Synthesis of alpha-C(1-->3)-mannopyranoside of N-acetylgalactosamine, a new beta-galactosidase inhibitor.
Radical C-glycosidation of a 3-methylidene-7-oxabicyclo[2.2.1]heptan-2-one derivative with acetobromomannose gave a alpha-C-mannopyranoside that was converted into alpha-D-ManpCH2(1-->3)-D-GalNAc, a C-disaccharide that inhibits beta-galactosidase from jack bean with IC50 = 9.4 microM and Ki = 7.5 microM (mixed mode of inhibition).
Pasquarello
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C
Institut de chimie organique de l'Université de Lausanne, BCH, Lausanne-Dorigny, Switzerland.
Demange
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Vogel
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P
D000116:Acetylgalactosamine / Q000031:analogs & derivatives / Q000494:pharmacology; D000818:Animals; D001230:Aspergillus / Q000201:enzymology; D002645:Chickens; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D007887:Fabaceae / Q000201:enzymology; D008099:Liver / Q000201:enzymology; D008358:Mannose / Q000138:chemical synthesis* / Q000494:pharmacology; D010946:Plants, Medicinal; D012233:Rhizopus / Q000201:enzymology; D001616:beta-Galactosidase / Q000037:antagonists & inhibitors*
D004791:Enzyme Inhibitors; D001616:beta-Galactosidase; D000116:Acetylgalactosamine; D008358:Mannose