Carbohydrate Research p. 259 - 264 (1997)
Update date:2022-08-03
Topics:
Kameda, Yukihiko
Kawashima, Kanae
Takeuchi, Masayoshi
Ikeda, Kyoko
Asano, Naoki
Matsui, Katsuhiko
Manno- and galacto-validamines, which are epimers of validamine, were semi-synthesized by the configurational inversion of validamine, a pseudo-sugar analogue of α-D-glucopyranose that has inhibitory activity for α-glucosidases. The inhibitory activities of these analogues were determined against several mannosidases and galactosidases. Manno-validamine shows potent inhibition for the α-mannosidases (competitive, K(i) = 4.6 x 10-5 M for jack beans, and competitive, K(i) = 2.8 x 10-5 M for almonds), and galacto-validamine shows weak inhibition for the α-galactosidases (coffee bean and E. coli). The inhibitory effect of the epimers on the N-linked oligosaccharide-processing mannosidases involved in glycoprotein biosynthesis and lysosomal mannosidase from rat liver were also examined. Mannovalidamine shows potent inhibition on the endoplasmic reticulumal α-mannosidase (competitive, K(i) = 1.2 x 10-6 M), Golgi mannosidases IA, II (competitive, K(i) = 2.8 X 10-5 M), and lysosomal α-mannosidase (competitive, K(i) 1.7 x 10-5 M).
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