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

Abstract : 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).
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https://www.hal.inserm.fr/inserm-00968933
Contributor : Marc Poirot <>
Submitted on : Tuesday, April 1, 2014 - 6:47:00 PM
Last modification on : Tuesday, June 30, 2020 - 3:10:55 AM

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Maud Voisin, Sandrine Silvente-Poirot, Marc Poirot. One step synthesis of 6-oxo-cholestan-3β,5α-diol.. Biochemical and Biophysical Research Communications, Elsevier, 2014, epub ahead of print. ⟨10.1016/j.bbrc.2014.01.138⟩. ⟨inserm-00968933⟩

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