Beilstein J Org Chem
Fachbereich Chemie and Konstanz Research School Chemical Biology (KoRS-CB), Universität Konstanz, 78457 Konstanz, Germany.
Published: September 2012
A series of six mono-, di-, and trivalent N,N'-diacetylchitobiose derivatives was conveniently prepared by employing a one-pot procedure for Cu(II)-catalyzed diazo transfer and Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) starting from commercially available amines. These glycoclusters were probed for their binding potencies to the plant lectin wheat germ agglutinin (WGA) from Triticum vulgaris by an enzyme-linked lectin assay (ELLA) employing covalently immobilized N-acetylglucosamine (GlcNAc) as a reference ligand. IC(50) values were in the low micromolar/high nanomolar range, depending on the linker between the two disaccharides. Binding enhancements β up to 1000 for the divalent ligands and 2800 for a trivalent WGA ligand, compared to N,N'-diacetylchitobiose as the corresponding monovalent ligand, were observed. Molecular modeling studies, in which the chitobiose moieties were fitted into crystallographically determined binding sites of WGA, correlate the binding enhancements of the multivalent ligands with their ability to bind to the protein in a chelating mode. The best WGA ligand is a trivalent cluster with an IC(50) value of 220 nM. Calculated per mol of contained chitobiose, this is the best WGA ligand known so far.
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http://dx.doi.org/10.3762/bjoc.8.91 | DOI Listing |
Bioorg Chem
June 2024
Institute of Chemical Process Fundamentals of the Czech Academy of Sciences, Rozvojová 1/135, CZ-165 00 Praha 6, Czech Republic. Electronic address:
Fluorination of carbohydrate ligands of lectins is a useful approach to examine their binding profile, improve their metabolic stability and lipophilicity, and convert them into F NMR-active probes. However, monofluorination of monovalent carbohydrate ligands often leads to a decreased or completely lost affinity. By chemical glycosylation, we synthesized the full series of methyl β-glycosides of N,N'-diacetylchitobiose (GlcNAcβ(1-4)GlcNAcβ1-OMe) and LacdiNAc (GalNAcβ(1-4)GlcNAcβ1-OMe) systematically monofluorinated at all hydroxyl positions.
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Department of Chemistry, Oklahoma State University, Stillwater, OK 74078-3071, United States. Electronic address:
In this study, a precursor carboxy-silica support was demonstrated in the immobilization of two different lectins, namely concanavalin A (Con A) and wheat germ agglutinin (WGA) for use in high performance lectin affinity chromatography (LAC) for the selective capturing and enrichment of glycoproteins from healthy/disease free and cancer human sera. The lectin columns thus obtained (i.e.
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Biodesign Center for Bioelectronics and Biosensors, Arizona State University, Tempe, Arizona 85287, United States.
Study interaction between ligands and protein receptors is a key step for biomarker research and drug discovery. In situ measurement of cell surface membrane protein binding on whole cells eliminates the cost and pitfalls associated with membrane protein purification. Ligand binding to membrane protein was recently found to induce nanometer-scale cell membrane deformations, which can be monitored with real-time optical imaging to quantify ligand/protein binding kinetics.
View Article and Find Full Text PDFPLoS One
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Department of Biological Sciences, Ohio University, Athens, Ohio, United States of America.
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View Article and Find Full Text PDFBioorg Chem
November 2022
Area for Molecular Function, Division of Material Science, Graduate School of Science and Engineering, Saitama University, Sakura, Saitama 338-8570, Japan; Medical Innovation Research Unit (MiU), Advanced Institute of Innovative Technology (AIIT), Saitama University, Sakura, Saitama 338-8570, Japan; Area for Health Science, Strategic Research Center, Saitama University, Sakura, Saitama 338-8570, Japan. Electronic address:
We synthesized N-acetylglucosamine-terminated hexavalent carbosilane dendrimers and investigated their binding to wheat germ agglutinin (WGA). The glycodendrimers were prepared by the conjugation of 3-mercaptopropyl, 4-mercaptobutyl, or 5‑mercaptopentyl glycosides to maleimide-terminated hexavalent carbosilane dendrimers. Titration of WGA with the glycodendrimers yielded quenching of tryptophan fluorescence.
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