Insights into the formation of carlactone from in-depth analysis of the CCD8-catalyzed reactions
van der Steen, Rob
KAUST DepartmentBiological and Environmental Sciences and Engineering (BESE) Division
Desert Agriculture Initiative
Online Publication Date2017-03-09
Print Publication Date2017-03
Permanent link to this recordhttp://hdl.handle.net/10754/622920
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AbstractStrigolactones (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.
CitationBruno 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.
SponsorsWe 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).