AMP deaminase in vitro inhibition by xenobiotics A potential molecular method for risk assessment of synthetic nitro- and polycyclic musks, imidazolium ionic liquids and N-glucopyranosyl ammonium salts.

The usefulness of in vitro AMP deaminase inhibition was examined as a potential molecular method in risk assessment of xenobiotics. The enzyme participates in the principal purine nucleotide interconversion and degradation pathways, and its absence caused perturbations in the cellular ATP pool. The compounds selected were synthetic musks with a known negative environmental impact and the toxicologically unknown ionic liquids and N-glucopyranosyl ammonium bromides, which have recently attracted much interest from the chemical and related industries. All the compounds tested demonstrated a dose-dependent inhibition of AMP deaminase activity. IC(50) ranged from 0.3µM for polycyclic musks to 500µM for N-glucopyranosyl trimethylammonium bromide. Analysis of Dixon plots showed the inhibition type for all the compounds to be noncompetitive. The results support the choice of such an assay for the prospective risk assessment of these compounds.

Crystal structure of N-(tri-O-acetyl-alpha-D-xylopyranosyl)pyridinium bromide.

The structure of N-(2,3,4-tri-O-acetyl-alpha-D-xylopyranosyl)pyridinium bromide was determined by X-ray crystallography and 1H NMR spectroscopy. Two xylopyranosyl moieties crystallize with three water molecules and there is a novel pattern of Br(-) and H(2)O contacts. Both xylopyranosyl rings in the asymmetric unit have the 1C(4) conformation, with all three axial O-Ac groups.

Molecular and crystal structures of N-(beta-D-galactopyranosyl)pyridinium bromide and its per-O-acetylated derivative.

1H NMR spectroscopy and X-ray diffraction data are described for N-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)pyridinium bromide and N-(beta-D-galactopyranosyl)pyridinium bromide. X-ray crystallography revealed that the O-acetylated salt crystallizes with two molecules of water and one molecule of ethanol.

Preparation, chemical and crystal structures of N-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyl)pyridinium chloride.

Preparation and isolation of N-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyl)pyridinium chloride are described. Its structure was determined by 1H NMR spectroscopy and X-ray analysis. X-ray crystallography revealed that the salt crystallizes with one molecule of water. Ab initio calculations were used to determine charges on atoms in the cation of the title compound.