Biocompatible macrocyclization between cysteine and 2-cyanopyridine generates stable peptide inhibitors

• Main Authors: Nitsche, Christoph, Onagi, Hideki, Quek, Jun-Ping, Otting, Gottfried, Luo, Dahai, Huber, Thomas
• Other Authors: Lee Kong Chian School of Medicine (LKCMedicine)
• Format: Article
• Language: English
• Published: 2020
• Subjects: Science::Medicine; Peptides and Proteins; Monomers
• Online Access: https://hdl.handle.net/10356/140796
• Institution: Nanyang Technological University

Peptides featuring an N-terminal cysteine residue and the unnatural amino acid 3-(2-cyano-4-pyridyl)alanine (Cpa) cyclize spontaneously in aqueous solution at neutral pH. Cpa is readily available and easily introduced into peptides using standard solid-phase peptide synthesis. The reaction is orthog...