Collect. Czech. Chem. Commun. 1998, 63, 590-598
https://doi.org/10.1135/cccc19980590

Synthesis and Immunomodulating Activity of Lipophilic Analogs of N-Acetylnormuramoyl-L-2-aminobutanoyl-D-isoglutamine

Miroslav Ledvinaa, Jan Ježeka, David Šamana and Věra Hříbalováb

a Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic,166 10, Prague 6, Czech Republic
b National Institute of Public Health, 100 42 Prague 10, Czech Republic

Abstract

N-Acetylnormuramoyl-L-2-aminobutanoyl-D-isoglutamine (7) and its lipophilic 6-O-octadecanoyl (8) and 6-O-(2-tetradecylhexadecanoyl) (9) derivatives were prepared and their immunoadjuvant activity and pyrogenicity were tested. Compounds 8 and 9 are less pyrogenic than muramoyl-dipeptide (MDP) and norMDP analog 7. Both lipophilic derivatives 8 and 9 are better adjuvants than MDP in cell mediated immunity.

Keywords: Carbohydrates; Glycosides; Aminosugars; Muramyl glycopeptides; Immunoadjuvants.