engleski

Regioselective oxofunctionalization of steroids in deep eutectic solvents

Steroid production occupies a prominent place in the pharmaceutical industry, where steroids, after antibiotics, represent the second most important group of pharmaceutics. One of the major transformations in their synthesis path is oxofunctionalization, a regioselective introduction of oxygen into the gonane nucleus that can be catalysed by laccases. With the help of mediator systems, these enzymes can catalyse a wide range of organic substrates. Since most steroid compounds are not water- soluble, the use of deep eutectic solvents (DES) can overcome the disadvantages of common organic solvents. The aim of this research is to investigate the possible use of DES for Trametes versicolor laccase-mediated regioselective oxofunctionalization of 3β- hydroxyandrost-5-en-17-one to 3βhydroxyandrost-5- en-7, 17-dione, an important compound in medicine and pharmaceutics. The Conductor-like Screening Model for Real Solvents (COSMO-RS) was used to predict substrate solubility and to design a two-phase reaction system compatible with all reaction constituents. Three reaction parameters (substrate, mediator and enzyme concentration) were optimised by response surface methodology to obtain a high product yield. This research applies both empirical methods and mathematical models to find one solvent with optimal characteristics for this specific requirement.

deep eutectic solvents, steroids, oxofunctionalization

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