Y. Takaoka, T. Kajimoto, Chi‐Huey Wong
Aug 1, 1993
Citations
0
Influential Citations
58
Citations
Journal
Journal of Organic Chemistry
Abstract
Two new acetamido azasugars have been synthesized and tested as inhibitors of β-N-acetylglucosaminase. Ozonolysis of enantiomerically pure N-(4-phenyl-2-azido-3-butenyl)acetamide, derived from cinnamic aldehyde, followed by lipase-catalyzed resolution of the amine intermediate 5, gave 2-azido-3-acetamidopropanal which was then condensed with dihydroxyacetone phosphate by using FDP-aldolase. The condensed product was dephosphorylated and hydrogenated to afford the five-membered acetamido azasugar analogous to N-acetylglucosamine. Compounds 1 and 2 prepared in this manner were new competitive inhibitors of a β-N-acetylglucosaminidase with K i values of 1.9 and 3.6 μM, respectively, and could be useful for the synthesis of N-acetylglucosaminyltransferase inhibitors