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Title
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Elucidation of the absolute configuration of rhizopine by chiral supercritical fluid chromatography and vibrational circular dichroism
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Author
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Abstract
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| 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. |
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Language
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English
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Source (journal)
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Journal of separation science. - Weinheim, 2001, currens
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Publication
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Weinheim
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2015
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ISSN
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1615-9306
[print]
1615-9314
[online]
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DOI
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10.1002/JSSC.201500138
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Volume/pages
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38
:14
(2015)
, p. 2545-2550
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ISI
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000358001000022
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Pubmed ID
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25931280
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Full text (Publisher's DOI)
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Full text (publisher's version - intranet only)
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