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Stereochemistry of cholesterol hydroxylation at C-22 during pregnenolone biosynthesis
Authors:Carmenza Duque  Masuo Morisaki  Nobuo Ikekawa  Mikio Shikita
Institution:Laboratory of Chemistry for Natural Products, Tokyo Institute of Technology, Nagatsuta, Midori-ku, Yokohama 227, Japan;National Institute of Radiological Sciences, Anagawa, Chiba-shi 280, Japan
Abstract:Cholesterol and 20-hydroxycholesterol labelled at C-22 stereospecifically by deuterium were incubated with the enzyme of bovine adrenocortical mitochondria. The results indicated that hydroxylation occurs with retention of the configuration of C-22 to give exclusively the 22R stereoisomers of 22-hydroxy- and/or 20,22-dihydroxycholesterol.
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