ISSN:
1434-193X
Keywords:
Carbohydrates
;
Aza sugars
;
Double reductive amination
;
Enzyme inhibitors
;
Glycosidase inhibitors
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
-The syntheses of azaMan-β-(1→6)-C-Glc (4), azaGlc-β-(1→6)-C-Glc (5), and azaGal-β-(1→6)-C-Glc (6) based upon double reductive amination of acetylenic carbohydrate-derived diketones is described. The required diketones are obtained by addition of the acetylenic sugar anion derived from dibromoolefin 7 to benzyl-protected mannopyranolactone, glucopyranolactone, or galactopyranolactone, followed by reduction of the ketose and oxidation of the resulting diol. Ensuing double reductive amination and hydrogenolysis affords the target compounds in reasonable to good yields. Enzyme inhibition tests show that neither of the three compounds 4, 5, and 6 inhibit β-glycosidases, while moderate to good inhibitory activities were found on α-glycosidases, the most active being 6 (α-galactosidase: Ki = 0.092 μM).
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
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