Selective Labeling of Carbohydrate-Binding Proteins by Triazinyl-Glycosides

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1st EuroCarb Young Researcher (ECYR) Workshop

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Mini symposium: Glycobiology at the LUMC and beyond

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Selective Labeling of Carbohydrate-Binding Proteins by Triazinyl-Glycosides

Arnaud Masselin 1 , Antoine Rousseau 1 , Sylvie Armand 1 , Sylvain Cottaz 1 , Sebastien Fort 1

1 CERMAV, Grenoble Cedex 9, France

With the availability of complete genome sequences for numerous prokaryotic and eukaryotic organisms, the number of novel genes in need of functional assignment increases dramatically. Chemical probes for selective covalent labeling of proteins are thus of great interest for the isolation of biological receptors or functional characterization of putative enzymes [1]. Photoaffinity-based probes and mechanism-based inhibitors are among the most investigated means to isolate target proteins. However, because of the difficulties associated with the synthesis and manipulation of oligosaccharides, most of the examples reported to date concern mono-and di-saccharide derivatives.

In the present work, we report a novel class of carbohydrate probes i.e oligosaccharidic triazinyl glycosides allowing the selective labeling of lectins and CAZymes. Triazinyl glycosides can be efficiently obtained from unprotected carbohydrates in aqueous media [2]; they can also be chemically modified with two bioorthogonal reporters [3]. As an illustration, we will describe the synthesis of chitinpentaose-based probes and their evaluation against Wheat Germ Agglutinin, Bacillus circulans chitinase A1 and Hen Egg White Lysozyme. In particular, an activity-based probe allowing both continuous fluorescence detection of chitinase activity by FRET and protein labeling will be presented.

Figure 1.Selective labeling of carbohydrate binding proteins by triazinyl-glycosides.

Stubbs K. A. Carbohydr. Res. 2014, 390, 9-19.

Noguchi, M.; Nakamura, M.; Ohno, A.; Tanaka, T.; Kobayashi, A.; Ishihara, M.; Fujita, M.; Tsuchida, A.; Mizuno, M.; Shoda, S. A Chem. Commun. 2012, 48(45), 5560–5562.

Li, H.; Zhou, H.; Krieger, S.; Parry,J. J.; Whittenberg,J. J.; Desai,A. V.; Rogers, B. E.; Kenis, P. J. A.; Reichert, D. E. Bioconjugate Chem. 2014, 25(4), 761–772.

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