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Miller, Mary K.; Wang, Haopei; Hanaya, Kengo; Zhang, Olivia; Berlaga, Alex; Ball, Zachary T. (, Chemical Science)null (Ed.)Polypeptides present remarkable selectivity challenges for chemical methods. Amino groups are ubiquitous in polypeptide structure, yet few paradigms exist for reactivity and selectivity in arylation of amine groups. This communication describes the utilization of boronic acid reagents bearing certain o -electron withdrawing groups for copper-mediated amine arylation of the N-terminus under mild conditions and primarily aqueous solvent. The method adds to the toolkit of boronic acid reagents for polypeptide modification under mild conditions in water that shows complete selectivity for the N-terminus in the presence of lysine side chains.more » « less
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Miller, Mary K.; Ball, Zachary T. (, Israel Journal of Chemistry)Abstract Transition‐metal catalysis provides new approaches to selectivity and the activation of otherwise inert functional groups. Bioconjugation with protein and peptide substrates presents numerous challenges of functional group activation and selectivity, and transitional‐metal approaches provide important alternative solutions to these challenges. This article describes the development of boronic acid reagents for new selective approaches to modification of peptides and proteins, focusing primarily on catalytic C−X bond formation.more » « less
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