Isochorismate pyruvate lyase: Difference between revisions
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==Chemistry== | ==Chemistry== | ||
The transformation of isochorismate to prephenate is a pericyclic reaction. IPL catalyzes the elimination of the enolpyruvyl side chain from isochorismate to give salicylate and pyruvate. This type of aromatization reaction is generally formulated as a baseinitiated process, but a dissociative mechanism involving initial cleavage of the C-O bond to give an ion pair intermediate is conceivable. A concerted pericyclic pathway, in which the hydrogen atom at C2 is transferred to C9 of the side chain simultaneous with C-O cleavage, which represents a third possibility, has been proposed as well. | The transformation of isochorismate to prephenate is a pericyclic reaction. IPL catalyzes the elimination of the enolpyruvyl side chain from isochorismate to give salicylate and pyruvate. This type of aromatization reaction is generally formulated as a baseinitiated process, but a dissociative mechanism involving initial cleavage of the C-O bond to give an ion pair intermediate is conceivable. A concerted pericyclic pathway [http://en.wikipedia.org/wiki/Pericyclic_reaction link title], in which the hydrogen atom at C2 is transferred to C9 of the side chain simultaneous with C-O cleavage, which represents a third possibility, has been proposed as well. | ||
The reaction is a one step mechanism (J. AM. CHEM. SOC. 2005, 127, 15002-15003). | The reaction is a one step mechanism (J. AM. CHEM. SOC. 2005, 127, 15002-15003). | ||