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- W1973478031 abstract "A 12-step route is presented starting from 1,2:5,6-di-O-isopropylidene-α-d-glucofuranose for the preparation of the title compounds and their l-altro analogues. Their synthesis is based on the reduction with Raney nickel of a protected 5-hydroxyimino derivative of l-arabino-hexofuranos-5-ulose, with the following improvements for the preparation of a d-galactofuranose derivative: oxidation at C-3 with pyridinium dichromate-acetic anhydride, stereospecific reduction of a 3-O-acetyl-hex-3-enofuranose intermediate to the d-gulo derivative, and inversion at C-3 of its 3-tosylate with tetrabutylammonium acetate in chlorobenzene. α-d-Galactosidase from coffee beans and from Escherichia coli and β-d-galactosidase from E. coli and Aspergillus wentii were inhibited with Ki values that ranged from 0.0007 to 8.0μm. Formation of the enzyme-inhibitor complexes with the d-galactose analogue was on the time-scale of minutes, whereas the d-galactitol analogue showed a slow approach to the inhibition only with α-d-galactosidase from coffee beans and β-d-galactosidase from A. wentii. N-Alkylation of the d-galactitol analogue was detrimental to the inhibition except for β-d-galactosidase from E. coli and β-d-glucosidase from almonds, but, even with these enzymes, the observed affinity enhancements were 102 to 103-times smaller than those of N-alkylated d-galactosylamine and d-glucosylamine." @default.
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- W1973478031 date "1986-11-01" @default.
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- W1973478031 title "Synthesis of 5-amino-5-deoxy-d-galactopyranose and 1,5-dideoxy-1,5-imino-d-galactitol, and their inhibition of α- and β-d-galactosidases" @default.
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- W1973478031 doi "https://doi.org/10.1016/s0008-6215(00)90138-1" @default.
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