Issue 16, 2011
From the journal:

Organic & Biomolecular Chemistry

Chemoenzymatic synthesis of biotin-appended analogues of gangliosidesGM2, GM1, GD1a and GalNAc-GD1a for solid-phase applications and improved ELISA tests

Aliaksei V. Pukin,a   Dion E. A. Florack,b   Denis Brochu,c   Barend van Lagen,a   Gerben M. Visser,a   Tom Wennekes,a   Michel Gilbertc  and  Han Zuilhof*a  

* Corresponding authors

a Laboratory of Organic Chemistry, Wageningen University, Dreijenplein 8, Wageningen, The Netherlands
E-mail: han.zuilhof@wur.nl
Fax: +31317484914
Tel: +31317482361

b Plant Research International, Droevendaalsesteeg 1, Wageningen, The Netherlands

c Institute for Biological Sciences, National Research Council Canada, 100 Sussex Drive, Ottawa, Ontario, Canada

Abstract

Biotinylated analogues of gangliosides GM2, GM1, GD1a and GalNAc-GD1a were synthesized in high yields using glycosyltransferases from Campylobacter jejuni. The presence of a biotin moiety in the aglycone part of these mimics allows for attachment of these materials onto various streptavidin-coated surfaces. Analysis of the interaction of biotin-appended GM1 with the B subunit of Escherichia coli heat-labile enterotoxin performed in a modified ELISA procedure shows the potential of this compound to replace the natural GM1 in toxin detection.

Graphical abstract: Chemoenzymatic synthesis of biotin-appended analogues of gangliosides GM2, GM1, GD1a and GalNAc-GD1a for solid-phase applications and improved ELISA tests

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Article information

DOI
https://doi.org/10.1039/C1OB00009H
Article type
Paper
Submitted
04 Jan 2011
Accepted
18 May 2011
First published
18 May 2011

Org. Biomol. Chem., 2011,9, 5809-5815

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Chemoenzymatic synthesis of biotin-appended analogues of gangliosides GM2, GM1, GD1a and GalNAc-GD1a for solid-phase applications and improved ELISA tests

A. V. Pukin, D. E. A. Florack, D. Brochu, B. van Lagen, G. M. Visser, T. Wennekes, M. Gilbert and H. Zuilhof, Org. Biomol. Chem., 2011, 9, 5809 DOI: 10.1039/C1OB00009H

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