Synthesis of alpha-C(1 -> 3)-mannopyranoside of N-acetylgalactosamine, a new beta-galactosidase inhibitor

Pasquarello, C.Demange, R.Vogel, P.2005-11-092005-11-092005-11-09199910.1016/S0960-894X(99)00064-5https://infoscience.epfl.ch/handle/20.500.14299/219754Radical 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-ManpCH(2)(1-->3)-D-GalNAc, a C-disaccharide that inhibits beta-galactosidase from jack bean with IC50 = 9.4 mu M and K-i = 7.5 mu M (mixed mode of inhibition). (C) 1999 Elsevier Science Ltd. All rights reserved.carbohydrate mimeticsenzyme inhibitorsC-glycosidationC-disaccharidesoligosaccharidesglycosidesSynthesis of alpha-C(1 -> 3)-mannopyranoside of N-acetylgalactosamine, a new beta-galactosidase inhibitortext::journal::journal article::research article