Synthesis and Protective Activity of β-Glycosides of N-Acetylmuramyl-L-Alanyl-D-Isoglutamine with Alkylalicyclic and Arylaliphatic Aglycons

The following glycosides of N-acetylmuramyl-L-alanyl-D-isoglutamine (MDP) were synthesized: beta -4-tert-butylcyclohexyl MDP, beta -2-(adamant-1-yl)ethyl MDP, beta -2,2-diphenylethyl MDP, and beta -2-(p-biphenyl) ethyl MDP. The starting peracetylated beta -N-acetylglucosaminides were prepared by the oxazoline method. They were converted into 4,6-O-isopropylidene-N-acetyl-D-muramic acids, which were coupled with L-Ala-D-Glu(NH sub(2))OBn. The target glycopeptides were obtained after their deprotection. The stimulation of the anti-infection resistance of mice against Staphylococcus aureus by the MDP glycosides was studied.