Synthesis of halo enol lactones. Mechanism-based inactivators of serine proteases

GA Krafft, JA Katzenellenbogen

Index: Krafft,G.A.; Katzenellenbogen,J.A. Journal of the American Chemical Society, 1981 , vol. 103, p. 5459

Full Text: HTML

Citation Number: 126

Abstract

Abstract: Enol lactones bearing a halogen at the vinylic position are potential mechanism- based inactivators (suicide inactivators) of serine hydrolases, since acyl transfer to the active- site serine releases an a-halo ketone that can react with nucleophilic sites in the active-site region. Efficient syntheses of such halo enol lactones needed for enzymatic studies are described. 5-Hexynoic acids can be cyclized with mercuric ion catalysis to y-methylene ...