Copper-mediated peptide arylation selective for the N-terminus

Mary K. Miller, Haopei Wang, Kengo Hanaya, Olivia Zhang, Alex Berlaga, Zachary T. Ball

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

Abstract

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 certaino-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.

Original languageEnglish
Pages (from-to)10501-10505
Number of pages5
JournalChemical Science
Volume11
Issue number38
DOIs
Publication statusPublished - 2020 Oct 14
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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