Bioorganic & Medicinal Chemistry 2007-06-15

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

Index: Bioorg. Med. Chem. 15(12) , 4125-35, (2007)

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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.