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Figure 1. The overall reaction of catechol 1,2-dioxygenase. Using a non-heme iron(III) complex, 1,2-CTD is able to oxidatively cleave catechol into cis,cis-muconic acid. More specifically, 1,2-CTD is an intradiol dioxygenase, a family of catechol dioxygenases that cleaves the bond between the phenolic hydroxyl groups of catechol using an Fe 3 ...
Catechol dioxygenases are metalloprotein enzymes that carry out the oxidative cleavage of catechols.This class of enzymes incorporate dioxygen into the substrate.Catechol dioxygenases belong to the class of oxidoreductases and have several different substrate specificities, including catechol 1,2-dioxygenase (EC 1.13.11.1), catechol 2,3-dioxygenase (EC 1.13.11.2), and protocatechuate 3,4 ...
Catechol (/ ˈ k æ t ɪ tʃ ɒ l / or / ˈ k æ t ɪ k ɒ l /), also known as pyrocatechol or 1,2-dihydroxybenzene, is an organic compound with the molecular formula C 6 H 4 (OH) 2. It is the ortho isomer of the three isomeric benzenediols. This colorless compound occurs naturally in trace amounts.
The catechol dioxygenases, some of the most well-studied dioxygenase enzymes, use dioxygen to cleave a carbon-carbon bond of an aromatic catechol ring system. [4] Catechol dioxygenases are further classified as being “extradiol” or “intradiol,” and this distinction is based on mechanistic differences in the reactions (figures 1 & 2).
There are three structural isomers: 1,2-dihydroxybenzene (the ortho isomer) is commonly known as catechol, 1,3-dihydroxybenzene (the meta isomer) is commonly known as resorcinol, and 1,4-dihydroxybenzene (the para isomer) is commonly known as hydroquinone. [1]
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The catalytic cycle begins with the catechol oxidase in its native oxidized Cu(II)-Cu(II) state with a coordinated hydroxide ion bridging the two copper centers. As catechol enters the active site, a proton is abstracted from one of the alcohols. The catechol coordinates with a Cu(II) center in a monodentate fashion, displacing one of the ...