Zemliakov A E, Tsikalova V N, Tsikalov V V, Chirva V Ia, Mulik E L, Kaliuzhin O V
Bioorg Khim. 2006 Jul-Aug;32(4):424-31.
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.
合成了N-乙酰胞壁酰-L-丙氨酰-D-异谷氨酰胺（MDP）的α-和β-十二烷基、α-和β-（1-戊基己基）以及α-和β-环十二烷基糖苷的端基异构体对。起始的β-D-葡糖胺苷通过恶唑啉法获得，相应的α-异构体则通过在-90℃下于硝基甲烷中用全乙酰化的α-葡糖胺酰氯与醇进行碘化汞催化的糖基化反应得到。未发现MDP的α-和β-糖苷在刺激小鼠抵抗金黄色葡萄球菌感染（剂量为2、20和200微克/小鼠）和大肠杆菌感染（剂量为0.05、1和20微克/小鼠）方面存在可靠差异。
