GM3, GM2 and GM1 mimics designed for biosensing: chemoenzymatic synthesis, target affinities and 900MHz NMR analysis

Autor: C.A.G.M. Weijers, Rainer Wechselberger, Anne P. Tio-Gillen, Michel Gilbert, Bart C. Jacobs, Hubert P. Endtz, Dion E.A. Florack, Han Zuilhof, Bin Sun, Aliaksei V. Pukin, Alex van Belkum, Gerben M. Visser, Marie-France Karwaski, Barend van Lagen
Přispěvatelé: NMR-spectroscopie, Dep Scheikunde, Immunology, Neurology, Medical Microbiology & Infectious Diseases
Rok vydání: 2008
Předmět:
Magnetic Resonance Spectroscopy
crystalline silicon surfaces
Biosensing Techniques
Enterotoxin
medicine.disease_cause
Guillain–Barré syndrome
Biochemistry
Analytical Chemistry
campylobacter-jejuni
Biomimetic Materials
Gangliosides
one-pot synthesis
chemistry.chemical_classification
Molecular Structure
biology
Chemistry
extremely mild attachment
Cholera toxin
General Medicine
Nuclear magnetic resonance spectroscopy
Organische Chemie
enzymatic synthesis
PRI Bioscience
nuclear-magnetic-resonance
guillain-barre
Hydrophobic and Hydrophilic Interactions
Heteronuclear single quantum coherence spectroscopy
Cholera Toxin
cholera-toxin
Stereochemistry
Enzyme-Linked Immunosorbent Assay
Receptors
Cell Surface
Heat-labile enterotoxin
Campylobacter jejuni
medicine
Animals
Escherichia coli
heat-labile enterotoxin
VLAG
Organic Chemistry
Galactose
Glycoside
solid-phase
biology.organism_classification
GM1 mimics
NMR
Glucose
covalently attached monolayers
Cattle
Zdroj: Carbohydrate Research : an international journal 343 (2008) 4
Carbohydrate Research : an international journal, 343(4), 636-650
Carbohydrate Research, 343(4), 636-650. Elsevier
ISSN: 0008-6215
Popis: Undee-10-enyl, undec-10-ynyl and 11-azidoundecyl glycoside analogues corresponding to the oligosaccharides of human gangliosides GM3, GM2 and GM1 were synthesized in high yields using glycosyltransferases from Campylobacter jejuni. Due to poor water solubility of the substrates, the reactions were carried out in methanol-water media, which for the first time were shown to be compatible with the C. jejuni alpha-(2 -> 3)-sialyltransferase (CST-06) and beta-(1 -> 4)-N-acetylgalactosaminyltransferase (CJL-30). Bioequivalence of our synthetic analogues and natural gangliosides was examined by binding to Vibrio cholerae toxin and to the B subunit of Escherichia coli heat-labile enterotoxin. This bioequivalence was confirmed by binding mouse and human monoclonal antibodies to GM1 and acute phase sera containing IgM and IgG antibodies to GM1 from patients with the immune-mediated polyneuropathy Guillain-Barre syndrome. The synthesized compounds were analyzed by 1D and 2D 900 MHz NMR spectroscopy. TOCSY and DQF-COSY experiments in combination with C-13-H-1 correlation measurements (HSQC, HMBC) were carried out for primary structural characterization, and a complete assignment of all H-1 and C-13 chemical shifts is presented. (c) 2008 Elsevier Ltd. All rights reserved.
Databáze: OpenAIRE
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