Glycosidase-catalysed synthesis of oligosaccharides: a one step synthesis of lactosamine and of the linear B type 2 trisaccharide α-d-Gal-(1→3)-β-d-Gal-(1→4)-β-d-GlcNAcSEt involved in the hyperacute rejection response in xenotransplantation from pigs to man and as the specific receptor for toxin A from Clostridium difficile

Abstract

Sequential use of the β-galactosidase from Bacillus circulans and an α-galactosidase from Aspergillus oryzae give the linear B trisaccharide 2, identified as the epitope that binds anti-Gal antibodies during pig-to-man xenotransplantation and as the receptor for toxin A from Clostridium difficile.

References

1. W. Parker, S. Saadi, S. S. Lin, Z. E. Holzknecht, M. Bustos and J. L. Platt, Immunology Today, 1996, 17, 373.
2. D. K. C. Cooper, E. Koren and R. Oriol, Immunological Rev., 1994, 141, 31.
3. G. F. Clark, H. C. Krivan, T. D. Wilkins and D. F. Smith, Arch. Biochem. Biophys., 1987, 257, 217.
4. G. Vic, M. Scigelova, J. J. Hastings, O. W. Howarth and D. H. G. Crout, Chem. Commun., 1996, 1473.
5. C.-H. Wong, S. L. Haynie and G. M. Whitesides, J. Org. Chem., 1982, 47, 5416; C.-H. Wong, R. Wang and Y. Ichikawa, J. Org. Chem., 1992, 57, 4343.
6. J. Thiem and T. Wiemann, Synthesis, 1992, 141.
7. A. Zervosen and L. Elling, J. Am. Chem. Soc., 1996, 118, 1836.
8. K. Sakai, R. Katsumi, H. Ohi, T. Usui and Y. Ishido, J. Carbohydr. Chem., 1992, 11, 553.
9. T. Buska, P. J. Garreg, P. Kondarsson and J. L. Maloisel, Tetrahedron: Asymmetry, 1994, 5, 2187.
10. G. Vic, J. J. Hastings, O. W. Howarth and D. H. G. Crout, Tetrahedron: Asymmetry, 1996, 7, 709.