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Dissociation of proton-bound complexes reveals geometry and arrangement of double bonds in unsaturated lipids

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  • معلومة اضافية
    • بيانات النشر:
      Elsevier
    • الموضوع:
      2015
    • Collection:
      Queensland University of Technology: QUT ePrints
    • نبذة مختصرة :
      Double bond position and stereochemistry in unsaturated lipids can have profound impact on biological properties and activities but the assignment of these features by mass spectrometry is frequently challenging. Conventional techniques for lipid identification rely on collision-induced dissociation (CID) and are most often unable to differentiate between lipid isomers, particularly those involving double bond position and geometry (i.e., cis and trans). In this study, CID performed on proton-bound complexes of fatty acid methyl esters and iodoaniline (and related reagents) reveals unusual fragmentation patterns. CID products are shown to result from proton transfer and are associated with specific structures of the unsaturated lipids. Notably, CID of these complexes can not only distinguish cis- and trans-fatty acid methyl esters, but also differentiate conjugated double bond arrangements from non-conjugated analogs. Herein, the mechanisms underpinning this unique CID behavior are investigated by stable isotope labeling and are proposed to involve both carbene and free radical intermediates.
    • File Description:
      application/pdf
    • Relation:
      https://eprints.qut.edu.au/96428/1/Pham_etal_RevisedManuscript_13JUL2015.pdf; Pham, Huong, Prendergast, Matthew, Dunstan, Christopher, Trevitt, Adam, Mitchell, Todd, Julian, Ryan, & Blanksby, Stephen (2015) Dissociation of proton-bound complexes reveals geometry and arrangement of double bonds in unsaturated lipids. International Journal of Mass Spectrometry, 390, pp. 170-177.; http://purl.org/au-research/grants/arc/DP150101715; http://purl.org/au-research/grants/arc/CE0561607; https://eprints.qut.edu.au/96428/; Institute for Future Environments; Science & Engineering Faculty; School of Chemistry, Physics & Mechanical Engineering
    • الدخول الالكتروني :
      https://eprints.qut.edu.au/96428/
    • Rights:
      free_to_read ; http://creativecommons.org/licenses/by-nc-nd/2.5/ ; Consult author(s) regarding copyright matters ; This work is covered by copyright. Unless the document is being made available under a Creative Commons Licence, you must assume that re-use is limited to personal use and that permission from the copyright owner must be obtained for all other uses. If the document is available under a Creative Commons License (or other specified license) then refer to the Licence for details of permitted re-use. It is a condition of access that users recognise and abide by the legal requirements associated with these rights. If you believe that this work infringes copyright please provide details by email to qut.copyright@qut.edu.au
    • الرقم المعرف:
      edsbas.541A878A