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    Insights into the formation of carlactone from in-depth analysis of the CCD8-catalyzed reactions

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    Type
    Article
    Authors
    Bruno, Mark
    Vermathen, Martina
    Alder, Adrian
    Wüst, Florian
    Schaub, Patrick
    van der Steen, Rob
    Beyer, Peter
    Ghisla, Sandro
    Al-Babili, Salim cc
    KAUST Department
    Biological and Environmental Science and Engineering (BESE) Division
    Center for Desert Agriculture
    Plant Science
    Date
    2017-03-09
    Online Publication Date
    2017-03-09
    Print Publication Date
    2017-03
    Permanent link to this record
    http://hdl.handle.net/10754/622920
    
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    Abstract
    Strigolactones (SLs) are a new class of phytohormones synthesized from carotenoids via carlactone. The complex structure of carlactone is not easily deducible from its precursor, a cis-configured β-carotene cleavage product, and is thus formed via a poorly understood series of reactions and molecular rearrangements, all catalyzed by only one enzyme, the carotenoid cleavage dioxygenase 8 (CCD8). Moreover, the reactions leading to carlactone are expected to form a second, yet unidentified product. In this study, we used (13) C and (18) O-labelling to shed light on the reactions catalyzed by CCD8. The characterization of the resulting carlactone by LC-MS and NMR, and the identification of the assumed, less accessible second product allowed us to formulate a minimal reaction mechanism for carlactone generation. This article is protected by copyright. All rights reserved.
    Citation
    Bruno M, Vermathen M, Alder A, Wüst F, Schaub P, et al. (2017) Insights into the formation of carlactone from in-depth analysis of the CCD8-catalyzed reactions. FEBS Letters. Available: http://dx.doi.org/10.1002/1873-3468.12593.
    Sponsors
    We thank Dr. S. Schürch (University of Bern, Switzerland) for the MS-spectra of 18O-labeled carlactone, and Prof. Dr. A Bacher, (TU München, Germany) for most helpful comments. Research reported in this publication was supported by the King Abdullah University of Science and Technology (KAUST).
    Publisher
    Wiley
    Journal
    FEBS Letters
    DOI
    10.1002/1873-3468.12593
    Additional Links
    http://onlinelibrary.wiley.com/doi/10.1002/1873-3468.12593/abstract;jsessionid=F22B83C31F6B487F760B102EC5E8F6A9.f03t04
    ae974a485f413a2113503eed53cd6c53
    10.1002/1873-3468.12593
    Scopus Count
    Collections
    Articles; Biological and Environmental Science and Engineering (BESE) Division; Center for Desert Agriculture

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