engleski

Various synthetic pathways in the preparation of mannose conjugates

As the component of the outer cell membranes glycoproteins are an intracellular recognition determining factor. They participate in the control of cell growth, act as enzymes or hormones and are responsible for specific immunoreactions.1, 2 It is known that some cell membranes contain receptors for carbohydrate ligands. Lectins represent a very important group of proteins which exhibit specific affinity for different monosaccharides such as mannose, galactose, N-acetylglucosamine and N- acetylmannosamine.2 The aim of our work is to prepare compounds that contain a sugar part (mannose) connected to some biologically active molecule (peptidoglycan-monomer ; PGM ; adamantanamine, AMA) using various chain arms (chiral β -hydroxyacids such as (R)- and (S)-3- hydroxy-2-methylpropionic acid). The trichloroacetimidate and the Koenigs-Knorr method were both used to obtain O-glycosidic bond between hydroxyl group of the chain arm and the monosaccharide itself.2, 3 Several methods were tested for the formation of amide bond between O- glycoside and biologically active molecules using active ester method. The final purpose of this work would be to study possible changes and/or enhancement of biological activity of biomolecules linked to the cell surface by a sugar part of prepared conjugates. [1] H. Kunz, Angew. Chem., Int. Ed. Engl. 26 (1987) 249-308. [2] T. K. Lindhorst, Essentials of Carbohydrate Chemistry and Biochemistry, Wiley-VCH, Weinheim, 2003, 79- 90. [3] R. R. Schmidt, Amgew. Chem. Int. Ed. Engl. 25 (1986) 212-235.

mannose ; O-glycosidic bond

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