rapid assembly of a library of lipophilic iminosugars via the thiol–ene reaction yields promising pharmacological chaperones for the treatment of Gaucher disease

ED Goddard-Borger, MB Tropak…

Index: Goddard-Borger, Ethan D.; Tropak, Michael B.; Yonekawa, Sayuri; Tysoe, Christina; Mahuran, Don J.; Withers, Stephen G. Journal of Medicinal Chemistry, 2012 , vol. 55, # 6 p. 2737 - 2745

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Citation Number: 49

Abstract

A highly divergent route to lipophilic iminosugars that utilizes the thiol–ene reaction was developed to enable the rapid synthesis of a collection of 16 dideoxyiminoxylitols bearing various different lipophilic substituents. Enzyme kinetic analyses revealed that a number of these products are potent, low-nanomolar inhibitors of human glucocerebrosidase that stabilize the enzyme to thermal denaturation by up to 20 K. Cell based assays conducted ...

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