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Elucidation of the absolute configuration of rhizopine by chiral supercritical fluid chromatography and vibrational circular dichroism

Alain Krief, Melissa Dunkle, Masoud Bahar, Patrick Bultinck (UGent) , Wouter Herrebout and Patrick Sandra (UGent)
(2015) JOURNAL OF SEPARATION SCIENCE. 38(14). p.2545-2550
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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.
Keywords
Absolute configuration, Infrared spectroscopy, Rhizopine, Supercritical fluid chromatography, Vibrational circular dichroism, MONOTERPENE CHROMANE ESTERS, OPINE-LIKE COMPOUND, OPTICAL-ACTIVITY, NATURAL-PRODUCT, VCD, MELILOTI, NODULES

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MLA
Krief, Alain et al. “Elucidation of the Absolute Configuration of Rhizopine by Chiral Supercritical Fluid Chromatography and Vibrational Circular Dichroism.” JOURNAL OF SEPARATION SCIENCE 38.14 (2015): 2545–2550. Print.
APA
Krief, A., Dunkle, M., Bahar, M., Bultinck, P., Herrebout, W., & Sandra, P. (2015). Elucidation of the absolute configuration of rhizopine by chiral supercritical fluid chromatography and vibrational circular dichroism. JOURNAL OF SEPARATION SCIENCE, 38(14), 2545–2550.
Chicago author-date
Krief, Alain, Melissa Dunkle, Masoud Bahar, Patrick Bultinck, Wouter Herrebout, and Patrick Sandra. 2015. “Elucidation of the Absolute Configuration of Rhizopine by Chiral Supercritical Fluid Chromatography and Vibrational Circular Dichroism.” Journal of Separation Science 38 (14): 2545–2550.
Chicago author-date (all authors)
Krief, Alain, Melissa Dunkle, Masoud Bahar, Patrick Bultinck, Wouter Herrebout, and Patrick Sandra. 2015. “Elucidation of the Absolute Configuration of Rhizopine by Chiral Supercritical Fluid Chromatography and Vibrational Circular Dichroism.” Journal of Separation Science 38 (14): 2545–2550.
Vancouver
1.
Krief A, Dunkle M, Bahar M, Bultinck P, Herrebout W, Sandra P. Elucidation of the absolute configuration of rhizopine by chiral supercritical fluid chromatography and vibrational circular dichroism. JOURNAL OF SEPARATION SCIENCE. 2015;38(14):2545–50.
IEEE
[1]
A. Krief, M. Dunkle, M. Bahar, P. Bultinck, W. Herrebout, and P. Sandra, “Elucidation of the absolute configuration of rhizopine by chiral supercritical fluid chromatography and vibrational circular dichroism,” JOURNAL OF SEPARATION SCIENCE, vol. 38, no. 14, pp. 2545–2550, 2015.
@article{6914094,
  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.},
  author       = {Krief, Alain and Dunkle, Melissa and Bahar, Masoud and Bultinck, Patrick and Herrebout, Wouter and Sandra, Patrick},
  issn         = {1615-9306},
  journal      = {JOURNAL OF SEPARATION SCIENCE},
  keywords     = {Absolute configuration,Infrared spectroscopy,Rhizopine,Supercritical fluid chromatography,Vibrational circular dichroism,MONOTERPENE CHROMANE ESTERS,OPINE-LIKE COMPOUND,OPTICAL-ACTIVITY,NATURAL-PRODUCT,VCD,MELILOTI,NODULES},
  language     = {eng},
  number       = {14},
  pages        = {2545--2550},
  title        = {Elucidation of the absolute configuration of rhizopine by chiral supercritical fluid chromatography and vibrational circular dichroism},
  url          = {http://dx.doi.org/10.1002/jssc.201500138},
  volume       = {38},
  year         = {2015},
}
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