<i>N</i>‐Terminal Selective C−H Azidation of Proline‐Containing Peptides: a Platform for Late‐Stage Diversification
Emmanuelle M. D. Allouche, Raphaël Simonet‐Davin, Jérôme Waser
Abstract
A methodology for the C-H azidation of N-terminal proline-containing peptides was developed employing only commercially available reagents. Peptides bearing a broad range of functionalities and containing up to 6 amino acids were selectively azidated at the carbamate-protected N-terminal residue in presence of the numerous other functional groups present on the molecules. Post-functionalizations of the obtained aminal compounds were achieved: cycloaddition reactions or C-C bond formations via a sequence of imine formation/nucleophilic addition were performed, offering an easy access to diversified peptides.
Topics & Concepts
ChemistryResidue (chemistry)CarbamateImineProlineStereochemistryCycloadditionAminalCombinatorial chemistryReagentNucleophileTotal synthesisAmino acidOrganic chemistryBiochemistryCatalysisSynthesis and Catalytic ReactionsChemical Synthesis and AnalysisOxidative Organic Chemistry Reactions