Abstract
β-Oxidation cycle reactions, which are key stages in the metabolism of fatty acids in eucaryotic cells and in processes with a significant role in the degradation of acids used by microbes as a carbon source, have also found application in biotransformations. One of the major advantages of biotransformations based on the β-oxidation cycle is the possibility to transform a substrate in a series of reactions catalyzed by a number of enzymes. It allows the use of sterols as a substrate base in the production of natural steroid compounds and their analogues. This route also leads to biologically active compounds of therapeutic significance. Transformations of natural substrates via β-oxidation are the core part of the synthetic routes of natural flavors used as food additives. Stereoselectivity of the enzymes catalyzing the stages of dehydrogenation and addition of a water molecule to the double bond also finds application in the synthesis of chiral biologically active compounds, including medicines. Recent advances in genetic, metabolic engineering, methods for the enhancement of bioprocess productivity and the selectivity of target reactions are also described.
Highlights
The literature continually brings to light a growing number of cases indicating that the stereochemical structure of a given compound determines its bioactivity, and that chirality is an important factor in drug efficacy [1,2]
Oxidative reactions of the β-oxidation cycle are preceded by activation of the fatty acid to its thioester with coenzyme A (CoA) catalyzed by ATP-dependent ligase (Figure 1, step 1)
This review mainly focuses on the application of the reaction of the β-oxidation cycle in biotransformation processes, some cases are not covered, e.g., the industrially most important example is the synthesis of polyhydroxyalkanoates and chiral 3-hydroxyacids
Summary
The literature continually brings to light a growing number of cases indicating that the stereochemical structure of a given compound determines its bioactivity (among others, its olfactory properties, activity as an insect pheromone), and that chirality is an important factor in drug efficacy [1,2] For these reasons, there is a vast range of research activity related to synthesis routes leading to the specific enantiomers of chiral biologically active compounds. Oxidative reactions of the β-oxidation cycle are preceded by activation of the fatty acid to its thioester with coenzyme A (CoA) catalyzed by ATP-dependent ligase (Figure 1, step 1). Mitochondrial β-oxidation is very efficient, usually converting R-CoA to the final product—acetyl-CoA This pathway constitutes the major process by which fatty acids are oxidized to generate energy. Process workflow methodologies are developed to reduce the toxicity of the product towards the biocatalyst
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