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Bioorg Med Chem Lett. 2005 Jun 15;15(12):3071-5.

Total asymmetric synthesis of (-)-conduramine B-1 and of its enantiomer. N-Benzyl derivatives of conduramine B-1 are beta-glucosidase inhibitors.

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  • 1Laboratoire de Glycochimie et de Synthèse Asymétrique, Ecole Polytechnique Fédérale de Lausanne (EPFL), ISIC, BCH, CH-1015 Lausanne-Dorigny, Switzerland.

Abstract

The 'naked sugars' (+)- and (-)-7-oxabicyclo[2.2.1]hept-5-en-2-one have been converted into (-)-conduramine B-1 ((-)-3) and its enantiomer (+)-3, respectively. They have been condensed with a variety of aldehydes in the presence of NaBH(OAc)(3). The N-substituted derivatives 4 and ent-4 so-obtained have been tested against two alpha-glucosidases, two amyloglucosidases, two beta-glucosidases and one beta-xylosidase for their inhibitory activities. Although (-)-3 and (+)-3 do not inhibit any of these enzymes at 1mM concentration, N-benzylated derivatives of (-)-conduramine B-1 are selective and competitive inhibitors of beta-glucosidases with K(i) in low micromolecular range.

PMID:
15878273
[PubMed - indexed for MEDLINE]
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