One step synthesis of 6-oxo-cholestan-3β,5α-diol.

Cholesterol metabolism has been recently linked to cancer, highlighting the importance of the characterization of new metabolic pathways in the sterol series. One of these pathways is centered on cholesterol-5,6-epoxides (5,6-ECs). 5,6-ECs can either generate dendrogenin A, a tumor suppressor present in healthy mammalian tissues, or the carcinogenic cholestane-3β,5α,6β-triol (CT) and its putative metabolite 6-oxo-cholestan-3β,5α-diol (OCDO) in tumor cells. We are currently investigating the identification of the enzyme involved in OCDO biosynthesis, which would be highly facilitated by the use of commercially unavailable [(14)C]-cholestane-3β,5α,6β-triol and [(14)C]-6-oxo-cholestan-3β,5α-diol. In the present study we report the one-step synthesis of [(14)C]-cholestane-3β,5α,6β-triol and [(14)C]-6-oxo-cholestan-3β,5α-diol by oxidation of [(14)C]-cholesterol with iodide metaperiodate (HIO4).