Trihydroxy-2-thiaquinolizidine derivatives as a new class of bicyclic glycosidase inhibitors |
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Authors: | Li Gao |
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Institution: | Department of Chemistry, Michigan State University, East Lansing, MI 48824, USA |
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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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Keywords: | Glycosidase inhibitors Aza-sugars Iminoalditols Glucosidases Mannosidases Enzymology Drugs |
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