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

AV Pukin, CAGM Weijers, B van Lagen, R Wechselberger, B Sun, M Gilbert, MF Karwaski, DEA Florack, B.C. Jacobs, Anne Gillen, Alex Belkum, Hubert Endtz, GM Visser, H Zuilhof

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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.
Original languageUndefined/Unknown
Pages (from-to)636-650
Number of pages15
JournalCarbohydrate Research
Issue number4
Publication statusPublished - 2008

Research programs

  • EMC MM-02-72-02
  • EMC MM-04-28-01
  • EMC MM-04-44-02

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