Post-Assembly Modification of Head-to-Tail Cyclic Peptides by Methionine-Directed β-C(sp<sup>3</sup>)–H Arylation
Gang Li, Feipeng Yuan, Bo Yao
Abstract
Peptide modification by C(sp3)–H functionalization of internal residues remains a major challenge due to the inhibitory effect of peptide bonds. In this work, we developed a methionine-directed β-C(sp3)–H arylation method for internal alanine functionalization. By tuning the σC–C bond rotation of internal Ala through head-to-tail cyclization, we overcame the inhibitory effect and functionalized a wide range of head-to-tail cyclic peptides with aryl iodides with excellent position selectivity.
Topics & Concepts
ChemistrySurface modificationPeptideMethionineAlanineStereochemistryArylCyclic peptideSelectivityHead (geology)Combinatorial chemistryAmino acidOrganic chemistryBiochemistryCatalysisAlkylGeologyPhysical chemistryGeomorphologyCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsFluorine in Organic Chemistry