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Cyclobutane-bearing restricted anchoring residues enabled geometry-specific hydrocarbon peptide stapling

Baobao Chen, Chao Liu, Wei Cong, Fei Gao, Yan Zou, Li Su, Lei Liu, Alexander Hillisch, Lutz Lehmann, Donald Bierer, Xiang Li, Honggang Hu

2023Chemical Science15 citationsDOIOpen Access PDF

Abstract

geometry-specific stapled peptides indeed exhibit higher α-helicity and thus stronger biological activity than canonical hydrocarbon stapled peptides. We believe that this methodology possesses great potential to expand the scope of the existing peptide stapling strategy. These cyclobutane-bearing restricted anchoring residues served as effective supplements for the existing olefin-terminated unnatural amino acids and the resultant geometry-specific hydrocarbon peptide stapling provided more potential for peptide therapeutics.

Topics & Concepts

CyclobutaneChemistryPeptideAmino acidStereochemistryRational designCyclobutanesCombinatorial chemistryRing (chemistry)BiochemistryOrganic chemistryNanotechnologyMaterials scienceChemical Synthesis and AnalysisClick Chemistry and ApplicationsAntimicrobial Peptides and Activities
Cyclobutane-bearing restricted anchoring residues enabled geometry-specific hydrocarbon peptide stapling | Litcius