Formation of Halogenated Medium Chain Hydrocarbons by a Lipoxygenase/Hydroperoxide Halolyase-Mediated Transformation in Planktonic Microalgae

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• 作者：Thomas Wichard and Georg Pohnert
• 刊名：Journal of the American Chemical Society
• 出版年：2006
• 出版时间：June 7, 2006
• 年：2006
• 卷：128
• 期：22
• 页码：7114 - 7115
• 全文大小：49K
• 年卷期：v.128,no.22(June 7, 2006)
• ISSN：1520-5126

文摘

A rapid transformation of eicosapentaenoic acid is initiated upon disintegration of cells of the marine diatom Stephanopyxis turris. In contrast to any other fatty acid cleaving activity known, this diatom releases a blend of chlorinated C8 hydrocarbons in addition to an unsaturated 12-oxo acid. Using labeled precursors, trapping experiments, and selective inhibition of enzyme activities, we were able to show that a lipoxygenase activates the C20 fatty acid to a hydroperoxide, which is subsequently cleaved by a new hydroperoxide halolyase to the C8 and C12 products. This adds a fundamentally new pathway to the limited set of halogenating enzymatic activities known from nature.