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J. Biol. Chem., Vol. 266, Issue 10, 6124-6132, 04, 1991
RT Fischer, JM Trzaskos, RL Magolda, SS Ko, CS Brosz and B Larsen
Conditions have been identified which permit metabolic formation of the
third oxidized intermediate in the lanosterol 14 alpha-methyl demethylase
reaction cascade. Metabolism of either the immediate precursor substrate 3
beta-hydroxylanost-8-en-32-al or lanost-8-ene-3 beta,32-diol under mixed
function oxidase conditions affords formation of the intermediate. It must
be emphasized that the intermediate can only be detected if saponification
procedures are omitted during sterol isolation. Comparative chemical and
biochemical studies of the isolated metabolite with 3 beta,15
alpha-dihydroxylanost-8-en-32-al reveal that the metabolite is not the 15
alpha-hydroxylanosterol aldehyde, a putative demethylase intermediate. The
metabolite is efficiently converted to the demethylated delta 8,14-diene
sterol in the absence of molecular oxygen or NADPH, thus supporting its
identity as the final oxidized intermediate in the lanosterol 14
alpha-methyl demethylase cascade. 1H NMR analysis shows a proton resonance
at 7.86 ppm consistent with a formyloxy proton. Mass spectral and infrared
analysis of the metabolite clearly establish oxygen insertion into the
immediate precursor substrate, 3 beta-hydroxylanost-8-en-32-al.
Collectively, the biochemical and chemical characteristics of the
metabolite support a structural assignment for the metabolite as 14
alpha-formyloxy-lanost-8- en-3 beta-ol.
Lanosterol 14 alpha-methyl demethylase. Isolation and characterization of the third metabolically generated oxidative demethylation intermediate [published erratum appears in J Biol Chem 1991 Jul 25;266(21):14137]
E.I. du Pont de Nemours Co., Inc., Medical Products Department, Wilmington, Delaware 19880-0400.
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