3 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

You might also like
Discover & Discuss Important Research

Keeping up-to-date with research can feel impossible, with papers being published faster than you'll ever be able to read them. That's where Researcher comes in: we're simplifying discovery and making important discussions happen. With over 19,000 sources, including peer-reviewed journals, preprints, blogs, universities, podcasts and Live events across 10 research areas, you'll never miss what's important to you. It's like social media, but better. Oh, and we should mention - it's free.

  • Download from Google Play
  • Download from App Store
  • Download from AppInChina

Researcher displays publicly available abstracts and doesn’t host any full article content. If the content is open access, we will direct clicks from the abstracts to the publisher website and display the PDF copy on our platform. Clicks to view the full text will be directed to the publisher website, where only users with subscriptions or access through their institution are able to view the full article.