The Mode of Action and the Structure of a Herbicide in Complex with its Target: Binding of Activated Hydantocidin to the Feedback Regulation Site of Adenylosuccinate Synthetase

The Mode of Action and the Structure of a Herbicide in Complex with its Target: Binding of Activated Hydantocidin to the Feedback Regulation Site of Adenylosuccinate Synthetase

(+)-Hydantocidin, a recently discovered natural spironucleoside with potent herbicidal activity, is shown to be a proherbicide that, after phosphorylation at the 5′ position, inhibits adenylosuccinate synthetase, an enzyme involved in de novo purine synthesis. The mode of binding of hydantocidin 5′-...

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Bibliographic Details
Published in:Proceedings of the National Academy of Sciences - PNAS Vol. 93; no. 18; pp. 9431 - 9436
Main Authors: Fonné-Pfister, R., Chemla, P., Ward, E., Girardet, M., Kreuz, K. E., Honzatko, R. B., Fromm, H. J., H.-P. Schär, Grütter, M. G., Cowan-Jacob, S. W.
Format: Journal Article
Language:English
Published: United States National Academy of Sciences of the United States of America 03-09-1996
National Acad Sciences
Subjects:
Adenylosuccinate Synthase - metabolism
Amino Acid Sequence
Atoms
Basil
Binding Sites
Biochemistry
Cell growth
Cells, Cultured
Crystallography, X-Ray
DNA, Complementary - analysis
Enzymes
Escherichia coli
Feedback
Herbicides
Herbicides - chemistry
Herbicides - metabolism
Hydantoins - chemistry
Hydantoins - metabolism
Inhibitory concentration 50
Molecular Sequence Data
Molecules
Phenotype
Plants
Protein Conformation
Sequence Homology, Amino Acid
Tetrahedrons
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Summary:(+)-Hydantocidin, a recently discovered natural spironucleoside with potent herbicidal activity, is shown to be a proherbicide that, after phosphorylation at the 5′ position, inhibits adenylosuccinate synthetase, an enzyme involved in de novo purine synthesis. The mode of binding of hydantocidin 5′-monophosphate to the target enzyme was analyzed by determining the crystal structure of the enzyme-inhibitor complex at 2.6- angstrom resolution. It was found that adenylosuccinate synthetase binds the phosphorylated compound in the same fashion as it does adenosine 5′-monophosphate, the natural feedback regulator of this enzyme. This work provides the first crystal structure of a herbicide-target complex reported to date.
Bibliography:ObjectType-Article-2
SourceType-Scholarly Journals-1
ObjectType-Feature-1
content type line 23
ISSN:0027-8424
1091-6490
DOI:10.1073/pnas.93.18.9431