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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
Author(s) -
Chakraborty Biswarup,
Paine Tapan Kanti
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201206922
Subject(s) - dioxygenase , cleavage (geology) , chemistry , cleave , ring (chemistry) , stereochemistry , bond cleavage , aromatic amino acids , ligand (biochemistry) , amino acid , combinatorial chemistry , catalysis , organic chemistry , biochemistry , receptor , biology , enzyme , paleontology , fracture (geology)
Biomimetic aromatic ring cleavage: An iron(II)‐2‐aminophenolate complex (see picture, right) with a tetradentate ligand reacts with dioxygen to cleave the aromatic CC 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).