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

doi:10.1021/acs.orglett.7b01198

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

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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 language	English
Pages (from-to)	3179-3182
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	12
Early online date	5 Jun 2017
DOIs	https://doi.org/10.1021/acs.orglett.7b01198
Publication status	Published - 16 Jun 2017

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.7b01198

Boronic Acid-Mediated Coupling of Catechols and N-Hydroxylamines
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.7b01198
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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.",

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AU - Lynch, Vincent M.

AU - James, Tony D.

AU - Anslyn, Eric V.

PY - 2017/6/16

Y1 - 2017/6/16

N2 - 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.

AB - 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.

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

Abstract

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