Synthesis and biological activity of aryl S-β-glycosides of 1-thio-N-acetylmuramyl-L-alanyl-D-isoglutamine
- First Online:
- Cite this article as:
- Zemlyakov, A.E., Tsikalova, V.N., Azizova, L.R. et al. Russ J Bioorg Chem (2008) 34: 223. doi:10.1134/S106816200802012X
Phenyl, p-tolyl, and p-tert-butylphenyl β-1-thio-N-acetylglucosaminides were synthesized by the treatment of thiophenols with peracetate of α-D-glucosaminyl chloride in the presence of triethylamine or under the conditions of phase-transfer catalysis with quaternary ammonium salts. The compounds synthesized were used for obtaining of glycosides of 4,6-O-isopropylidene-N-acetylmuramic acid, which were coupled with L-Ala-D-Glu(NH2)-OBzl and then deprotected to obtain the target aryl β-thioglycosides of N-acetylmuramyl-L-analyl-D-isoglutamine (MDP). The aryl β-thioglycosides of MDP were found to stimulate an antibacterial resistance toward Staphylococcus aureus in mice. The reliable induction of the spontaneous activity of natural killers in the population of blood mononuclear cells was observed only for phenyl β-thio-MDP at a dose of 200 µg/ml.
Key wordsglycopeptidesantibacterial resistancearyl thioglycosidescytotoxicityglycosidesmuramyl dipeptide
N-acetylmuramyl-L-alanyl-D-isoglutamine (muramyl dipeptide)
mononuclear blood cells