On-resin cyclization of a head-to-tail cyclopeptide using an allyldimethylsilyl polystyrene resin pre-loaded by metathesis

Abstract

Here, we report the solid-phase synthesis of a 17-mer cyclopeptide which is expected to have anti-angiogenic properties. The peptidic synthesis is performed on an allyldimethylsilyl polystyrene support loaded by metathesis with a conveniently functionalized d-Tyrosine amino acid. The linear peptide was assembled by standard Fmoc chemistry and on-resin cyclization was enabled after selective deprotection of the C-terminal group with 2% hydrazine/DMF at room temperature. Final cleavage was realized under mild acidic conditions allowing to obtain a cyclopeptide under partially protected form.