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Asparaginyl Endopeptidase-Mediated Peptide Cyclization for Phage Display

Xiao-Cui Wan, Yanni Zhang, Hua Zhang, Ying Chen, Zhihui Cui, Wenjing Zhu, Ge‐Min Fang

2024Organic Letters13 citationsDOI

Abstract

We report here an enzymatic strategy for asparaginyl endopeptidase-mediated peptide cyclization. Incorporation of chloroacetyl groups into the recognition sequence of Oa AEP1 enabled intramolecular cyclization with Cys residues. Combining this strategy and phage display, we identified nanomolar macrocyclic peptide ligands targeting TEAD4. One of the bicyclic peptides binds to TEAD4 with a K D value of 139 nM, 16 times lower than its linear analogue, demonstrating the utility of this platform in discovering high-affinity macrocyclic peptide ligands.

Topics & Concepts

PeptideChemistryPhage displayEndopeptidaseCyclic peptideStereochemistryOligopeptideCombinatorial chemistryEnzymeNeprilysinIntramolecular forcePeptide libraryBiochemistryPeptide sequenceGeneBiochemical and Structural CharacterizationChemical Synthesis and AnalysisGlycosylation and Glycoproteins Research