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Synthesis and immunostimulating activity of novel mannosylated desmuramyl peptides

Peptidoglycan fragments of well defined structures, the best known of which are muramyl peptides, have been extensively studied as possible adjuvants for human and animal vaccines. Muramyl dipeptide (MDP, N- acetylmuramyl-L-alanyl-D-isoglutamine) is known as the smallest synthetic adjuvant molecule capable of replacing whole Mycobacteria in Freund’s adjuvant.1 Mannose receptors (MR), present on immunocompetent cells (such as macrophages and dendritic cells) are considered to be pattern- recognition receptors biding compounds with mannose, N-acetylglucosamine or fucose as their essential parts. Therefore, they are responsible for the binding, among others, of mannosylated antigens or relevant biologically active molecules containing mannose, thus affecting the immune reactions.2 Up to now our research in the field of potential adjuvants was directed towards desmuramyl peptides which contain adamantylglycine and mannosylated adamantylglycine moieties bound to the essential part of MDP, L-Ala-D-isoGln.3 Here we present synthesis and biological evaluation of novel mannosylated desmuramyl peptides containing glycolyl linker. Investigation of their immunostimulating activity was conducted in vivo in mouse model using ovalbumin as an antigen. Synthesized glycopeptides showed improved immunological activity than previously described mannosylated desmuramyl peptides with (R)- hydroxyisobutyl linker.

desmuramyl peptides ; mannose ; immunostimulating activity

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