Boronic Acid Mediated Coupling of Catechols and N-Hydroxylamines: A Bioorthogonal Reaction to Label Peptides

Margaret K. Meadows, Emily K. Roesner, Vincent M. Lynch, Tony D. James, Eric V. Anslyn

Research output: Contribution to journalArticle

12 Citations (Scopus)
177 Downloads (Pure)

Abstract

An irreversible, three-component assembly with 2-formylphenylboronic acid, catechol, and N-hydroxylamines was achieved in aqueous media. The boronate ester product was formed with substituted catechols including l-DOPA. Assembly was found to be orthogonal to common biological functional groups and both copper(I)-catalyzed alkyne-azide cycloaddition and aminoether/carbonyl condensations. Boronate ester formation and aminoether condensation were achieved in one pot with a hexameric peptide.

Original languageEnglish
Pages (from-to)3179-3182
Number of pages4
JournalOrganic Letters
Volume19
Issue number12
Early online date5 Jun 2017
DOIs
Publication statusPublished - 16 Jun 2017

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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