Synthesis and properties of a photoaffinity labeling reagent for protoporphyrinogen oxidases, the target enzymes of diphenyl ether herbicides.
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.
O'Connor
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N
Laboratoire de Chimie Organique Fondamentale et Appliquée, Faculté des Sciences, Angers, France.
Mornet
R
R
Matringe
M
M
Clair
D
D
Scalla
R
R
Fujimoto
T T
TT
Swithenbank
C
C
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
D000345:Affinity Labels; D006540:Herbicides; D007202:Indicators and Reagents; D010088:Oxidoreductases; D044925:Oxidoreductases Acting on CH-CH Group Donors; D050768:Protoporphyrinogen Oxidase