Abstract
Trihydroxy-2-thiaquinolizidines, a new class of bicyclic dideoxy-iminohexitol glycosidase inhibitor derivatives with nominally the d- gluco, l- ido, d- manno and l- gulo configurations were synthesized. X-ray analyses indicated that the preferred conformation for d- gluco and d- manno derivatives was a flat trans-fused system. Unlike deoxynojirimycin, the compound with d- gluco configuration was selective for α-glucosidases (yeast and rice) and showed no inhibitory activity towards β-glucosidase (almond), α-galactosidase (green coffee beans), α-galactosidase ( E. coli) and α-mannosidase (jack bean), while the l- ido derivative was specific for β-glucosidase (almond).
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