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

Krief Alain | Zendy; Dunkle Melissa | Zendy; Bahar Masoud | Zendy; Bultinck Patrick | Zendy; Herrebout Wouter | Zendy; Sandra Pat | Zendy

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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.

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