Synthesis and Protective Anti-infective Action of Anomeric Lipophilic Glycosides of N-Acetylmuramyl-L-Alanyl-D-Isoglutamine

A. E. Zemlyakov^a,#, V. N. Tsikalova^a, V. V. Tsikalov^a, V. Ya. Chirva^a, E. L. Mulik^b, and O. V. Kalyuzhin^b

^# Phone: (065) 223-3885; fax: (065) 223-2310; e-mail: alex_z@crimea.edu
^a Vernadsky Tauric National University, pr. akademika Vernadskogo 4, Simferopol, Crimea, 95007 Ukraine
^b Research Institute of Human Morphology, Russian Academy of Medical Sciences, ul. Tsuryupy 3, Moscow, 117418 Russia

Received June 20, 2005; in final form, September 3, 2005

Abstract: Anomeric pairs of α- and β-dodecyl, α- and β-(1-pentylhexyl), and α- and β-cyclododecyl glycosides of N-acetylmuramyl-L-alanyl-D-isoglutamine (MDP) were synthesized. The starting β-D-glucosaminides were obtained by the oxazoline method, and the corresponding α-isomers, by the mercuric iodide–catalyzed glycosylation of alcohols with α-glucosaminyl chloride peracetate in nitromethane at ~90ºC. No reliable differences between the stimulation of mouse resistance to the infection with Staphylococcus aureus (doses of 2, 20, and 200 μg/mouse) and Escherichia coli (doses of 0.05, 1, and 20 μg/mouse) with the MDP α- and β-glycosides were found.

Key words: anti-infective resistance, glycopeptides, muramyldipeptide, muramyldipeptide glycosides

Russian Journal of Bioorganic Chemistry 2006, 32 (4):382-388