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?

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.

4-Amino-4-deoxy-d- and l-threose were synthesised from ethyl d- and l-tartrate, respectively, and evaluated against glycosidases. From these data as well as the inhibition potencies of other 4-amino-4-deoxy-tetroses, contribution of binding of each functionality of the 5 and 6- membered ring amino-sugars towards the various glycosidases is discussed.Figure optionsDownload as PowerPoint slide