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Rh(III)-Catalyzed Methodologies Applied to the Synthesis of Unnatural Peptides
Presented By: Christopher William Lamartina
Abstract:
Contemporary developments in the field of synthetic peptide methodologies are imperative for enabling the advance of drug design in medicinal chemistry. Rh(III)-catalyzed carboamidation methods which install C-C bonds and C-N bonds across readily available alkene substrates have been an underexplored avenue for peptide modification chemistry. In this thesis, several novel catalytic methodologies are disclosed which simultaneously install unnatural amino acid motifs during peptide ligation events. First, we report a modular ligation methodology that couples dioxazolones, arylboronic acids, and acrylamides to construct amide bonds in a diastereoselective manner. Next, we expanded this technology to the application of macrocyclic peptide synthesis with concomitant incorporation of noncanonical α-amino acids. Finally, we have explored a new hydroamidation mechanism as a complementary form of peptide macrocyclization.
