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The Design and Synthesis of Inhibitors of Imidazoleglycerol Phosphate Dehydratase as Potential Herbicides

✍ Scribed by Cox, John M.; Hawkes, Timothy R.; Bellini, Peter; Ellis, Russell M.; Barrett, Roger; Swanborough, Joseph J.; Russell, Sally E.; Walker, Peter A.; Barnes, Nigel J.; Knee, Andrew J.; Lewis, Terence; Davies, Paul R.

Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
524 KB
Volume
50
Category
Article
ISSN
1526-498X

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✦ Synopsis

The discovery and exploration of a new class of broad-spectrum postemergent herbicides with a novel mode of action, namely the disruption of histidine biosynthesis via inhibition of imidazoleglycerol phosphate dehydratase (IGPD ; E.C. 4.2.1.19), are described. Clear structural similarities between the Ðrst member, produced during an attempt to produce analogues of glyphosate, and intermediates in histidine biosynthesis were noted. Several series of targets were designed, to mimic both the enzyme substrate and a putative reaction intermediate, and synthesised. Some examples were found to be both extremely potent inhibitors of the enzyme, having values as low as 0Γ‰3 nM, and phloem-mobile K i herbicides with levels of weed control similar to those shown by glyphosate. Further logical progress awaits a high-resolution X-ray structure determination of an enzyme-inhibitor complex.

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