Evidence for Hydrogen Abstraction from C1 of Taurine by the High-Spin Fe(IV) Intermediate Detected during Oxygen Activation by Taurine:α -Ketoglutarate Dioxygenase (TauD)

John C. Price; Eric W. Barr; Timothy E. Glass; Carsten Krebs; J. Martin Bollinger

doi:10.1021/ja037400h

Evidence for Hydrogen Abstraction from C1 of Taurine by the High-Spin Fe(IV) Intermediate Detected during Oxygen Activation by Taurine:α -Ketoglutarate Dioxygenase (TauD)

John C. Price, Eric W. Barr, Timothy E. Glass, Carsten Krebs, J. Martin Bollinger

Research output: Contribution to journal › Article › peer-review

339 Scopus citations

Abstract

The Fe(II)- and α-ketoglutarate-dependent dioxygenases catalyze hydroxylation reactions of considerable biomedical and environmental significance. Recently, the first oxidized iron intermediate in the reaction of a member of this family, taurine:α-ketoglutarate dioxygenase (TauD), was detected and shown to be a high-spin, formally Fe(IV) complex. The demonstration in this study that decay of the Fe(IV) complex is ∼30-fold slower when it is formed in the presence of 1-[²H]₂-taurine provides evidence that the intermediate abstracts hydrogen from C1, the site of hydroxylation, and suggests that quantum-mechanical tunneling may contribute to C1-H cleavage.

Original language	English (US)
Pages (from-to)	13008-13009
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	125
Issue number	43
DOIs	https://doi.org/10.1021/ja037400h
State	Published - Oct 29 2003

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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title = "Evidence for Hydrogen Abstraction from C1 of Taurine by the High-Spin Fe(IV) Intermediate Detected during Oxygen Activation by Taurine:α -Ketoglutarate Dioxygenase (TauD)",

abstract = "The Fe(II)- and α-ketoglutarate-dependent dioxygenases catalyze hydroxylation reactions of considerable biomedical and environmental significance. Recently, the first oxidized iron intermediate in the reaction of a member of this family, taurine:α-ketoglutarate dioxygenase (TauD), was detected and shown to be a high-spin, formally Fe(IV) complex. The demonstration in this study that decay of the Fe(IV) complex is ∼30-fold slower when it is formed in the presence of 1-[2H]2-taurine provides evidence that the intermediate abstracts hydrogen from C1, the site of hydroxylation, and suggests that quantum-mechanical tunneling may contribute to C1-H cleavage.",

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Evidence for Hydrogen Abstraction from C1 of Taurine by the High-Spin Fe(IV) Intermediate Detected during Oxygen Activation by Taurine:α -Ketoglutarate Dioxygenase (TauD). / Price, John C.; Barr, Eric W.; Glass, Timothy E. et al.
In: Journal of the American Chemical Society, Vol. 125, No. 43, 29.10.2003, p. 13008-13009.

Research output: Contribution to journal › Article › peer-review

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AU - Price, John C.

AU - Barr, Eric W.

AU - Glass, Timothy E.

AU - Krebs, Carsten

AU - Bollinger, J. Martin

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AB - The Fe(II)- and α-ketoglutarate-dependent dioxygenases catalyze hydroxylation reactions of considerable biomedical and environmental significance. Recently, the first oxidized iron intermediate in the reaction of a member of this family, taurine:α-ketoglutarate dioxygenase (TauD), was detected and shown to be a high-spin, formally Fe(IV) complex. The demonstration in this study that decay of the Fe(IV) complex is ∼30-fold slower when it is formed in the presence of 1-[2H]2-taurine provides evidence that the intermediate abstracts hydrogen from C1, the site of hydroxylation, and suggests that quantum-mechanical tunneling may contribute to C1-H cleavage.

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Evidence for Hydrogen Abstraction from C1 of Taurine by the High-Spin Fe(IV) Intermediate Detected during Oxygen Activation by Taurine:α -Ketoglutarate Dioxygenase (TauD)

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