Elucidating the Structural Isomerism of Fluorescent Strigolactone Analogue CISA‐1 (Eur. J. Org. Chem. 6/2015). Issue 6 (February 2015)

• Record Type: Journal Article
• Authors: Goossens, Hannelore; Heugebaert, Thomas S. A.; Dereli, Busra; Van Overtveldt, Melissa; Karahan, Ozlem; Dogan, Ilknur; Waroquier, Michel; Van Speybroeck, Veronique; Aviyente, Viktorya; Catak, Saron; Stevens, Christian V.
• Is Part Of: European journal of organic chemistry. Issue 6(2015)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2015-02
• Subjects: Atropisomerism -- Lactones -- Conformation analysis -- Configuration determination -- Density functional calculations; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201590012
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : The cover picture shows the root uptake of CISA‐1, a new potent analogue of the plant hormone strigolactone and Striga lutea (witchweed), the parasitic weed in which strigolactones were first discovered. The inaccessibility of naturally occurring strigolactones and their structural complexity have led to synthetic efforts to produce bioactive analogues. The current study unravels the true identity of the interconverting structural isomers of CISA‐1 by using computational and experimental techniques and reports the first occurrence of atropisomers among strigolactone analogues. While the rate of interconversion for this specific derivative is sufficiently high to warrant full bioavailability, these findings are of high importance to the development of new analogues that could lead to stable atropisomers with different bioactivity. Details are discussed in the article by S. Catak, C. V. Stevens et al. on1211 ff .