NUCLEAR-MAGNETIC-RESONANCE CHARACTERIZATION OF 6-ALPHA-CHLORO-5-BETA-CHOLESTANE-3-BETA,5-DIOL FORMED FROM THE REACTION OF HYPOCHLOROUS ACIDWITH CHOLESTEROL

Hypochlorous acid generated by neutrophil myeloperoxidase has been sho wn to convert cholesterol into three different chlorohydrin isomers wh ich previously had not been fully characterized. We have reacted hypoc hlorous acid with cholesterol/1,2-dipalmitoyl phosphatidylcholine lipo somes to give these three major products and established that they are 6 beta-chloro-5 alpha-cholestane-3 beta,5-diol (chlorohydrin 1), 5 al pha-chloro-6 beta-cholestane-3 beta,6-diol (chlorohydrin 2) and 6 alph a-chloro-5 beta-cholestane-3 beta,5 -diol (chlorohydrin 3). These prod ucts were separated by thin-layer chromatography and fully characteriz ed by H-1, C-13, attached proton test, doublequantum correlation spect roscopy, total correlation spectroscopy, heteronuclear multiple bond c orrelation and heteronuclear multiple quantum coherence nuclear magnet ic resonance spectroscopy.