Charge Transfer as a Molecular Probe in Systems of Biological Interest VI: Interactions between Lysozyme and the Methyl 2‐acetamido‐6‐O‐(N‐methyl‐isonicotinylium)‐2‐deoxy‐β‐D‐glucopyranoside Ion

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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).