Inhibition of N-acetylglucosaminyltransfer enzymes : chemical-enzymatic synthesis of new five-membered acetamido azasugars

@article{Takaoka1993InhibitionON,
  title={Inhibition of N-acetylglucosaminyltransfer enzymes : chemical-enzymatic synthesis of new five-membered acetamido azasugars},
  author={Yoshikazu Takaoka and Tstsuya Kajimoto and Chi-Huey Wong},
  journal={Journal of Organic Chemistry},
  year={1993},
  volume={58},
  pages={4809-4812}
}
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… CONTINUE READING

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