@article{mckinney_warner_young_gage_proulx_2025, title={Oxidative Couplings of <i>N</i>-Aryl Peptides in Organic Solvent: Preventing Amino Acid Side Chain Loss}, volume={6}, DOI={10.1021/acs.orglett.5c01986}, abstractNote={We report conditions for the oxidative coupling of <i>N</i>-aryl peptides with α-nucleophiles in organic solvents, increasing side chain diversity at the site of ligation. While some <i>N</i>-(<i>p</i>-Me<sub>2</sub>N-Ph)-amino acids were found to be unstable in buffer (e.g., Ser, Trp, and Tyr), stable ketoxime linkages were obtained when <i>N</i>-(<i>p</i>-MeO-Ph)-peptides were heated in organic solvents. Such divergent reactivity provides interesting mechanistic insight into oxidative couplings of <i>N</i>-aryl peptides and significantly expands the scope of accessible amino acids at the site of oxime ligation.}, journal={Organic Letters}, author={McKinney, Karlee C. and Warner, Ellen J. T. and Young, Hailey A. and Gage, Sheba C. and Proulx, Caroline}, year={2025}, month={Jun} }