Fluorogenic Photo‐Crosslinking of Glycan‐Binding Protein Recognition Using a Fluorinated Azido‐Coumarin Fucoside

Author:

Bousch Cécile1,Vreulz Brandon1,Kansal Kartikey1,El‐Husseini Ali1,Cecioni Samy1ORCID

Affiliation:

1. Department of Chemistry Université de Montréal P.O. Box 6128, Station Downtown Montréal Québec H3 C 3 J7 Canada

Abstract

AbstractGlycan recognition by glycan‐binding proteins is central to the biology of all living organisms. The efficient capture and characterization of relatively weak non‐covalent interactions remains an important challenge in various fields of research. Photoaffinity labeling strategies can create covalent bonds between interacting partners, and photoactive scaffolds such as benzophenone, diazirines and aryl azides have proved widely useful. Since their first introduction, relatively few improvements have been advanced and products of photoaffinity labeling remain difficult to detect. We report a fluorinated azido‐coumarin scaffold which enables photolabeling under fast and mild activation, and which can leave a fluorescent tag on crosslinked species. Coupling this scaffold to an α‐fucoside, we demonstrate fluorogenic photolabeling of glycan‐protein interactions over a wide range of affinities. We expect this strategy to be broadly applicable to other chromophores and we envision that such “fluoro‐crosslinkers” could become important tools for the traceable capture of non‐covalent binding events.

Funder

Natural Sciences and Engineering Research Council of Canada

Fonds de recherche du Québec – Nature et technologies

Canada Foundation for Innovation

Publisher

Wiley

Subject

General Chemistry,Catalysis

Reference63 articles.

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