Curtin University Homepage
  • Library
  • Help
    • Admin

    espace - Curtin’s institutional repository

    JavaScript is disabled for your browser. Some features of this site may not work without it.
    View Item 
    • espace Home
    • espace
    • Curtin Research Publications
    • View Item
    • espace Home
    • espace
    • Curtin Research Publications
    • View Item

    Biosynthetic origin of the saw-toothed profile in d13C and d2Y of n-alkanes and systematic isotopic differences between n-, iso- and anteiso-alkanes in leaf waxes of land plants

    Access Status
    Fulltext not available
    Authors
    Zhou, Y.
    Grice, Kliti
    Stuart-Williams, H.
    Farquhar, G.
    Hocart, C.
    Lu, H.
    Liu, W.
    Date
    2010
    Type
    Journal Article
    
    Metadata
    Show full item record
    Citation
    Zhou, Youping and Grice, Kliti and Stuart-Williams, Hilary and Farquhar, Graham and, Hocart, Charles and Lu, Hong and Lui, Weiguo. 2010. Biosynthetic origin of the saw-toothed profile in δ13C and δ2Η of n-alkanes and systematic isotopic differences between n-, iso- and anteiso-alkanes in leaf waxes of land plants. Phytochemistry. 71 (4): pp.388-403.
    Source Title
    Phytochemistry
    DOI
    10.1016/j.phytochem.2009.11.009
    ISSN
    00319422
    Faculty
    Department of Applied Chemistry
    School of Science and Computing
    Faculty of Science and Engineering
    Remarks

    Copyright © 2010 Elsevier B.V. All rights reserved

    URI
    http://hdl.handle.net/20.500.11937/14797
    Collection
    • Curtin Research Publications
    Abstract

    The n-fatty acids containing an even number of carbons (ECN-n-FAs) in higher plants are iosynthesisedby repetitive addition of a two carbon unit from malonyl-ACP. The n-alkanes containing an odd numberof carbon atoms (OCN-n-alkanes) are generally formed by the decarboxylation of ECN-n-FAs, but it isunknown how the less abundant even-carbon-numbered alkanes (ECN-n-alkanes) are biosynthesisedin higher plants. There is a distinctive compositional pattern of incorporation of stable carbon (13C) and hydrogen (2H) isotopes in co-existing ECN- and OCN-n-alkanes in leaves of higher plants, such that the OCN n-alkanes are relatively enriched in 13C but relatively depleted in 2H against the ECN-n-alkanes. This is consistent with the OCN-n-fatty acids having a propionate precursor which is derived from reduction of pyruvate. A tentative pathway is presented with propionate produced by enzymatic reduction of pyruvate which is then thio-esterified with CoSH (coenzyme A thiol) in the chloroplast to form the terminal precursor molecule propionyl-CoA. This is then repetitively extended/elongated with the 2-carbon unit from malonyl-ACP to form the long chain OCN-n-fatty acids. The anteiso- and iso-alkanes in Nicotiana tabacum leaf waxes have previously been found to be systematically enriched in 13C compared with the n-alkanes by Grice et al. (2008). This is consistent with the isotopic composition of their putative respective precursors (pyruvate as precursor for n-alkanes, valinefor iso-alkanes and isoleucine for anteiso-alkanes). The current study complements that of Grice et al.(2008) and looks at the distribution of hydrogen isotopes. The n-alkanes were found to be more enrichedin deuterium (2H) than the iso-alkanes which in turn were more enriched than the anteiso-alkanes. Wepropose therefore that the depletion of 2H in the iso-alkanes, relative to the n-alkanes is the consequence of accepting highly 2H-depleted hydrogen atoms from NADPH during their biosynthesis. The anteisoalkanes are further depleted again because there are three NADPH-derived hydrogen atoms in their precursor isoleucine, as compared with only one NADPH-derived hydrogen in valine, the precursor of the isoalkanes.

    Related items

    Showing items related by title, author, creator and subject.

    • Stable hydrogen isotope ratios of individual hydrocarbons in sediments and petroleum
      Dawson, Daniel (2006)
      Early research into the stable hydrogen isotopic compositions (δD) of petroleum involved bulk deuterium/hydrogen (D/H) measurements which, while providing some useful information, had to contend with the analysis of complex ...
    • Stable hydrogen isotopic composition of hydrocarbons in torbanites (Late Carboniferous to Late Permian) deposited under various climatic conditions
      Dawson, Daniel; Grice, Kliti; Wang, Sue; Alexander, Robert (2004)
      We measured the stable hydrogen isotopic composition (δD) of selected aliphatic compounds in torbanites from Scotland and Australia, covering the Late Carboniferous to the Late Permian. The torbanites contain organic ...
    • The organic geochemistry of marine-influenced coals.
      Sandison, Carolyn M. (2001)
      The importance of organic sulphur fixation in the preservation of organic matter in humic coal-forming environments is demonstrated in this thesis. The transgression of coal depositional systems by marine waters during ...
    Advanced search

    Browse

    Communities & CollectionsIssue DateAuthorTitleSubjectDocument TypeThis CollectionIssue DateAuthorTitleSubjectDocument Type

    My Account

    Admin

    Statistics

    Most Popular ItemsStatistics by CountryMost Popular Authors

    Follow Curtin

    • 
    • 
    • 
    • 
    • 

    CRICOS Provider Code: 00301JABN: 99 143 842 569TEQSA: PRV12158

    Copyright | Disclaimer | Privacy statement | Accessibility

    Curtin would like to pay respect to the Aboriginal and Torres Strait Islander members of our community by acknowledging the traditional owners of the land on which the Perth campus is located, the Whadjuk people of the Nyungar Nation; and on our Kalgoorlie campus, the Wongutha people of the North-Eastern Goldfields.