C - Chemistry – Metallurgy – 07 – H
Patent
C - Chemistry, Metallurgy
07
H
C07H 3/06 (2006.01) A61K 31/702 (2006.01) A61K 39/112 (2006.01) A61K 47/42 (2006.01) A61K 47/48 (2006.01) A61P 31/04 (2006.01) C07K 9/00 (2006.01) C07K 16/12 (2006.01) C12P 19/00 (2006.01)
Patent
CA 2434668
As part of a program for the development of synthetic vaccines against the pathogen Shigella flexneri, the conformational behavior of the O-specific polysaccharide (O-SP) of S. flexneri 5a and of four related synthetic pentasaccharide fragments was studied with a combination of NMR and molecular modeling methods. The NMR conformational analysis based on 1H and 13C chemical shifts analysis, inter-residue distances evaluation as well as one- and three-bond heteronuclear coupling constants measurements shows that the conformation of one of the four related pentasaccharides closely mimics the conformational features of the native O-SP in solution. Inhibition ELISA demonstrated that a protective monoclonal antibody specific for S. flexneri 5a shows a higher affinity for this pentasaccharide when compared with the others. A complete conformational search was carried out on the pentasaccharides using the CICADA algorithm interfaced with MM3 force field. Boltzman-averaged inter-residue distances and 3J C,H coupling constants were calculated for the different conformational families and compared to data obtained by NMR on all pentasaccharides. Experimental data are consistent with only one conformational family. From these informations, several models of the O-SP have been built with the molecular builder POLYS. The models in agreement with NMR data consist of right-handed helices presenting the branched glucosyl residue toward the external surface of their cylinder.
Baleux Francoise
Belot Frederic
Grandjean Cyrille
Mulard Laurence
Phalipon Armelle
Baleux Francoise
Belot Frederic
Grandjean Cyrille
Mulard Laurence
Phalipon Armelle
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