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0344519795
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0 was determined by running the rearrangement reaction to completion (3 h) with wild-type BsCM at 2 mM chorismate and determining the isotope ratio on the mass spectrometer (experiment done in triplicate). The fractional conversion ∫ was determined by measuring the UV absorbance of the chorismate chromophore at 275 nm of the reaction mixture at the endpoint.
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0031360609
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An alternative two-step mechanism involving an ion pair intermediate cannot be ruled out with complete confidence. Such an ion pair could only be an intermediate if the partition ratio forward is small, however, which seems unlikely in light of the strongly exothermic nature of the reaction (Kast, P.; Tewari, Y. B.; Wiest, O.; Hilvert, D.; Houk, K. N.; Goldberg, R. N. J. Phys. Chem. B 1997, 101, 10976-10982).
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Normal hydrogen bonding probably has only a minor effect on the fractionation factor of an oxygen (the bond order is low), while full protonation has about a 2% effect (Knight, W. B., Weiss, P. M.; Cleland, W. W. J. Am. Chem. Soc. 1986, 108, 2759-2761 and references therein).
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0344519794
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7,20 the experimental isotope effects must be considered minimum values.
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