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Author Spotlight: In Silico Creation and Impact of Carbonylated Amino Acids on Protein Structure and Function
Published on: April 26, 2024
Enhancing Reactivity and Site-Selectivity in Hydrogen Atom Transfer from Amino Acid C-H Bonds via Deprotonation
Luca Maria Pipitone1, Giulia Carboni1, Daniela Sorrentino1
1Dipartimento di Scienze e Tecnologie Chimiche, Università "Tor Vergata" , Via della Ricerca Scientifica, 1 I-00133 Rome, Italy.
Abstract:
A kinetic study on the reactions of the cumyloxyl radical (CumO•) with N-Boc-protected amino acids in the presence of the strong organic base DBU has been carried out. CO2H deprotonation increases the electron density at the α-C-H bonds activating these bonds toward HAT to the electrophilic CumO• strongly influencing the intramolecular selectivity. The implications of these results are discussed in the framework of HAT-based aliphatic C-H bond functionalization of amino acids and peptides.
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