Design of inhibitors of scytalone dehydratase: Probing interactions with an asparagine carboxamide

GS Basarab, DB Jordan, TC Gehret…

Index: Basarab, Gregory S.; Jordan, Douglas B.; Gehret, Troy C.; Schwartz, Rand S. Bioorganic and Medicinal Chemistry, 2002 , vol. 10, # 12 p. 4143 - 4154

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Citation Number: 13

Abstract

Among the active-site residues of scytalone dehydratase, the side-chain carboxamide of asparagine 131 has the greatest potential for strong electrostatic interactions. Structure- based inhibitor design aimed at enhancing interactions with this residue led to the synthesis of a series of highly potent inhibitors that have a five-or six-membered ring containing a carbonyl functionality for hydrogen bonding. To achieve a good orientation for hydrogen ...