Asymmetric synthesis of the L-fuco-nojirimycin, a nanomolar alpha-L-fucosidase inhibitor

Mathieu Dubernet; Albert Defoin; Céline Tarnus

doi:10.1016/j.bmcl.2005.11.100

Asymmetric synthesis of the L-fuco-nojirimycin, a nanomolar alpha-L-fucosidase inhibitor

Bioorg Med Chem Lett. 2006 Mar 1;16(5):1172-4. doi: 10.1016/j.bmcl.2005.11.100. Epub 2005 Dec 20.

Authors

Mathieu Dubernet¹, Albert Defoin, Céline Tarnus

Affiliation

¹ Laboratoire de Chimie Organique et Bioorganique, UMR 7015, Ecole Nationale Supérieure de Chimie de Mulhouse, Université de Haute-Alsace, 3, rue Alfred Werner, F-68093 Mulhouse Cédex, France.

PMID: 16376079
DOI: 10.1016/j.bmcl.2005.11.100

Abstract

We describe the asymmetric synthesis of the 5-amino-5-deoxy-l-fucose (l-fuco-nojirimycin) which appears as a very potent fucosidase inhibitor with a K(i) value of 1 nM.

Publication types

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

MeSH terms

1-Deoxynojirimycin / analogs & derivatives
Animals
Cattle
Enzyme Inhibitors / chemical synthesis*
Enzyme Inhibitors / chemistry
Enzyme Inhibitors / pharmacology*
Glucosamine / analogs & derivatives*
Glucosamine / chemical synthesis
Glucosamine / chemistry
Glucosamine / pharmacology
Kidney / drug effects
Kidney / enzymology
Molecular Structure
Stereoisomerism
alpha-L-Fucosidase / antagonists & inhibitors*
alpha-L-Fucosidase / metabolism

Substances

Enzyme Inhibitors
fuconojirimycin
1-Deoxynojirimycin
alpha-L-Fucosidase
Glucosamine