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

HB Wood, HP Buser, B Ganem

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

全文：HTML全文

被引用次数: 24

摘要

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 ...