Elucidation of the absolute configuration of rhizopine by chiral supercritical fluid chromatography and vibrational circular dichroism |
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| Authors: | Alain Krief Melissa Dunkle Masoud Bahar Patrick Bultinck Wouter Herrebout Pat Sandra |
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| Institution: | 1. Department of Chemistry, University of Namur, Namur, Belgium;2. Research Institute for Chromatography (R.I.C.), Kortrijk, Belgium;3. Department of Plant Protection & Agricultural Biotechnology, College of Agriculture, Isfahan University of Technology, Isfahan, Iran;4. Department of Inorganic and Physical Chemistry, Ghent University, Ghent, Belgium;5. Scaldis Spectroscopywww.scaldis‐spectroscopy.com;6. Department of Chemistry, University of Antwerp, Antwerp, Belgium |
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| Abstract: | The absolute configuration of rhizopine, an opine‐like natural product present in nitrogen‐fixing nodules of alfalfa infected by rhizobia, is elucidated using a combination of state‐of‐the‐art analytical and semi‐preparative supercritical fluid chromatography and vibrational circular dichroism spectroscopy. A synthetic peracetylated racemate was fractionated into its enantiomers and subjected to absolute configuration analysis revealing that natural rhizopine exists as a single enantiomer. The stereochemistry of non‐derivatized natural rhizopine corresponds to (1R,2S,3R,4R,5S,6R)‐4‐amino‐6‐methoxycyclohexane‐1,2,3,5‐tetraol. |
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| Keywords: | Absolute configuration/Infrared spectroscopy/Rhizopine/Supercritical fluid chromatography/Vibrational circular dichroism |
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