Unprecedented Affinity Labeling of Carbohydrate-Binding
Proteins with s‑Triazinyl Glycosides
Posted on 2019-08-23 - 20:03
Carbohydrate–protein
interactions trigger a wide range of
biological signaling pathways, the mainstays of physiological and
pathological processes. However, there are an incredible number of
carbohydrate-binding proteins (CBPs) that remain to be identified
and characterized. This study reports for the first time the covalent
labeling of CBPs by triazinyl glycosides, a new and promising class
of affinity-based glycoprobes. Mono- and bis-clickable triazinyl glycosides
were efficiently synthesized from unprotected oligosaccharides (chitinpentaose
and 2′-fucosyl-lactose) in a single step. These molecules allow
the specific covalent labeling of chitin-oligosaccharide-binding proteins
(wheat germ agglutinin WGA and Bc ChiA1 D202A, an
inactivated chitinase) and fucosyl-binding lectin (UEA-I), respectively.
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Masselin, Arnaud; Petrelli, Antoine; Donzel, Maxime; Armand, Sylvie; Cottaz, Sylvain; Fort, Sébastien (2019). Unprecedented Affinity Labeling of Carbohydrate-Binding
Proteins with s‑Triazinyl Glycosides. ACS Publications. Collection. https://doi.org/10.1021/acs.bioconjchem.9b00432
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AUTHORS (6)
AM
Arnaud Masselin
AP
Antoine Petrelli
MD
Maxime Donzel
SA
Sylvie Armand
SC
Sylvain Cottaz
SF
Sébastien Fort
KEYWORDS
carbohydrate-binding proteinscovalentTriazinylGlycosideaffinity-based glycoprobesbis-clickable triazinyl glycosidesfucosyl-binding lectinfucosyl-lactoseUnprecedented Affinitypathwaychitinpentaosemoleculemainstaychitinasechitin-oligosaccharide-binding proteinsMonotriazinyl glycosidesinteractionBc ChiA 1 D 202ACarbohydrate-Binding Proteinsstudy reportswheat germ agglutinin WGAUEA-ICBP