Beilstein J. Org. Chem.2019,15, 1805–1814, doi:10.3762/bjoc.15.174
present the design, synthesis and biological evaluation of novel mannosylated desmuramylpeptide 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 desmuramylpeptide 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).
Keywords: adamantane; adjuvant activity; desmuramylpeptide; mannose; Introduction
Dendritic cells capture and internalize invading pathogens. Pathogen-associated molecular patterns have been known for a long time to affect the immune system of
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Graphical Abstract
Figure 1:
Peptidoglycan fragments with immunostimulating properties.