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Biocompatible Macrocyclization between Cysteine and 2-Cyanopyridine Generates Stable Peptide Inhibitors

Nitsche, Christoph; Onagi, Hideki; Quek, Jun-Ping; Otting, Gottfried; Luo, Dahai; Huber, Thomas


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 orthogonal to all proteinogenic amino acids, including cysteine residues that are not at the N-terminus. A substrate peptide of the Zika virus NS2B-NS3 protease cyclized in this way produced an inhibitor...[Show more]

CollectionsANU Research Publications
Date published: 2019-06-12
Type: Journal article
Source: Organic Letters
DOI: 10.1021/acs.orglett.9b01545
Access Rights: Open Access


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