Mechanism and stereospecificity of alpha-hydroxylation of lignoceric acid in rat brain. |
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Authors: | K Tatsumi S Murad Y Kishimoto |
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Affiliation: | 1. Eunice Kennedy Shriver Center for Mental Retardation at Walter E. Fernald State School, Waltham, Massachusetts 02154 USA;2. Department of Neurology, Massachusetts General Hospital, Boston, Massachusetts 02114 USA |
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Abstract: | Cerebronic acid (2-hydroxytetracosanoic acid) is the major fatty acid component of cerebrosides and sulfatides in mammalian brain. Our previous communication demonstrated the synthesis of cerebronic acid from lignoceric acid (tetracosanoic acid) by a rat brain preparation in the presence of molecular oxygen and a reduced pyridine nucleotide (Hoshi, M., and Kishimoto, Y. (1973) J. Biol. Chem., 248, 4123–4130). The present'studies on the conversion of (RS)-[2-3H]-, (RS)-[3-3H]-, (R)-[2-3H]-, and (S)-[2-3H]lignoceric acids to cerebronic acid by rat brain preparations establish that the pro-R hydrogen at the α-carbon of lignoceric acid is replaced by a hydroxyl group with overall retention of configuration. |
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Keywords: | To whom reprint requests should be addressed. |
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