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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
Author(s) -
Verhoeven Jan,
Schwyzer Robert
Publication year - 1972
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19720550735
Subject(s) - chemistry , lysozyme , pyridinium , glycosidic bond , monosaccharide , stereochemistry , methyl iodide , iodide , chloride , ligand (biochemistry) , perchlorate , enzyme , medicinal chemistry , ion , organic chemistry , biochemistry , receptor
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‐ D glucopyranoside. 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 O 6 to the enzyme Trp 62 ).