Synthesis, glycosidase activity and X-ray crystallography of 3-amino-sugars

Abstract

The cleavage of two sugar epoxides, methyl 2,3-anhydro-α-D-mannopyranoside and 2,3-anhydro-α-D-allopyranoside, with amines is presented as a method for preparing a library of 3-amino-sugars (methyl 3-amino-3-deoxy-α-D-altropyranosides and methyl 3-amino-3-deoxy-α-D-glucopyranosides) as potential glycosidase inhibitors. Several of the altropyranosides were micromolar inhibitors of bovine liver β-galactosidase and almond β-glucosidase. X-Ray crystal structures were determined for one of the methyl 3-amino-3-deoxy-α-D-altropyranosides, 4t, and one of the methyl 3-amino-3-deoxy-α-D-glucopyranosides, 6d.