Asymmetric synthesis of the L-fuco-nojirimycin, a nanomolar alpha-L-fucosidase inhibitor.
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.
Dubernet
Mathieu
M
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.
Defoin
Albert
A
Tarnus
Céline
C
D017485:1-Deoxynojirimycin / Q000031:analogs & derivatives; D000818:Animals; D002417:Cattle; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D007668:Kidney / Q000187:drug effects / Q000201:enzymology; D015394:Molecular Structure; D013237:Stereoisomerism; D005644:alpha-L-Fucosidase / Q000037:antagonists & inhibitors* / Q000378:metabolism
D004791:Enzyme Inhibitors; C483525:fuconojirimycin; D017485:1-Deoxynojirimycin; D005644:alpha-L-Fucosidase; D005944:Glucosamine