title: [Synthesis and protective anti-infective action of anomeric lipophilic glycosides of N-acetylmuramyl-L-alanyl-D-isoglutamine].
abstract: Anomeric pairs of alpha- and beta-dodecyl, alpha- and beta-(1-pentylhexyl), and alpha- and beta-cyclododecyl glycosides of N-acetylmuramyl-L-alanyl-D-isoglutamine (MDP) were synthesized. The starting beta-D-glucosaminides were obtained by the oxazoline method, and the corresponding alpha-isomers, by the mercuric iodide-catalyzed glycosylation of alcohols with alpha-glucosaminyl chloride peracetate in nitromethane at -90 degrees C. No reliable differences between the stimulation of mouse resistance to the infection with Staphylococcus aureus (doses of 2, 20, and 200 microg/mouse) and Escherichia coli (doses of 0.05, 1, and 20 microg/mouse) with the MDP alpha- and beta-glycosides were found.
authors.forename: A E
authors.initials: AE
authors.lastname: Zemliakov
authors.forename: V N
authors.initials: VN
authors.lastname: Tsikalova
authors.forename: V V
authors.initials: VV
authors.lastname: Tsikalov
authors.forename: V Ia
authors.initials: VIa
authors.lastname: Chirva
authors.forename: E L
authors.initials: EL
authors.lastname: Mulik
authors.forename: O V
authors.initials: OV
authors.lastname: Kaliuzhin
mesh_terms: D000119:Acetylmuramyl-Alanyl-Isoglutamine / Q000031:analogs & derivatives*; D000276:Adjuvants, Immunologic / Q000138:chemical synthesis / Q000737:chemistry / Q000627:therapeutic use*; D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000627:therapeutic use*; D006027:Glycosides / Q000138:chemical synthesis / Q000737:chemistry / Q000627:therapeutic use*; D051379:Mice; D013203:Staphylococcal Infections / Q000517:prevention & control*; D013211:Staphylococcus aureus
chemical_list: D000276:Adjuvants, Immunologic; D000900:Anti-Bacterial Agents; D006027:Glycosides; D000119:Acetylmuramyl-Alanyl-Isoglutamine