Allouche, Emmanuelle M. D.Simonet-Davin, RaphaelWaser, Jerome2022-03-142022-03-142022-03-142022-02-2310.1002/chem.202200368https://infoscience.epfl.ch/handle/20.500.14299/186252WOS:000761467800001A 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.Chemistry, MultidisciplinaryChemistryamino acidsazidationc-h functionalizationpeptidesselectivityhypervalent iodine oxidationmetal-catalyzed azidationprotein therapeuticstrimethylsilyl azidefunctionalizationderivativeschemistrysystemazidonationstrategiestext::journal::journal article::research article