TY - JOUR
T1 - Insights into the formation of carlactone from in-depth analysis of the CCD8-catalyzed reactions
AU - Bruno, Mark
AU - Vermathen, Martina
AU - Alder, Adrian
AU - Wüst, Florian
AU - Schaub, Patrick
AU - van der Steen, Rob
AU - Beyer, Peter
AU - Ghisla, Sandro
AU - Al-Babili, Salim
N1 - KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: 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).
PY - 2017/3/9
Y1 - 2017/3/9
N2 - 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.
AB - 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.
UR - http://hdl.handle.net/10754/622920
UR - http://onlinelibrary.wiley.com/doi/10.1002/1873-3468.12593/abstract;jsessionid=F22B83C31F6B487F760B102EC5E8F6A9.f03t04
UR - http://www.scopus.com/inward/record.url?scp=85014967551&partnerID=8YFLogxK
U2 - 10.1002/1873-3468.12593
DO - 10.1002/1873-3468.12593
M3 - Article
C2 - 28186640
SN - 0014-5793
VL - 591
SP - 792
EP - 800
JO - FEBS Letters
JF - FEBS Letters
IS - 5
ER -