Inhibition of 5-enolpyruvoylshikimate 3-phosphate (EPSP) synthase by analogs of the tetrahedral intermediate and of EPSP

…, CT Lauhon, R Nyfeler, A Faessler…

Index: Alberg, David G.; Lauhon, Charles T.; Nyfeler, Robert; Faessler, Alex; Bartlett, Paul A. Journal of the American Chemical Society, 1992 , vol. 114, # 9 p. 3535 - 3546

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Citation Number: 67

Abstract

Abstract: A number of analogues of the intermediate (1) and product of the enzyme EPSP synthase are described. Inert analogues that show high affinity for the enzyme from Petunia hybrida are produced by replacing the labile ketal phosphate moiety of this intermediate with a phosphonate (4) or by stabilizing the ketal phosphate against ionization through introduction of fluorine substituents (5 and 6). The most potent inhibitor is the R- ...