Intradiol Aromatic Ring Cleavage in a Dioxygenase Model System
نویسنده
چکیده
Dennis G. Brown* and William J. Hughes Department of Chemistry, University of Idaho, Moscow, Idaho, USA 83843 Z. Naturforsch. 36b, 1324-1330 (1981); received March 23, 1981 Dioxygenase Model, Copper, Catechol The complex (3-n-nonylcatecholato)(l,10-phenanthroline)copper(II) reacts with molecular oxygen to give an isomeric mixture of 2-n-nonylmuconic acid and several secondary oxidation products. The catecholato ligand is oxidatively cleaved in an intradiol fashion reminescent of the reactions catalyzed by intradiol aromatic dioxygenases. The 1,10phenanthroline ligand can be quantitatively recovered and is not oxidized. In addition to characterization of oxidation products, the kinetics of oxygen consumption have been analyzed. The rate law for oxygen uptake is —d[C>2]/dt = k[02] [copper]2.
منابع مشابه
Copper(II) Complexes Containing 3-n-Nonylcatechol: Preparation and Ligand Oxidation
Copper, Dioxygenase, Urushiol Model, Catechol Ternary copper(II) complexes containing the dianion of 3-n-nonylcatechol and a number of bidentate nitrogen containing counter ligands have been prepared and characterized. It has been demonstrated that, in the presence of oxygen, the catecholato ligand undergoes intradiol ring cleavage in a fashion similar to that carried out by intradiol aromatic ...
متن کاملCatechol dioxygenases.
Catechol dioxygenases are key enzymes in the metabolism of aromatic rings by soil bacteria. Catechol dioxygenases have been found that participate in the metabolism of halogenated aromatic compounds and, in doing so, play a key role in bioremediation of halogenated pollutants. The catechol dioxygenases can be divided into two major groups: those that cleave the aromatic ring between the vicinal...
متن کاملRing-cleaving dioxygenases with a cupin fold.
Ring-cleaving dioxygenases catalyze key reactions in the aerobic microbial degradation of aromatic compounds. Many pathways converge to catecholic intermediates, which are subject to ortho or meta cleavage by intradiol or extradiol dioxygenases, respectively. However, a number of degradation pathways proceed via noncatecholic hydroxy-substituted aromatic carboxylic acids like gentisate, salicyl...
متن کاملExtradiol cleavage of 3-methylcatechol by catechol 1,2-dioxygenase from various microorganisms.
The isofunctional enzymes of catechol 1,2-dioxygenase from species of Acinetobacter, Pseudomonas, Nocardia, Alcaligenes, and Corynebacterium oxidize 3-methylcatechol according to both the intradiol and extradiol cleavage patterns. However, the enzyme preparations from Brevibacterium and Arthrobacter have only the intradiol cleavage activity. Comparison of substrate specificity among these isofu...
متن کاملMicrobes and the mechanism of degradation of organic pollutants
The microbial degradation of aromatic compounds has tremendous practical significance. Both aerobic and anaerobic microorganisms have been isolated that degrade aromatic compounds, but much more is known about aerobic pathways. In general, degradation proceeds in two phases. First, an aromatic compound is prepared for ring cleavage by a variety of ring modification reactions. Of the many divers...
متن کامل