| DOI | Trouver le DOI : https://doi.org/10.1016/j.carres.2008.01.007 |
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| Auteur | Rechercher : Pukin, Aliaksei V.; Rechercher : Weijers, Carel A. G.; Rechercher : van Lagen, Barend; Rechercher : Wechselberger, Rainer; Rechercher : Sun, Bin; Rechercher : Gilbert, Michel1; Rechercher : Karwaski, Marie-France1; Rechercher : Florack, Dion E. A.; Rechercher : Jacobs, Bart C.; Rechercher : Tio-Gillen, Anne P.; Rechercher : van Belkum, Alex; Rechercher : Endtz, Hubert P.; Rechercher : Visser, Gerben M.; Rechercher : Zuilhof, Han |
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| Affiliation | - Conseil national de recherches du Canada. Institut des sciences biologiques du CNRC
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| Format | Texte, Article |
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| Sujet | enzymatic synthesis; GM1 mimics; Guillain–Barré syndrome; NMR |
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| Résumé | Undec-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 α-(2→3)-sialyltransferase (CST-06) and β-(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–Barré syndrome. The synthesized compounds were analyzed by 1D and 2D 900 MHz NMR spectroscopy. TOCSY and DQF-COSY experiments in combination with 13C–1H correlation measurements (HSQC, HMBC) were carried out for primary structural characterization, and a complete assignment of all 1H and 13C chemical shifts is presented. |
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| Date de publication | 2008 |
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| Maison d’édition | Elsevier |
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| Dans | |
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| Langue | anglais |
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| Publications évaluées par des pairs | Oui |
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| Numéro du CNRC | PUKIN2008 |
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| Numéro NPARC | 9381545 |
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| Exporter la notice | Exporter en format RIS |
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| Signaler une correction | Signaler une correction (s'ouvre dans un nouvel onglet) |
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| Identificateur de l’enregistrement | c7b079aa-292b-404b-86c4-402a9015fbcc |
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| Enregistrement créé | 2009-07-10 |
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| Enregistrement modifié | 2020-04-15 |
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