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 [14C]-cholestane-3β,5α,6β-triol and [14C]-6-oxo-cholestan-3β,5α-diol. In the present study we report the one-step synthesis of [14C]-cholestane-3β,5α,6β-triol and [14C]-6-oxo-cholestan-3β,5α-diol by oxidation of [14C]-cholesterol with iodide metaperiodate (HIO4).