engleski

SYNTHESIS OF MANNOSYLATED FERROCENE ESTER DERIVATIVES OF DESMURAMYL DIPEPTIDE

Immune adjuvants are added to vaccines in order to enhance the immune response to an antigen. Muramyl dipeptide (MDP, N-acetylmuramyl-L-alanyl-D- isoglutamine) is the smallest peptidoglycan fragment able to trigger the immune response.[1] Structural modification of MDP and its analogues, such as desmuramyl dipeptide (DMP), have been performed in order to prepare derivatives with an improved immune responce. In our previous research we reported the synthesis and immunostimulatory activity of mannosylated adamantane derivatives of DMP which showed enhanced immunostimulatory activity compared to compounds without the mannose subunit.[2] In this work we described the synthesis of novel class of DMP derivatives in which lipophilic ferrocene unit was introduced at C-terminus of L-Ala-D-iGln via ester bond, followed by mannosylation of N-terminus through glycolyl spacer. Alkyl spacers of different length (2-5 C atoms) were introduced between DMP and ferrocene unit to further increase lipophilicity of the synthesized compounds and to study its impact on biological activity.

desmuramyl dipeptide ; ferrocene ; immunostimulatory activity ; mannose

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