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Synthesis and properties of a photoaffinity labeling reagent for protoporphyrinogen oxidases, the target enzymes of diphenyl ether herbicides. 1994
N O'Connor, and
R Mornet, and
M Matringe, and
D Clair, and
R Scalla, and
T T Fujimoto, and
C Swithenbank
Laboratoire de Chimie Organique Fondamentale et Appliquée, Faculté des Sciences, Angers, France.
A diazoketone 3 has been synthesized in two steps from acifluorfen 1, a diphenyl ether herbicide. Like the parent compound 1, the diazoketone 3 is toxic to plant cells and inhibits protoporphyrinogen oxidase, the molecular target of diphenyl ether herbicides. On photolysis of 3 in methanol, the generated carbene mainly undergoes the Wolff rearrangement to a ketene which further adds methanol, but many other products are observed. A tritiated derivative of 3 has been prepared which is suitable for photoaffinity labeling experiments.
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