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1 2004

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Reakcje hydroksylacji z udziałem dehydrogenez : zastosowanie w syntezie

Kołek T., Świzdor A., Szpineter A.

Wiadomości Chemiczne

2004

[Z] 58, 3-4

245--262

Although the majority of enzymatic hydroxylation reactions is catalysed by monooxygenases, dehydrogenases also play an important role in many reactions of this type. For example, dehydrogenases take part in hydroxylation of alifatic acids or nicotinic acid and its analogue. These reactions are important for degradation, biosynthesis and metabolism processes. Also, enzymic hydroxylation has been succesfully applied to the synthesis of L-carnitine, which is pharmacologically important compound. Another synthetic application involves enantioselective hydroxylation of isobutyric acid, where the proper catalyst species selection may lead to each enantiomer of the product selectively. Both enantiomers of b-hydroxyisobutyric acid are known as valuable chiral synthons for synthesis of many biologically active compounds, i.e. drugs, vitamins and others. The mechanism of alifatic compounds hydroxylation is well known - all the steps have been well documented. The reaction described were carried out by means of induced enzymes. The proof of dehydrogenases mediation in hydroxylation of N-heterocyclic substrates is the fact, that the oxygen in hydroxyl group derives from water, not from the air. Some of these reactions proceed quantitatively, affording very clean products. The reaction that found practical application of considerable importance is the hydroxylation of nicotinic acid (being precursor of a new generation insccticide) and its analogues. It is highly probable that the microbial hydroxylation of this type can find application in transformations of so called "enewable resource" (i.e. nicotine) in order to obtain important biologically active products.