Unprecedented Affinity Labeling of Carbohydrate-Binding Proteins with s‑Triazinyl Glycosides
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 t...
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| Published in | Bioconjugate chemistry Vol. 30; no. 9; pp. 2332 - 2339 |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
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American Chemical Society
18.09.2019
Amer Chemical Soc |
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| Abstract | 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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| AbstractList | 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. 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 ChiA1 D202A, an inactivated chitinase) and fucosyl-binding lectin (UEA-I), respectively. |
| Author | Fort, Sébastien Cottaz, Sylvain Petrelli, Antoine Donzel, Maxime Armand, Sylvie Masselin, Arnaud |
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| Keywords | PHOTOAFFINITY PROBES OLIGOSACCHARIDES N-ACETYLCHITOHEXAOSE CHITINASE A1 IDENTIFICATION PHOTOPROBES DERIVATIVES RESIDUES SYMBIOSIS CHLORIDE |
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| Snippet | Carbohydrate–protein interactions trigger a wide range of biological signaling pathways, the mainstays of physiological and pathological processes. However,... Carbohydrate-protein interactions trigger a wide range of biological signaling pathways, the mainstays of physiological and pathological processes. However,... |
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| SubjectTerms | Affinity Affinity labeling Binding Biochemical Research Methods Biochemistry & Molecular Biology Carbohydrates Chemical Sciences Chemistry Chemistry, Multidisciplinary Chemistry, Organic Chitin Chitinase Glycosides Labeling Lactose Life Sciences Life Sciences & Biomedicine Medicinal Chemistry Oligosaccharide-binding proteins Oligosaccharides Physical Sciences Protein interaction Proteins Science & Technology Wheat Wheat germ Wheat germ agglutinin |
| Title | Unprecedented Affinity Labeling of Carbohydrate-Binding Proteins with s‑Triazinyl Glycosides |
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