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?

摘要

Cyclic D- and L-4-aminothreose were synthesised from ethyl D- and L-tartrate, respectively. D-Aminothreose was a potent inhibitor of α-glucosidase and of α-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.