Phosphonate analogs of chorismic acid: synthesis and evaluation as mechanism-based inactivators of chorismate mutase

HB Wood, HP Buser, B Ganem

Index: Wood, Harold B.; Buser, Hans-Peter; Ganem, Bruce Journal of Organic Chemistry, 1992 , vol. 57, # 1 p. 178 - 184

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Citation Number: 24

Abstract

The mechanism of chorismate mutase, the enzyme which catalyzes the Claisen arrangement of chorismic to prephenic acid, remains a fascinating area for bioorganic research. This paper describes the enantioselective synthesis of phosphonochorismic acids 3 and 4, two potential mechanism-based mutase inactivators, utilizing new transition-metal- catalyzed insertion reactions of tetraalkyl diazophosphonates. Models establish that such ...