Glycobiology, 2002, Vol. 12, No. 4 241-250
© 2002 Oxford University Press
Solution structure of two xenoantigens: 
Gal-LacNAc and Gal-Lewis X
2Centre de Recherche sur les Macromolécules Végétales (Affiliated with Joseph Fourier University), BP 53, F-38041 Grenoble cedex 9, France; 3Departamento de Química, Universidad de La Rioja, Madre de Dios, 51, E-26006 Logroño (La Rioja), Spain; and 4Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, ul Miklukho-Maklaya 16/10, 17871 GSP-7, V-437, Moscow, Russia
Organ hyperacute rejection, a phenomenon occurring during discordant xenotransplantation, is due to the recognition of an oligosaccharide epitope by human xenoreactive natural antibodies. In addition to the 
Gal(1-3)ßGal(1-4)GlcNAc trisaccharide, a fucosylated structure, Gal-Lewis X, has been shown to be recognized by the antibodies. Both the trisaccharide and the tetrasaccharide have been synthesized by chemical methods. A complete nuclear magnetic resonance characterization of the two compounds has been performed, including the measurements of two-dimensional nuclear Overhauser effect spectroscopy data. Molecular dynamics simulations were run for several ns in the presence of explicit water molecules. The combination of experimental and theoretical approaches revealed the effect of an additional fucose residue on the conformational behavior of the xenoantigen. This branched fucose strongly rigidifies the N-acetyllactosamine. The effect on the Gal(1-3)Gal fragment is less marked. In the presence of fucose, the terminal Gal residue can still adopt two different conformations, but the equilibrium populations are modified.
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