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Design, synthesis and biological evaluation of immunostimulating mannosylated desmuramyl peptides

Ribić, Rosana; Stojković, Ranko; Milković, Lidija; Antica, Mariastefania; Cigler, Marko; Tomić, Srđanka (2019) Design, synthesis and biological evaluation of immunostimulating mannosylated desmuramyl peptides. Beilstein Journal of Organic Chemistry, 15 . pp. 1805-1814. ISSN 1860-5397

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Muramyl dipeptide is the minimal structure of peptidoglycan with adjuvant properties. Replacement of the N-acetylmuramyl moiety and increase of lipophilicity are important approaches in the preparation of muramyl dipeptide analogues with improved pharmacological properties. Mannose receptors present on immunocompetent cells are pattern-recognition receptors and by mannose ligands binding they affect the immune system. Here we present the design, synthesis and biological evaluation of novel mannosylated desmuramyl peptide derivatives. Mannose was coupled to dipeptides containing a lipophilic adamantane on N- or C- terminus through a glycolyl or hydroxyisobutyryl linker. Adjuvant activities of synthesized compounds were investigated in the mouse model using ovalbumin as an antigen. Their activities were compared to the previously described mannosylated adamantane-containing desmuramyl peptide and peptidoglycan monomer. Tested compounds exhibited adjuvant activity and the strongest enhancement of IgG production was stimulated by compound 21 (Man-OCH2-ᴅ-(1-Ad)Gly-ʟ-Ala-ᴅ-isoGln).

Item Type: Article
Uncontrolled Keywords: adamantane ; adjuvant activity ; desmuramyl peptide ; mannose
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Molecular Biology
Division of Molecular Medicine
Depositing User: Lidija Milković
Date Deposited: 03 Oct 2019 14:05
DOI: 10.3762/bjoc.15.174

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