engleski

synthesis of multiantenNary mannose derived DESMURAMYL PEPTIDES

Muropeptides are fragments of peptidoglycans, unique polymers that build up the cell wall of bacteria. They are used as immunostimulating compounds (adjuvants). Muramyl dipeptide (MDP), N-acetylmuramyl-L-alanyl-D-isoglutamine, is the smallest structural unit of peptidoglycans showing the immunostimulating activity. Numerous MDP analogues lacking the hydrophilic carbohydrate moiety (desmuramyl peptides) with different groups at C- and N-terminus of the L- Ala-D-isoGln moiety have been synthesized. [1] We have designed and synthesized desmuramyl peptides with incorporated lipophilic adamantyl group and also their mannosylated derivatives. [2, 3] Attached mannose allows the targeting of cell surface receptors recognizing glycans on immune cells while adamantane group facilitates the anchoring of the peptidoglycan ‘cargo’ to the membrane. Synthesized desmuramyl peptides have been encapsulated into liposomes, vehicles often used for the target delivery. In these liposomal formulations adamantane group penetrates into the lipid bilayer while mannose is exposed at the liposome surface and can serve in targeting mannose receptors. [4] In order to improve lectin-carbohydrate binding we are developing methodology for the stereoselective synthesis of di- and tri- antennary mannose derivatives of desmuramyl peptides because increasing of mannose subunits number will enhance strength of overall mannose – lectin interactions.

DESMURAMYL PEPTIDES ; ADAMANTYL ; MANNOSYL

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