2015
DOI: 10.1002/jssc.201500138
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Elucidation of the absolute configuration of rhizopine by chiral supercritical fluid chromatography and vibrational circular dichroism

Abstract: 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 … Show more

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Cited by 11 publications
(8 citation statements)
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“…Furthermore, (−)-1 l -3- O -MSI (−)-1 l - 2 promoted the growth of S. meliloti L5-30, whereas (+)-1 d -3- O -MSI ( + )-1d- 2 did not (Supplementary Fig. 4), supporting results from a recent study 21 . The confirmation of the chemical structure of rhizopines, and their secretion into the rhizosphere, provides a unique opportunity to use them as target molecules for engineering plant control of root bacteria.…”
Section: Resultssupporting
confidence: 87%
See 1 more Smart Citation
“…Furthermore, (−)-1 l -3- O -MSI (−)-1 l - 2 promoted the growth of S. meliloti L5-30, whereas (+)-1 d -3- O -MSI ( + )-1d- 2 did not (Supplementary Fig. 4), supporting results from a recent study 21 . The confirmation of the chemical structure of rhizopines, and their secretion into the rhizosphere, provides a unique opportunity to use them as target molecules for engineering plant control of root bacteria.…”
Section: Resultssupporting
confidence: 87%
“…1c, d). (−)-1 l -3- O -MSI (−)-1 l - 2 has previously been proposed to be the naturally occurring enantiomer 21 , and the preference for this enantiomer observed in Fig. 1c, d supports this.…”
Section: Resultssupporting
confidence: 61%
“…It followed that natural rhizopine is (1R,2S,3R,4R,5S,6R)−228 and its enantiomer is (1S,2R,3S,4S,5R,6S)−230, (Figure 63) while the peracetates are 229 and 231, respectively. 107 Commercial racemic butylone hydrochloride was separated into its enantiomers by chiral chromatographic. ECD and VCD, combined with DFT calculations provided the AC of both enantiomers as (S)-(232) and (R)-butylone (233) ( Figure 64).…”
Section: Nitrogenated Compoundsmentioning
confidence: 99%
“…It can be noted that the introduction of a distribution for the the central wavenumber ν 0,k corresponds to considering a family of peaks close to the peak of the plain calculation, and thus leads to broadened spectra, just as happens in the neighborhood similarity approach. [23,24] The variances on the parameters have been estimated from 8 computations ad different level of theory, used in previous successful works on VCD spectroscopy of small organic molecules: B3LYP/TZ2P, [25] B3LYP/cc-PVTZ, [13,25,26] B3LYP/6-31G*, [27] B3PW91/TZ2P, [25] B3PW91/cc-PVTZ, [25,26] B97D/TZ2P, [28] ω-B97XD/6-31G*, [27] ω-B97XD/6-311++G**, [29] using in all cases the PCM model, [30] to model the effect of chloroform. Final standard deviations proposed were σ(ν 0 ) = 10 cm −1 , σ(µ) = 2 • 10 −20 esu cm, σ(m) = 1.5 • 10 −24 esu cm, σ(ξ) = 10 • .…”
Section: Theorymentioning
confidence: 99%