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

10 Citations (Scopus)
113 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

Fingerprint

Hydroxylamines
Catechols
Boronic Acids
peptides
Labels
esters
Condensation
Esters
condensation
assembly
Peptides
acids
Alkynes
Azides
Cycloaddition
Cycloaddition Reaction
cycloaddition
alkynes
Functional groups
Copper

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Boronic Acid Mediated Coupling of Catechols and N-Hydroxylamines : A Bioorthogonal Reaction to Label Peptides. / Meadows, Margaret K.; Roesner, Emily K.; Lynch, Vincent M.; James, Tony D.; Anslyn, Eric V.

In: Organic Letters, Vol. 19, No. 12, 16.06.2017, p. 3179-3182.

Research output: Contribution to journalArticle

Meadows, Margaret K. ; Roesner, Emily K. ; Lynch, Vincent M. ; James, Tony D. ; Anslyn, Eric V. / Boronic Acid Mediated Coupling of Catechols and N-Hydroxylamines : A Bioorthogonal Reaction to Label Peptides. In: Organic Letters. 2017 ; Vol. 19, No. 12. pp. 3179-3182.
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