Organic Letters
Organic Letters
5 years ago

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

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

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01198

DOI: 10.1021/acs.orglett.7b01198

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