Molecular orbital calculations are used to determine structural and electronic characteristics of a series of sugar mimics, which are correlated with experimentally determined activity toward glycosidases. Differences in activity between α- and β-glycosidase correlate to the position of the HOMO surface of the neutral form of the inhibitor. A correlation is also found between relative activity and energy of the HOMO.
Keywords: Glycosidase inhibitors, Density functional theory, Natural charges, HOMO surface, Glucose, Nojirimycin, Aminocyclopentitols
Rights & PermissionsPrintExport