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Aromatic Ring Cleavage of 2-Amino-4-tert-butylphenol by a Nonheme Iron(II) Complex: Functional Model of 2-Aminophenol Dioxygenases

Authors

  • Biswarup Chakraborty,

    1. Department of Inorganic Chemistry, Indian Association for the Cultivation of Science, 2A & 2B Raja S. C. Mullick Road, Jadavpur, Kolkata-700032 (India)
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  • Dr. Tapan Kanti Paine

    Corresponding author
    1. Department of Inorganic Chemistry, Indian Association for the Cultivation of Science, 2A & 2B Raja S. C. Mullick Road, Jadavpur, Kolkata-700032 (India)
    • Department of Inorganic Chemistry, Indian Association for the Cultivation of Science, 2A & 2B Raja S. C. Mullick Road, Jadavpur, Kolkata-700032 (India)
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  • T.K.P. acknowledges the DST, Government of India (Project SR/S1/IC-51/2010) for financial support. B.C. thanks CSIR, India, for a fellowship. The crystal-structure determination was performed at the DST-funded National Single Crystal Diffractometer Facility in the Department of Inorganic Chemistry, IACS.

Abstract

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Biomimetic aromatic ring cleavage: An iron(II)-2-aminophenolate complex (see picture, right) with a tetradentate ligand reacts with dioxygen to cleave the aromatic C[BOND]C bond of 2-amino-4-tert-butylphenolate to form 4-tert-butyl-2-picolinate. This complex represents a functional model of 2-aminophenol-1,6-dioxygenase (APD) and 3-hydroxyanthranilate-3,4-dioxygenase (HAD).

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