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.

This report represents the work of one or more WPI undergraduate students submitted to the faculty as evidence of completion of a degree requirement. WPI routinely publishes these reports on its website without editorial or peer review.

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