On the substrate- and stereospecificity of the plant carotenoid cleavage dioxygenase 7

Mark Bruno; Manuel Hofmann; Martina Vermathen; Adrian Alder; Peter D. Beyer; Salim Al-Babili

doi:10.1016/j.febslet.2014.03.041

On the substrate- and stereospecificity of the plant carotenoid cleavage dioxygenase 7

Mark Bruno, Manuel Hofmann, Martina Vermathen, Adrian Alder, Peter D. Beyer, Salim Al-Babili

Research output: Contribution to journal › Article › peer-review

68 Scopus citations

Abstract

Strigolactones are phytohormones synthesized from carotenoids via a stereospecific pathway involving the carotenoid cleavage dioxygenases 7 (CCD7) and 8. CCD7 cleaves 9-cis-β-carotene to form a supposedly 9-cis-configured β-apo-10′-carotenal. CCD8 converts this intermediate through a combination of yet undetermined reactions into the strigolactone-like compound carlactone. Here, we investigated the substrate and stereo-specificity of the Arabidopsis and pea CCD7 and determined the stereo-configuration of the β-apo-10′-carotenal intermediate by using Nuclear Magnetic Resonance Spectroscopy. Our data unequivocally demonstrate the 9-cis-configuration of the intermediate. Both CCD7s cleave different 9-cis-carotenoids, yielding hydroxylated 9-cis-apo-10′-carotenals that may lead to hydroxylated carlactones, but show highest affinity for 9-cis-β-carotene. © 2014 Federation of European Biochemical Societies. Published by Elsevier B.V. All rights reserved.

Original language	English (US)
Pages (from-to)	1802-1807
Number of pages	6
Journal	FEBS Letters
Volume	588
Issue number	9
DOIs	https://doi.org/10.1016/j.febslet.2014.03.041
State	Published - Mar 28 2014

ASJC Scopus subject areas

Biochemistry
Structural Biology
Cell Biology
Genetics
Molecular Biology
Biophysics

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title = "On the substrate- and stereospecificity of the plant carotenoid cleavage dioxygenase 7",

abstract = "Strigolactones are phytohormones synthesized from carotenoids via a stereospecific pathway involving the carotenoid cleavage dioxygenases 7 (CCD7) and 8. CCD7 cleaves 9-cis-β-carotene to form a supposedly 9-cis-configured β-apo-10′-carotenal. CCD8 converts this intermediate through a combination of yet undetermined reactions into the strigolactone-like compound carlactone. Here, we investigated the substrate and stereo-specificity of the Arabidopsis and pea CCD7 and determined the stereo-configuration of the β-apo-10′-carotenal intermediate by using Nuclear Magnetic Resonance Spectroscopy. Our data unequivocally demonstrate the 9-cis-configuration of the intermediate. Both CCD7s cleave different 9-cis-carotenoids, yielding hydroxylated 9-cis-apo-10′-carotenals that may lead to hydroxylated carlactones, but show highest affinity for 9-cis-β-carotene. {\textcopyright} 2014 Federation of European Biochemical Societies. Published by Elsevier B.V. All rights reserved.",

author = "Mark Bruno and Manuel Hofmann and Martina Vermathen and Adrian Alder and Beyer, {Peter D.} and Salim Al-Babili",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: This work was supported by the German Research Foundation (DFG) Grant AL 892/1-4 and by the EU (METAPRO; FP7 KBBE-2009-3-1-01).",

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AU - Vermathen, Martina

AU - Alder, Adrian

AU - Beyer, Peter D.

AU - Al-Babili, Salim

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: This work was supported by the German Research Foundation (DFG) Grant AL 892/1-4 and by the EU (METAPRO; FP7 KBBE-2009-3-1-01).

PY - 2014/3/28

Y1 - 2014/3/28

N2 - Strigolactones are phytohormones synthesized from carotenoids via a stereospecific pathway involving the carotenoid cleavage dioxygenases 7 (CCD7) and 8. CCD7 cleaves 9-cis-β-carotene to form a supposedly 9-cis-configured β-apo-10′-carotenal. CCD8 converts this intermediate through a combination of yet undetermined reactions into the strigolactone-like compound carlactone. Here, we investigated the substrate and stereo-specificity of the Arabidopsis and pea CCD7 and determined the stereo-configuration of the β-apo-10′-carotenal intermediate by using Nuclear Magnetic Resonance Spectroscopy. Our data unequivocally demonstrate the 9-cis-configuration of the intermediate. Both CCD7s cleave different 9-cis-carotenoids, yielding hydroxylated 9-cis-apo-10′-carotenals that may lead to hydroxylated carlactones, but show highest affinity for 9-cis-β-carotene. © 2014 Federation of European Biochemical Societies. Published by Elsevier B.V. All rights reserved.

AB - Strigolactones are phytohormones synthesized from carotenoids via a stereospecific pathway involving the carotenoid cleavage dioxygenases 7 (CCD7) and 8. CCD7 cleaves 9-cis-β-carotene to form a supposedly 9-cis-configured β-apo-10′-carotenal. CCD8 converts this intermediate through a combination of yet undetermined reactions into the strigolactone-like compound carlactone. Here, we investigated the substrate and stereo-specificity of the Arabidopsis and pea CCD7 and determined the stereo-configuration of the β-apo-10′-carotenal intermediate by using Nuclear Magnetic Resonance Spectroscopy. Our data unequivocally demonstrate the 9-cis-configuration of the intermediate. Both CCD7s cleave different 9-cis-carotenoids, yielding hydroxylated 9-cis-apo-10′-carotenals that may lead to hydroxylated carlactones, but show highest affinity for 9-cis-β-carotene. © 2014 Federation of European Biochemical Societies. Published by Elsevier B.V. All rights reserved.

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On the substrate- and stereospecificity of the plant carotenoid cleavage dioxygenase 7

Abstract

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