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Issue 14, 2006
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Synthesis, glycosidase activity and X-ray crystallography of 3-amino-sugars

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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.

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

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Publication details

The article was received on 25 Apr 2006, accepted on 25 May 2006 and first published on 12 Jun 2006


Article type: Paper
DOI: 10.1039/B605916C
Citation: Org. Biomol. Chem., 2006,4, 2724-2732
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    Synthesis, glycosidase activity and X-ray crystallography of 3-amino-sugars

    V. L. Maxwell, E. L. Evinson, D. P. G. Emmerson and P. R. Jenkins, Org. Biomol. Chem., 2006, 4, 2724
    DOI: 10.1039/B605916C

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