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

Abstract

The following glycosides of N -acetylmuramyl-L -alanyl-D -isoglutamine (MDP) were synthesized: β -4-tert -butylcyclohexyl MDP, β -2-(adamant-1-yl)ethyl MDP, β -2,2-diphenylethyl MDP, and β -2-( p -biphenyl)ethyl MDP. The starting peracetylated β -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 2 )OBn. The target glycopeptides were obtained after their deprotection. The stimulation of the antiinfection resistance of mice against Staphylococcus aureus by the MDP glycosides was studied.

Secondary structure of muramyl dipeptide glycoside in pristine state and immobilized on nanosilica surface

“…Moreover, ion-molecule reactions of molecular ion can in some extend model the reaction pathways of thermally stimulated reactions as well as biotransformation pathways of MDP in the natural conditions. Chemical structure and stability of MDP O-glycoside during storage have been confirmed by electrospray mass spectrometry (Figure 1) and 1 H-NMR [41].…”

“…О-{(4-tert-butylcyclohexyl)-2-acetamido-2,3-dideoxy-βd-glucopyranoside-3-yl}-D-lactoyl-L-alanyl-D-isoglutamine (MDP О-glycoside , the scheme 1) was kindly gifted by the Department of Biological and Organic chemistry of Taurida National V.I. Vernadsky University [40,41]. Sample of MDP Оglycoside with a concentration of 0.6 mmol/g of on the silica surface was obtained by impregnation.…”