Biosynthetic studies of marine lipids. 38. Mechanism ...

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Title Biosynthetic studies of marine lipids. 38. Mechanism and scope of sterol side chain dealkylation in sponges: evidence for concurrent alkylation and dealkylation
Author(s) Russell G. Kerr, S. L. Kerr, S. Malik, C. Djerassi
Journal Journal of the American Chemical Society
Date 1992
Volume 114
Issue 1
Start page 299
End page 303
Abstract A biosynthetic study has been performed to elucidate the precise mechanisms of sterol side chain dealkylation in marine sponges. This process resembles that of insects by involving the oxidation of common dietary sterols with unsaturation at C-24(28) (24-methylenecholesterol (8), fucosterol (3), and isofucosterol (4)) to their 24,28-epoxides (9 and 5). Loss of formaldehyde (or acetaldehyde) then produces desmosterol (6), which is subsequently reduced to cholesterol (7). The existence of this pathway in sponges is particularly surprising as these organisms are also capable of the reverse process: S-adenosylmethionine-mediated alkylation. The simultaneous operation of these competing processes was demonstrated using doubly labeled sterol precursors.

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