Bioconjugation Development for Aliphatic Amino Acids

Bedre, Ishani

Student Work

Bioconjugation Development for Aliphatic Amino Acids

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Photoredox mediated hydrogen atom abstraction of Csp3-H bonds has been a growing and underexplored area of C-H Functionalization. The Musacchio group has mapped a mechanism that consists of carbocation intermediate generation via formal hydrogen atom transfer (HAT) and sequential radical polar crossover (RPC) event. This alternative enables circumvention of the energetic barrier present in a direct hydride abstraction. Excitation of a photocatalyst utilizing blue light followed by oxidation of a radical abstractor reagent generates a radical that performs HAT on a hydrocarbon generating a carbon-centered radical. The radical undergoes oxidation by the Iridium-centered photocatalyst to generate the carbocation, which undergoes nucleophilic attack by various species. This Major Qualifying Project explores the potential of site-specific Csp3-H fluorination of aliphatic amino acids using the mechanism proposed by the Musacchio group. Future explorations include investigating the capacity for C-H functionalization of dipeptides and peptide chains, as well as radiolabeling aliphatic amino acids with 18F.

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