Solid-Phase Photochemical Peptide Homologation Cyclization
Michael Elbaum, Mahmoud A. Elkhalifa, Gary A. Molander, David M. Chenoweth
Abstract
Forging new C(sp3)–C(sp3) bonds to central positions within a peptide backbone is critical for the development of new therapeutics and chemical probes. Currently, there are no methods for decarboxylating Asp and Glu side chains solid-phase photochemically or using such radicals to form peptide macrocycles. Herein, electron-donor-acceptor complexes between Hantzsch ester and on-resin peptide N-hydroxyphthalimide radical precursors are used to access these radicals, demonstrated with two-carbon homologations and homologation cyclizations of Atosiban and RGDf.
Topics & Concepts
ChemistryRadicalPeptidePhotochemistryAcceptorPhase (matter)Combinatorial chemistrySide chainStereochemistryOrganic chemistryBiochemistryCondensed matter physicsPhysicsPolymerChemical Synthesis and AnalysisRadical Photochemical ReactionsFluorine in Organic Chemistry