Derivatization of Amino Acids and Peptides via Photoredox-Mediated Conjugate Addition
Olivia Zhang, Jeffrey W. Schubert
Abstract
Unnatural amino acids are key building blocks in therapeutically relevant peptides. Thus, the development of novel methods to increase the structural diversity of the unnatural amino acid pool is needed. Herein, a photoredox-mediated decarboxylative radical conjugate addition to dehydroalanine derivatives is disclosed. Mild, robust, and general conditions were identified and applied to the diastereoselective synthesis of unnatural amino acids and the late-stage derivatization of a tripeptide.
Topics & Concepts
ChemistryDehydroalanineConjugateTripeptideDerivatizationAmino acidCombinatorial chemistryPeptideStereochemistryOrganic chemistryBiochemistryHigh-performance liquid chromatographyMathematical analysisMathematicsRadical Photochemical ReactionsChemical Synthesis and AnalysisSulfur-Based Synthesis Techniques