Alkenyl Building Blocks for Stapled Peptides
Stapled peptides are formed by incorporating special amino acids with olefinic side chains at the i and i+4 positions (one-loop staple) or at i and i+7 positions (two-loop staple). The hydrocarbon bridge is formed by a ring-closing metathesis reaction catalyzed by benzylidenebis(tricyclohexyl-phosphine)-dichlororuthenium (Grubb’s catalyst).
Stapled peptides are good drug leads due to these features:
• Retain active conformation
• Permeate cell membranes
• Resist proteolysis for longer duration
Stapled Peptide Literature
Molola, M; Memeo, MG; Quadrelli, P. Molecules, 2019, 24(20), 3654.
Achek, A; Shah, M; Seo, JY; et al. J. Med. Chem., 2019, 62(14), 6495-6511.
Maisel, SA; Broka, D; Atwell, B; et al. J. Transl. Med., 2019, 17(1), 201.
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