Epoxidation of 6,7- and 10,11-oxidosqualenes by the squalene epoxidase present in rat liver microsomes |
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Authors: | Jos-Luis Abad Josefina Casas Joaquín Abin Angel Messeguer |
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Institution: | a Dpt. of Biological Organic Chemistry CID (CSIC). J. Girona, 18. 08034 Barcelona, Spain b Dpt. of Neurochemistry. CID (CSIC). J. Girona, 18. 08034 Barcelona, Spain |
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Abstract: | Incubation of 6,7-oxidosqualene (2) or 10,11-oxidosqualene (3) with rat liver microsomes led to the formation of mixtures of the corresponding dioxidosqualenes (4 and 5, or 6 and 7, respectively), resulting from the epoxidation of 2 and 3 at their terminal double bonds. The epoxidation requires the presence of both NADPH and FAD. In addition, the HPLC analysis of the Mosher esters resulting from the controlled hydrolysis of dioxide 5 to give the corresponding epoxydiols 9 followed by derivatization with (R)-MTPA, showed that the epoxidation had been stereoselective. These facts support the hypothesis that these dioxidosqualenes had been generated by the squalene epoxidase present in the incubation medium. |
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Keywords: | dioxidosqualene oxidosqualene squalene epoxidase (EC 1 14 99 7) epoxidation |
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