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 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.
Chevrier
Carine
C
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
D000606:Amino Sugars / Q000494:pharmacology*; D004791:Enzyme Inhibitors / Q000494:pharmacology*; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D009682:Magnetic Resonance Spectroscopy; D013780:Tetroses / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D000606:Amino Sugars; D004791:Enzyme Inhibitors; D013780:Tetroses; D006026:Glycoside Hydrolases; C073321:erythrose