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Open AccessExtended Abstract

Design and Synthesis of Immunostimulating Mannosylated Muropeptide Analogs Containing 2-Aminoadamantane-2-carboxylic Acid

Department of Nursing, University Center Varaždin, University North, Jurja Križanića 31b, HR-42000 Varaždin, Croatia
Department of Chemistry, Josip Juraj Strossmayer University of Osijek, Cara Hadrijana 8/A, HR-31000 Osijek, Croatia
Faculty of Science, University of Zagreb, Horvatovac 102a, HR-10000 Zagreb, Croatia
Author to whom correspondence should be addressed.
Presented at the 2nd Molecules Medicinal Chemistry Symposium (MMCS): Facing Novel Challenges in Drug Discovery, Barcelona, Spain, 15–17 May 2019.
Proceedings 2019, 22(1), 69;
Published: 13 August 2019
(This article belongs to the Proceedings of The Molecules Medicinal Chemistry Symposium)
PDF [190 KB, uploaded 13 August 2019]


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. Numerous MDP derivatives were synthesized with the aim to avoid MDP unwanted side-effects. Many of them have therapeutic potential, including clinical use. A very important parameter in the improvement of pharmacological properties of MDP is lipophilicity, e.g., it eliminates drawbacks caused by poor macrophage penetration and rapid elimination. On the other side, mannose receptors (MR), present on immunocompetent cells (such as macrophages and dendritic cells), are considered to be pattern-recognition receptors and responsible for the binding, among others, of mannosylated antigens or relevant biologically active molecules containing mannose, thus affecting the immune reactions. Up to now, our research was directed towards desmuramyl peptides which contain adamantylglycine and mannosylated adamantylglycine moieties bound to the essential part of MDP, l-Ala-d-isoGln. Here, we present the design and synthesis of novel mannosylated muropeptide analogs containing 2-aminoadamantane-2-carboxylic acid. Prepared desmuramyl peptides have lipophilic 2-aminoadamantane-2-carboxylic acid attached at the N-terminus of desmuramy dipeptide core and mannose connected to the tripeptide over a glycolyl linker. Immunostimulating activities of prepared compounds will be evaluated in the mice model using ovalbumin as an antigen and compared with previously prepared derivatives.
Keywords: adamantane; adjuvant; mannose; muramyl dipeptide adamantane; adjuvant; mannose; muramyl dipeptide
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Ribić, R.; Paurević, M.; Tomić, S. Design and Synthesis of Immunostimulating Mannosylated Muropeptide Analogs Containing 2-Aminoadamantane-2-carboxylic Acid. Proceedings 2019, 22, 69.

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