The contribution of the substrate's carboxylate group to the mechanism of 4-oxalocrotonate tautomerase

H Lian, RM Czerwinski, TM Stanley, WH Johnson…

Index: Lian, Huiling; Czerwinski, Robert M.; Stanley, Thanuja M.; Johnson Jr., William H.; Watson, Robert J.; Whitman, Christian P. Bioorganic Chemistry, 1998 , vol. 26, # 3 p. 141 - 156

Full Text: HTML

Citation Number: 15

Abstract

4-Oxalocrotonate tautomerase (4-OT) converts 2-oxo-4E-hexenedioate (1) to 2-oxo-3E- hexenedioate (3) through the dienol intermediate, 2-hydroxy-2, 4-hexadiene-1, 6-dioate (2). Previous studies established that the isomerization of1to3is primarily a suprafacial process. It was also suggested that the 6-carboxylate group of the substrate maintains the regio-and stereochemical fidelity of the reaction by anchoring the substrate at the active site. A ...