Elucidation of the absolute configuration of rhizopine by chiral supercritical fluid chromatography and vibrational circular dichroism. Issue 14 (7th July 2015)

• Record Type: Journal Article
• Authors: Krief, Alain; Dunkle, Melissa; Bahar, Masoud; Bultinck, Patrick; Herrebout, Wouter; Sandra, Pat
• Is Part Of: Journal of separation science. Volume 38:Issue 14(2015:Jul.)
• Page Start: 2545
• Page End: 2550
• Publication Date: 2015-07-07
• Subjects: Separation (Technology) -- Periodicals; Chromatographic analysis -- Periodicals; 543.089
• DOI: 10.1002/jssc.201500138
• Languages: English
• ISSNs: 1615-9306

Abstract

<abstract abstract-type="main"> <title> <x xml:space="preserve">Abstract</x> </title> <p>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<italic>R</italic>, 2<italic>S</italic>, 3<italic>R</italic>, 4<italic>R</italic>, 5<italic>S</italic>, 6<italic>R</italic>)‐4‐amino‐6‐methoxycyclohexane‐1, 2, 3, 5‐tetraol.</p> </abstract>