Synthesis and evaluation of amino-threoses in D- and L-series: are five membered ring amino-sugars more potent glycosidase inhibitors than the six membered ones?

Carine Chevrier; Albert Defoin; Céline Tarnus

doi:10.1016/j.bmc.2007.03.073

Synthesis and evaluation of amino-threoses in D- and L-series: are five membered ring amino-sugars more potent glycosidase inhibitors than the six membered ones?

Bioorg Med Chem. 2007 Jun 15;15(12):4125-35. doi: 10.1016/j.bmc.2007.03.073. Epub 2007 Mar 30.

Authors

Carine Chevrier¹, 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: 17434740
DOI: 10.1016/j.bmc.2007.03.073

Abstract

Cyclic D- and L-4-aminothreose were synthesised from ethyl D- and L-tartrate, respectively. D-aminothreose was a potent inhibitor of alpha-glucosidase and of alpha-mannosidase. From the glycosidase inhibition potencies of the four 4-amino-4-deoxy-tetroses, the contribution of binding of each functionality of the 5 and 6 membered ring amino-sugars towards the various glycosidases is discussed.

Publication types

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

MeSH terms

Amino Sugars / pharmacology*
Enzyme Inhibitors / pharmacology*
Glycoside Hydrolases / antagonists & inhibitors*
Magnetic Resonance Spectroscopy
Tetroses / chemical synthesis*
Tetroses / chemistry
Tetroses / pharmacology*

Substances

Amino Sugars
Enzyme Inhibitors
Tetroses
Glycoside Hydrolases
erythrose