[A short path to synthesis of 4-deoxy-4-fluoroglucosaminides: methylumbelliferyl N-acetyl-4-deoxy-4-fluoro-beta-D-glucosaminide].

A convenient method of synthesis of 1,6-anhydro-4-deoxy-2-O-tosyl-4-fluoro-beta-D-glucopyranose by fusion of 1,6;3,4-dianhydro-2-O-tosyl-beta-D-galactopyranose with 2,4,6-trimethylpyridinium fluoride was found. By successive action of ammonia, methyl trifluoroacetate, and acetic anhydride, the resulting compound was transformed into 1,6-anhydro-3-O-acetyl-2,4-dideoxy-2-trifluoroacetamido-4-fluoro-beta-D-glucopyranose, which was converted into 3,6-di-O-acetyl-2,4-dideoxy-2-trifluoroacetamido-4-fluoro-alpha-D-glucopyranosyl fluoride by the reaction with HF/Py. The resulting fluoride was further used as a glycosyl donor in the synthesis of methylumbelliferyl N-acetyl-4-deoxy-4-fluoro-beta-D-glucosaminide.

[Effects of mannose derivatives on development of selectin-dependent peritoneal inflammation in rats and mice].

The inhibitory effect of mannose-containing oligosaccharides on model carbohydrate ligand interaction with E-, P- and L-selectins in vitro, as well as on the ability of these compounds to block the leukocyte extravasation in rat and mouse peritonitis in vivo was studied. The monomeric and polymeric compounds, 4-nitrophenylthiomannoside, phenylmannoside, conjugated with polyacrylic acid, and alpha-mannose, conjugated with polyacrylamide, inhibited the binding of the model ligand to P- and L-selectins (but not to E-selectin). Intravenous injection of these compounds was found to cause a dose-dependent reduction of neutrophil accumulation in rat peritoneum.

[Synthesis of beta-maltosides, derivatives of p-nitrophenol, 2-chloro-4-nitrophenol, and 4-methylumbelliferone, and their use as substrates for determining alpha-glucosidase activity].

Synthesis of beta-maltosides, p-nitrophenyl-beta-D-maltoside and 4-methylumbelliferyl-beta-D-maltoside, based on interaction of hepta-acetate-beta-D-maltosyl fluoride with the corresponding trimethylsilyl ethers of p-nitrophenol and 4-methylumbelliferone is described. 2-Chloro-4-nitrophenyl-beta-D-maltoside was synthesized by interaction of hepta-acetate-alpha-D-maltosyl bromide with 2-chloro-4-nitrophenol in two phase system using phase transfer catalyst. The method of assay of neutral alpha-glucosidase from human kidney and urine using synthesized beta-maltosides (p-nitrophenyl-beta-D-maltoside, 2-chloro-4-nitrophenyl-beta-D-maltoside and 4-methylumbelliferyl-beta-D-maltoside) as substrates and beta-glucosidase as an auxiliary enzyme is proposed.

[Selective N-heterylazimine inhibition of reactions catalyzed by rat liver glutathione transferase].

Three reactions (nucleophile substitution, thiolysis and N-deoxygenation) catalyzed by rat liver glutathione transferase have been studied using several N-heterylazimine inhibitors. The inhibitors are sharply different in their effectiveness in the transferase reactions. Their efficiency depends on their structure.