Ingrid 't Hart

100 Chapter 5 5 provide Hep-GM3, Hep-GM2 and Hep-GM1. The four heptosyl-ganglioside mimics will be immobilized on NHS-ac�vated microarray slides, along with the corresponding ganglioside oligosaccharides. Serum an�bodies from GBS pa�ents will be screened for binding towards these gangliosides and mimics to provide insight in the effect of heptoside to trigger cross reac�ve an�bodies during C. jejuni infec�on and triggering GBS.provide Hep-GM3, Hep-GM2 and Hep-GM1. The four heptosyl-ganglioside mimics will be immobilized on NHS-ac�vated microarray slides, along with the corresponding ganglioside oligosaccharides. Serum an�bodies from GBS pa�ents will be screened for binding towards these gangliosides and mimics to provide insight in the effect of heptoside to trigger cross reac�ve an�bodies during C. jejuni infec�on and triggering GBS. Experimental sec�on Chemical synthesis NMR nomenclature The monosaccharides of C. jejuni core heptose-ganglioside mimics have been labeled as shown in Figure S1. Star�ng from the reducing end these were labeled Hep-I, Gal-II, Neu5Ac-III, GalNAc-IV and Gal-V. Figure S1 . Monosaccharide labeling system for heptose-ganglioside mimics. Experimental procedures 2,2,2-Trichloroace�midate 2,3,4,6-tetra- O -benzoyl-α-D-galactopyranoside (5). Compound 5 was synthesized from galactose as described before (Chapter 4: 5). 29 N -(Benzyl)-benzyloxycarbonyl-5-aminopentyl 2,6,7-tetra- O -benzyl-4- O -(2-naphthyl) methyl-L- glycero -α-D- manno heptopyranoside (6). Compound 6 was synthesized in similar fashion as reported for α-D-mannosopyranoside. 27,28 1 H NMR (600 MHz, CDCl 3 ) δ 7.82 – 7.70 (3H, m, H-Ar), 7.48 – 7.03 (29H, m, H-Ar), 5.16 (2H, d, J = 20.7 Hz, CH 2 ), 5.02 (1H, d, J = 11.3 Hz, CH H ), 4.94 (1H, d, J = 10.8 Hz, H-1), 4.83 (1H, d, J = 11.9 Hz, CH H ), 4.79 (1H, d, J = 10.9 Hz, CH H ), 4.56 – 4.41 (6H, m, 3 x CH 2 ), 4.16 (1H, t, J = 6.1 Hz, H-6), 4.06 – 3.99 (1H, m, H-3), 3.92 (1H, t, J = 9.4 Hz, H-4), 3.81 (1H, s, CH H , OH O O O OH O HO HO HO HO O O NH 2 O HO HO HO OH NHAc HOOC O HO OH O AcHN O HO OH HO HO I II III IV V O BzO OBz BzO BzO O CCl 3 NH OBn O BnO BnO NapO HO O NBnCbz