[Synthesis and biological activity of aryl S-beta-glycosides of 1-thio-N-acetylmuramyl-L-alanyl-D-isoglutamine].
Phenyl, p-tolyl, and p-tert-butylphenyl beta-1-thio-N-acetylglucosaminides were synthesized by the treatment of thiophenols with peracetate of alpha-D-glucosaminyl chloride in the presence of triethylamine or under the conditions of phase-transfer catalysis with quaternary ammonium salts. The compounds synthesized were used for obtaining of glycosides of 4,6-O-isopropylidene-N-acetylmuramic acid, which were coupled with L-Ala-D-Glu(NH2)-OBzl and then deprotected to obtain the target aryl beta-thioglycosides of N-acetylmuramyl-L-alanyl-D-isoglutamine (MDP). The aryl beta-thioglycosides of MDP were found to stimulate an antibacterial resistance toward Staphylococcus aureus in mice. The reliable induction of the spontaneous activity of natural killers in the population of blood mononuclear cells was observed only for phenyl beta-thio-MDP at a dose of 200 microg/ml. The English version of the paper: Russian Journal of Bioorganic Chemistry, 2008, vol. 34, no. 2; see also http://www.maik.ru.
A E
AE
Zemliakov
V N
VN
Tsikalova
L R
LR
Azizova
V Ia
VIa
Chirva
E L
EL
Mulik
M V
MV
Shkalev
O V
OV
Kaliuzhin
M V
MV
Kiselevskiĭ
D000119:Acetylmuramyl-Alanyl-Isoglutamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D002478:Cells, Cultured; D018920:Coculture Techniques; D003603:Cytotoxins / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D007155:Immunologic Factors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D020014:K562 Cells; D007694:Killer Cells, Natural / Q000187:drug effects / Q000276:immunology; D007963:Leukocytes, Mononuclear / Q000166:cytology / Q000187:drug effects / Q000276:immunology; D051379:Mice; D018805:Sepsis / Q000382:microbiology / Q000517:prevention & control; D013203:Staphylococcal Infections / Q000382:microbiology / Q000517:prevention & control; D013211:Staphylococcus aureus; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D003603:Cytotoxins; D006027:Glycosides; D007155:Immunologic Factors; D000119:Acetylmuramyl-Alanyl-Isoglutamine; C040416:N-acetyl-thiomuramyl-alanyl-isoglutamine