydroxyethylamine peptide isosteres is described. Reductive amination of the resin-bound peptide with an α-hydroxyaldehyde, prepared via 2-(trimethylsilyl)thiazole addition to Boc-phenylalaninal or Boc-prolinal, produces the peptides in good yield.