Microbial arene oxidation

[1] The cis configuration of the product together with isotopic labeling studies implicate the intermediacy of dioxetanes.

[1] Aromatic esters are also good substrates for these enzymes, giving dihydrodiols in moderate yields along with some other oxidation products.

It catalyzes the oxidation of other polyclic aromatic compounds as well, although yields tend to be low for substrates other than naphthalene.

Oxidation takes place in an ipso-cis fashion, independent of the substitution pattern of the arene.

[1] An important limitation of the reaction is that only a single enantiomer of product is available when the wild type enzyme is used.

Enzymes that generate "unnatural" enantiomers must be engineered via site-directed mutagenesis or other biochemical techniques.

Because of concerns about the efficiency and selectivity of oxidation of more complex substrates, MAO is usually carried out early in synthetic sequences.