title: Synthesis and properties of a photoaffinity labeling reagent for protoporphyrinogen oxidases, the target enzymes of diphenyl ether herbicides.
abstract: 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.
authors.affiliation: Laboratoire de Chimie Organique Fondamentale et Appliquée, Faculté des Sciences, Angers, France.
authors.forename: N
authors.initials: N
authors.lastname: O'Connor
authors.forename: R
authors.initials: R
authors.lastname: Mornet
authors.forename: M
authors.initials: M
authors.lastname: Matringe
authors.forename: D
authors.initials: D
authors.lastname: Clair
authors.forename: R
authors.initials: R
authors.lastname: Scalla
authors.forename: T T
authors.initials: TT
authors.lastname: Fujimoto
authors.forename: C
authors.initials: C
authors.lastname: Swithenbank
mesh_terms: D000345:Affinity Labels / Q000138:chemical synthesis* / Q000737:chemistry; D006540:Herbicides / Q000494:pharmacology*; D007202:Indicators and Reagents; D015394:Molecular Structure; D010088:Oxidoreductases / Q000037:antagonists & inhibitors*; D044925:Oxidoreductases Acting on CH-CH Group Donors; D010782:Photolysis; D050768:Protoporphyrinogen Oxidase; D013025:Glycine max / Q000187:drug effects / Q000201:enzymology / Q000254:growth & development
chemical_list: D000345:Affinity Labels; D006540:Herbicides; D007202:Indicators and Reagents; D010088:Oxidoreductases; D044925:Oxidoreductases Acting on CH-CH Group Donors; D050768:Protoporphyrinogen Oxidase