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

C Pasquarello; R Demange; P Vogel

doi:10.1016/s0960-894x(99)00064-5

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

Bioorg Med Chem Lett. 1999 Mar 8;9(5):793-6. doi: 10.1016/s0960-894x(99)00064-5.

Authors

C Pasquarello¹, R Demange, P Vogel

Affiliation

¹ Institut de chimie organique de l'Université de Lausanne, BCH, Lausanne-Dorigny, Switzerland.

PMID: 10201849
DOI: 10.1016/s0960-894x(99)00064-5

Abstract

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).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetylgalactosamine / analogs & derivatives
Acetylgalactosamine / pharmacology
Animals
Aspergillus / enzymology
Chickens
Enzyme Inhibitors / chemical synthesis*
Enzyme Inhibitors / pharmacology
Fabaceae / enzymology
Liver / enzymology
Mannose / chemical synthesis*
Mannose / pharmacology
Plants, Medicinal
Rhizopus / enzymology
beta-Galactosidase / antagonists & inhibitors*

Substances

Enzyme Inhibitors
beta-Galactosidase
Acetylgalactosamine
Mannose