Fmoc solid-phase synthesis of peptide thioesters by masking as trithioortho esters.
[reaction: see text] Total chemical synthesis of proteins by chemoselective ligation relies on C-terminal peptide thioesters as building blocks. Their preparation by standard Fmoc solid-phase peptide synthesis is made difficult by the lability of thioesters to aminolysis by the secondary amines used for removal of the Fmoc group. Here we present a novel backbone amide linker (BAL) strategy for their synthesis in which the thioester functionality is masked as a trithioortho ester throughout the synthesis.
Brask
Jesper
J
Department of Chemistry, Royal Veterinary and Agricultural University, DK-1871 Frederiksberg, Denmark.
Albericio
Fernando
F
Jensen
Knud J
KJ