J. Verhoeven, R. Schwyzer
Nov 1, 1972
Citations
0
Influential Citations
9
Citations
Journal
Helvetica chimica acta
Abstract
The synthesis of methyl 2-acetamido-6-O-(N-methyl-isonicotinylium)-2-deoxy-β-D-glucopyranoside ion (2; iodide and chloride) is reported. Association with hen-egg-white lyso zyme causes chemical shift changes for its acetamido and glycosidic methyl groups comparable to those observed for the monosaccharide lysozyme inhibitor methyl 2-acetamido-3-deoxy-β-Dglucopyranoside. The binding modes of the two compounds to the enzyme in solution therefore appear to be analogous. Furthermore, a charge transfer interaction of the pyridinium: indole type is observed spectrophotometrically, indicating that the 2/lysozyme complex in solution is similar to that of the monosaccharide (and polysaccharide) inhibitor in crystals (proximity of the ligand O6 to the enzyme Trp62).