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Elucidating the structural isomerism of fluorescent strigolactone analogue CISA-1

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Abstract
The synthesis of a new potent strigolactone analogue (CISA-1), resulting in the formation of two interconverting structural isomers, which could not be identified, was recently reported. In the present study, a combined computational and experimental approach is used to identify the exact nature of these structural isomers. Although standard experimental techniques could not be used to determine the identity of the isomers, chromatographic methods excluded E/Z isomerisation. Computational H-1 NMR chemical shift values and DFT calculations on interconversion barriers strongly suggest that the CISA-1 isomers were interconverting (Z)-configured atropisomers.
Keywords
Configuration determination, Density functional calculations, Conformation analysis, Lactones, Atropisomerism, STRIGA-LUTEA LOUR, GERMINATION STIMULANTS, CHEMICAL-SHIFTS, PLANT HORMONES, OROBANCHE, DENSITY, THERMOCHEMISTRY, ENERGIES, MODEL, GR24

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Citation

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Chicago
Goossens, Hannelore, Thomas Heugebaert, Busra Dereli, Melissa Van Overtveldt, Ozlem Karahan, Ilknur Dogan, Michel Waroquier, et al. 2015. “Elucidating the Structural Isomerism of Fluorescent Strigolactone Analogue CISA-1.” European Journal of Organic Chemistry (6): 1211–1217.
APA
Goossens, Hannelore, Heugebaert, T., Dereli, B., Van Overtveldt, M., Karahan, O., Dogan, I., Waroquier, M., et al. (2015). Elucidating the structural isomerism of fluorescent strigolactone analogue CISA-1. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (6), 1211–1217.
Vancouver
1.
Goossens H, Heugebaert T, Dereli B, Van Overtveldt M, Karahan O, Dogan I, et al. Elucidating the structural isomerism of fluorescent strigolactone analogue CISA-1. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. 2015;(6):1211–7.
MLA
Goossens, Hannelore, Thomas Heugebaert, Busra Dereli, et al. “Elucidating the Structural Isomerism of Fluorescent Strigolactone Analogue CISA-1.” EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 6 (2015): 1211–1217. Print.
@article{5944648,
  abstract     = {The synthesis of a new potent strigolactone analogue (CISA-1), resulting in the formation of two interconverting structural isomers, which could not be identified, was recently reported. In the present study, a combined computational and experimental approach is used to identify the exact nature of these structural isomers. Although standard experimental techniques could not be used to determine the identity of the isomers, chromatographic methods excluded E/Z isomerisation. Computational H-1 NMR chemical shift values and DFT calculations on interconversion barriers strongly suggest that the CISA-1 isomers were interconverting (Z)-configured atropisomers.},
  author       = {Goossens, Hannelore and Heugebaert, Thomas and Dereli, Busra and Van Overtveldt, Melissa and Karahan, Ozlem and Dogan, Ilknur and Waroquier, Michel and Van Speybroeck, Veronique and Aviyente, Viktorya and Catak, Saron and Stevens, Christian},
  issn         = {1434-193X},
  journal      = {EUROPEAN JOURNAL OF ORGANIC CHEMISTRY},
  language     = {eng},
  number       = {6},
  pages        = {1211--1217},
  title        = {Elucidating the structural isomerism of fluorescent strigolactone analogue CISA-1},
  url          = {http://dx.doi.org/10.1002/ejoc.201403457},
  year         = {2015},
}

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