Elucidation of the absolute configuration of rhizopine by chiral supercritical fluid chromatography and vibrational circular dichroism.
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.
Department of Chemistry, University of Namur, Namur, Belgium.
Alain
A
Krief
Research Institute for Chromatography (R.I.C.), Kortrijk, Belgium.
Melissa
M
Dunkle
Department of Plant Protection & Agricultural Biotechnology, College of Agriculture, Isfahan University of Technology, Isfahan, Iran.
Masoud
M
Bahar
Department of Inorganic and Physical Chemistry, Ghent University, Krijgslaan 281 (S3), Ghent, Belgium.|Scaldis Spectroscopy, www.scaldis-spectroscopy.com.
Patrick
P
Bultinck
Scaldis Spectroscopy, www.scaldis-spectroscopy.com.|Department of Chemistry, University of Antwerp, Antwerp, Belgium.
Wouter
W
Herrebout
Research Institute for Chromatography (R.I.C.), Kortrijk, Belgium.
Pat
P
Sandra
D025924:Chromatography, Supercritical Fluid / Q000379:methods*; D002942:Circular Dichroism / Q000379:methods*; D007294:Inositol / Q000031:analogs & derivatives* / Q000737:chemistry; D000455:Medicago sativa / Q000382:microbiology; D008968:Molecular Conformation; D015394:Molecular Structure; D012231:Rhizobium; D012997:Solvents; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism; D014732:Vibration
D012997:Solvents; C082577:rhizopine; D007294:Inositol
Absolute configuration/Infrared spectroscopy/Rhizopine/Supercritical fluid chromatography/Vibrational circular dichroism