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Elucidation of the absolute configuration of rhizopine by chiral supercritical fluid chromatography and vibrational circular dichroism
Author(s) -
Krief Alain,
Dunkle Melissa,
Bahar Masoud,
Bultinck Patrick,
Herrebout Wouter,
Sandra Pat
Publication year - 2015
Publication title -
journal of separation science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.72
H-Index - 102
eISSN - 1615-9314
pISSN - 1615-9306
DOI - 10.1002/jssc.201500138
Subject(s) - absolute configuration , chemistry , circular dichroism , enantiomer , supercritical fluid chromatography , supercritical fluid , vibrational circular dichroism , chromatography , cotton effect , chiral column chromatography , spectroscopy , enantiomeric excess , stereochemistry , high performance liquid chromatography , analytical chemistry (journal) , organic chemistry , enantioselective synthesis , catalysis , physics , quantum mechanics
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.