Synthesis of trifunctional cyclo-β-tripeptide templates

• Frank Stein,
• Tahir Mehmood,
• Tilman Plass,
• Javid H. Zaidi and
• Ulf Diederichsen

Beilstein J. Org. Chem. 2012, 8, 1576–1583, doi:10.3762/bjoc.8.180

• ; cyclic β-tripeptide scaffold; orthogonal protection groups; peptide synthesis; template-assembled synthetic proteins (TASP); Introduction Cyclic β-tripeptides form structurally well-defined secondary structures with the potential for alignment of the rings to form intermolecular aggregates [1]. Due to

• silver benzoate and water as a nucleophile [19][20][21][22][23] yielding the homo-β-lysine derivatives 1 and 2 alongside the azide β-amino acid 3 (Figure 2). In previous studies, synthesis of the cyclic β-tripeptide scaffold was provided by cyclization of the linear β-tripeptide obtained by solution