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On the reaction mechanism of L-lactate oxidase : Quantitative structure-activity analysis of the reaction with para-substituted L-mandelates

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1997

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Yorita, Kazuko
Janko, Karl
Aki, Kenji
Ghisla, Sandro
Palfey, Bruce A.
Massey, Vincent

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Published

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Proceedings of the National Academy of Sciences : PNAS. 1997, 94(18), pp. 9590-9595. ISSN 0027-8424. eISSN 1091-6490

Zusammenfassung

The rate constants for reduction of the flavoenzyme, L-lactate oxidase, and a mutant (in which alanine 95 is replaced by glycine), by a series of para-substituted mandelates, in both the 2-1H- and 2-2H- forms, have been measured by rapid reaction spectrophotometry. In all cases, significant isotope effects (1H/2H = 3-7) on the rate constants of flavin reduction were found, indicating that flavin reduction is a direct measure of α-C-H bond breakage. The rate constants show only a small influence of the electronic characteristics of the substituents, but show a good correlation when combined with some substituent volume parameters. A surprisingly good correlation is found with the molecular mass of the substrate. The results are compatible with any mechanism in which there is little development of charge in the transition state. This could be a transfer of hydride to the flavin N(5) position or a synchronous mechanism in which the α-C-H is formally abstracted as a H+ while the resulting charge is simultaneously neutralized by another event.

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570 Biowissenschaften, Biologie

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ISO 690YORITA, Kazuko, Karl JANKO, Kenji AKI, Sandro GHISLA, Bruce A. PALFEY, Vincent MASSEY, 1997. On the reaction mechanism of L-lactate oxidase : Quantitative structure-activity analysis of the reaction with para-substituted L-mandelates. In: Proceedings of the National Academy of Sciences : PNAS. 1997, 94(18), pp. 9590-9595. ISSN 0027-8424. eISSN 1091-6490
BibTex
@article{Yorita1997react-8563,
  year={1997},
  title={On the reaction mechanism of L-lactate oxidase : Quantitative structure-activity analysis of the reaction with para-substituted L-mandelates},
  number={18},
  volume={94},
  issn={0027-8424},
  journal={Proceedings of the National Academy of Sciences : PNAS},
  pages={9590--9595},
  author={Yorita, Kazuko and Janko, Karl and Aki, Kenji and Ghisla, Sandro and Palfey, Bruce A. and Massey, Vincent}
}
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