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• Świzdor, A
• Panek, A
• Milecka-Tronina, N
• Kołek, T
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• Świzdor, A
• Panek, A
• Milecka-Tronina, N
• Kołek, T
• [+] on PubMed
• Świzdor, A
• Panek, A
• Milecka-Tronina, N
• Kołek, T

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Int. J. Mol. Sci. 2012, 13(12), 16514-16543; doi:10.3390/ijms131216514

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Biotransformations Utilizing β-Oxidation Cycle Reactions in the Synthesis of Natural Compounds and Medicines

Alina Świzdor* , Anna Panek, Natalia Milecka-Tronina and Teresa Kołek

Department of Chemistry, Wroclaw University of Environmental and Life Sciences, Norwida 25, 50-375 Wroclaw, Poland

* Author to whom correspondence should be addressed.

Received: 31 August 2012; in revised form: 19 November 2012 / Accepted: 21 November 2012 / Published: 5 December 2012

(This article belongs to the Special Issue Organic Synthesis Using Biocatalyst)

Download PDF Full-Text [3412 KB, uploaded 5 December 2012 09:41 CET]

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.

Keywords: β-oxidation; biotransformation; bioconversion; sterol side-chain degradation; steroidal pharmaceuticals; flavoring lactones; L-carnitine; β-hydroxyisobutyric acid; vanilla flavor

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