Cholesterol chlorohydrin

The formation of cholesterol chlorohydrins has been a subject of intense research [99-102]. The role of these compounds is not yet fully understood, but in addition to cytotoxicity and a possible action on atherosclerosis [100], they have been suggested to be biomarkers of myeloperoxidase-derived HOC1 [103]. Moreover, chlorohydrins and other halohydrins are useful intermediates for the synthesis of a vast range of biologically active natural and synthetic products [104, 105], In fact, considering the importance of these compounds, their preparation is of major interest. 

Heinecke JW, Li W, Mueller DM, Bohrer A, Turk J (1994) Cholesterol Chlorohydrin Synthesis by the Myeloperoxidase-Hydrogen Peroxide-Chloride System Potential Markers for Lipoproteins Oxidatively Damaged by Phagocytes. Biochemistry 33 10127... 

Heinecke, J. W., W. Li, D. M. Mueller, A. Bohrer, and J. Turk. 1994. Cholesterol chlorohydrin synthesis by the myeloperoxidase-hydrogen peroxide-chloride system Potential markers for lipoproteins oxidatively damaged by phagocytes. 33(33) 10127-36. 

Treatment of the chlorohydrin (328), obtained from cholesterol 5a,6a-epoxide (327), with potassium bisulphate followed by acetylation furnished the rearranged... 

Human white cells produce an enzyme called myeloperoxidase. This enzyme catalyzes the reaction between hydrogen peroxide and chloride ion to produce hypochlorous acid, HOCl, which reacts as if it were Cl OH. When attacked by white cells, cholesterol gives a chlorohydrin as the major product. 

---