Several types of polymeric glycoconjugates, N-substituted polyacrylamides, have been synthesized by the reaction of activated polymers with omega-aminoalkylglycosides: (i) (carbohydrate-spacer)n-polyacrylamide, 'pseudopolysaccharides'; (ii) (carbohydrate-spacer)n-phosphatidylethanolaminem-polyacrylamide, neoglycolipids, derivatives of phosphatidylethanolamine; (iii) (carbohydrate-spacer)n-biotin-polyacrylamide, biotinylated probes; (iv) (carbohydrate-spacer)n-polyacrylamide-(macroporous glass), affinity sorbents based on macroporous glass, covalently coated with polyacrylamide. An almost quantitative yield in the conjunction reaction makes it possible to insert in the conjugate a predetermined quantity of the ligand(s). Pseudopolysaccharides proved to be a suitable form of antigen for activation of polystyrene and poly(vinyl chloride) plates (ELISA) and nitrocellulose membranes (dot blot), being advantageous over traditional neoglycoproteins. Polyvalent glycolipids insert well in biological membranes: their physical properties, particularly solubility, can be changed in a desired direction. Biotinylated derivatives were used as probes for detection and analysis of lectins.

Blood group antigen-related oligosaccharides have been implicated in growth regulation, cell mobility control and adhesion; we are therefore interested in the localization of receptors for these oligosaccharides in tumour cells. Labelled neoglycoconjugates that carry synthetic sugar structures are suitable tools to determine: whether such binding sites are present in human lung cancer; whether structural alterations of the glycoligand part will affect extent of binding; and whether cell type-associated alterations can be detected. Sections from 121 cases of lung cancer, representing small cell and non-small cell lung carcinoma, mesothelioma and metastases from extrapulmonary primary carcinomas were used to study the binding of nine synthetic AH- and Le-related oligosaccharides. Probes with fucose-alpha 1-3/4-N-acetylglucosamine-beta 1-R, an A-like disaccharide and 3'-sulfated galactose as ligand appear to bind less well to small cell than to non-small cell lung cancer cases, whereas Lec-disaccharide distinguishes mesothelioma from metastatic carcinoma. The latter ligand, A-like disaccharide and H (type III)-like trisaccharide exhibit evident cell type-associated differences in extent of binding. Thus, tailor-made neoglycoconjugates constitute a promising class of histopathological tools that warrants further study.

High oligosnccharide specifciry for binding carbohydrate probes (biotinylated potyscrytamide wilh carbohydrates allached) with human hcmopoi. eiic and lymphoid cells is shown. Of 15 probes studied those bearing blood group trisaccharides, A and 13, bound most intensely. In addition, transformed (Icukemic and tymphoid) 4s interacted more strongly than normal ones.

Abstract. Mr= 311.83, triclinic, P1, a=7.3039 (9), b = 7.9432 (9), c = 13.4552 (8)/~, ct= 95.92 (1), fl = 98.66 (1), 7= 99.74 (1) °, V= 753.9 (2)/~3, Z= 2, D x = 1.374 g cm -3, Mo Kct radiation, 2 = 0.71069 ,/k, g= 3.90cm -1, F(000)= 328, room temperature, R = 0.037 for 2430 observed reflections. The CI atom is in an exo and the arylthio group in an endo orientation with respect to the norbornane framework, which has a synchro-twist conformation. Rather high twist angles are probably due to the additivity of the effects of substituents. The short intramolecular S... O distance of 2.643 (2) A corresponds to a secondary interaction and the C-S...O unit is nearly linear.

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