Journal of Organic Chemistry p. 4992 - 4997 (1988)
Update date:2022-08-04
Lesuisse, Dominique
Berchtold, Glenn A.
A synthesis of (-)- and (+/-)-(Z)-9-methylchorismic acid (3) is reported.The half-life for the uncatalyzed Claisen rearrangement of (+/-)-3 in H2O (pH 7.5, 30 deg C) is 5.7 h.Chorismate analogue (-)-3 was a modest substrate for chorismate mutase (chorismate mutase-prephenate dehydrogenase from E. coli): Km = 4.0 mM, kcat./kuncat. = 4.2*104.It was established that the enzyme-catalyzed Claisen rearrangement of (-)-3 proceeds through a chairlike transition state in similar fashion to the chorismate mutase catalyzed rearrangement of (-)-chorismic acid (1).
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