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- Title
Elucidation of the absolute configuration of rhizopine by chiral supercritical fluid chromatography and vibrational circular dichroism.
- Authors
Krief, Alain; Dunkle, Melissa; Bahar, Masoud; Bultinck, Patrick; Herrebout, Wouter; Sandra, Pat
- 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 (1 R,2 S,3 R,4 R,5 S,6 R)-4-amino-6-methoxycyclohexane-1,2,3,5-tetraol.
- Subjects
VIBRATIONAL circular dichroism; SUPERCRITICAL fluid chromatography; RHIZOBIUM leguminosarum; NITROGEN-fixing plants; INFRARED spectroscopy; ENANTIOMERS
- Publication
Journal of Separation Science, 2015, Vol 38, Issue 14, p2545
- ISSN
1615-9306
- Publication type
Article
- DOI
10.1002/jssc.201500138