Evidence for substantial intramolecular heterogeneity in the stable carbon isotopic composition of phytol in photoautotrophic organisms
van der Meer, Marcel T. J.
Hayes, John M.
Sinninghe Damste, Jaap S.
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KeywordPhytol; Phytane; Pristane; Stable carbon isotope; Mevalonic acid pathway; 2-C-methylerythritol-4-phosphate pathway; 2,6,10-trimethylpentadecan-2-one
The ubiquitous isoprenoid phytol was isolated from a range of algae, terrestrial plants and a bacterium and its two terminal carbon atoms were quantitatively removed by chemical oxidation. The product, 6,10,14-trimethylpentadecan-2-one, was depleted in 13C by 1-4‰ relative to the parent phytol. This difference is significant, and indicates that the pathway for biosynthesis of phytol induces substantial intramolecular stable carbon isotopic fractionations. The nature and magnitude of the fractionations suggest strongly that it is associated both with the biosynthesis of isopentenyl pyrophosphate via the 2-C-methylerythritol-4-phosphate pathway and with the formation of carotenoids and phytol from geranyl-geraniolphosphate. As a result of these large, intramolecular isotopic differences, diagenetic products formed by loss of C, such as pristane, may be naturally depleted in 13C by several permil relative to phytane.
Author Posting. © Elsevier B.V., 2007. This is the author's version of the work. It is posted here by permission of Elsevier B.V. for personal use, not for redistribution. The definitive version was published in Organic Geochemistry 39 (2008): 135-146, doi:10.1016/j.orggeochem.2007.09.002.
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