Journal of Organic Chemistry p. 4809 - 4812 (1993)
Update date:2022-08-04
Topics:
Takaoka, Yoshikazu
Kajimoto, Tetsuya
Wong, Chi-Huey
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 dephospharylated 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 Ki values of 1.9 and 3.6 μM, respectively, and could be useful for the synthesis of N-acetylglucosaminyltransferase inhibitors.
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Doi:10.1002/jps.2600560732
(1967)Doi:10.1021/om400945d
(2014)Doi:10.1016/S0040-4039(00)74090-1
(1993)Doi:10.1016/S0040-4020(01)81880-9
(1993)Doi:10.1021/np400668k
(2014)Doi:10.1016/j.tetlet.2013.12.081
(2014)