Solid-phase Synthesis of C-Terminal Peptide Amino Alcohols

The solid-phase syntheses of enkephalin and somatostatin analogues with C-terminal OH functions instead of the normal carboxylates are described. The OH function of the N-terminal amino alcohol was acylated with succinic acid and esterified to the solid support. Normal Boc-TFA solid-phase strategy can be applied to build up and cleave these peptides. The succinic ‘handle’ can be removed by mild basic hydrolysis after cleavage.