Insights into the formation of carlactone from in-depth analysis of the CCD8-catalyzed reactions
Type
ArticleAuthors
Bruno, MarkVermathen, Martina
Alder, Adrian
Wüst, Florian
Schaub, Patrick
van der Steen, Rob
Beyer, Peter
Ghisla, Sandro
Al-Babili, Salim

KAUST Department
Biological and Environmental Science and Engineering (BESE) DivisionCenter for Desert Agriculture
Plant Science
Date
2017-03-09Online Publication Date
2017-03-09Print Publication Date
2017-03Permanent link to this record
http://hdl.handle.net/10754/622920
Metadata
Show full item recordAbstract
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
WileyJournal
FEBS LettersAdditional Links
http://onlinelibrary.wiley.com/doi/10.1002/1873-3468.12593/abstract;jsessionid=F22B83C31F6B487F760B102EC5E8F6A9.f03t04ae974a485f413a2113503eed53cd6c53
10.1002/1873-3468.12593