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Published on: November 22, 2024
Oxidative Couplings of N-Aryl Peptides in Organic Solvent: Preventing Amino Acid Side Chain Loss
Karlee C McKinney1, Ellen J T Warner1, Hailey A Young1
1Department of Chemistry, North Carolina State University, Raleigh, North Carolina 27695-8204, United States.
Abstract:
We report conditions for the oxidative coupling of N-aryl peptides with α-nucleophiles in organic solvents, increasing side chain diversity at the site of ligation. While some N-(p-Me2N-Ph)-amino acids were found to be unstable in buffer (e.g., Ser, Trp, and Tyr), stable ketoxime linkages were obtained when N-(p-MeO-Ph)-peptides were heated in organic solvents. Such divergent reactivity provides interesting mechanistic insight into oxidative couplings of N-aryl peptides and significantly expands the scope of accessible amino acids at the site of oxime ligation.
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