[Synthesis and protective activity of beta-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 3-2-(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(NH2)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. The English version of the paper: Russian Journal of Bioorganic Chemistry, 2005, vol. 31, no. 6; see also http://www.maik.ru.
Zemliakov
A E
AE
Tsikalova
V N
VN
Tsikalov
V V
VV
Chirva
V Ia
VIa
Mulik
E L
EL
Kaliuzhin
O V
OV
D000119:Acetylmuramyl-Alanyl-Isoglutamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology; D000276:Adjuvants, Immunologic / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D024881:Drug Resistance, Bacterial; D006027:Glycosides / Q000138:chemical synthesis* / Q000494:pharmacology; D051379:Mice; D013203:Staphylococcal Infections / Q000276:immunology* / Q000382:microbiology; D013211:Staphylococcus aureus
D000276:Adjuvants, Immunologic; D006027:Glycosides; D000119:Acetylmuramyl-Alanyl-Isoglutamine