Chiroptical detection during liquid chromatography 7

Brandl, Friedrich; Pustet, Nikola; Mannschreck, Albrecht

doi:10.1016/s0021-9673(00)01105-5

Cited by 17 publications

(5 citation statements)

References 24 publications

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“…Chiroptical detection during liquid chromatography was performed using the Jasco CD-1595 detector (Jasco International Co., Ltd., Tokyo, Japan), which provides the differential absorbance Δ A of the CD and the absorbance A of the UV mode simultaneously as a function of time. The analog experimental data were monitored by the two-channel recorder Asea Brown Boveri SE 120 or digitized and processed using the computer program SEPP. , Simultaneous detection of the CD and the UV signals was carried out with a flow-through cell (25 mm) at the single wavelength of 240 nm. The spectra (220−420 nm) were recorded by a stopped-flow method 21 under the same conditions.…”

Section: Methodsmentioning

confidence: 99%

In Vitro Biotransformation of (R)-and (S)-Thalidomide: Application of Circular Dichroism Spectroscopy to the Stereochemical Characterization of the Hydroxylated Metabolites

et al. 2002

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Circular dichroism (CD) spectroscopy was successfully used for the stereochemical characterization of the hydroxylated metabolites formed during the in vitro biotransformation of (R)- and (S)-thalidomide. Incubation extracts of the individual enantiomers were analyzed by HPLC on an achiral stationary phase combined with CD detection. The CD data of the almost enantiopure eluates of the metabolites were compared with the CD spectra quantum chemically calculated for the respective structures. The results allowed us a reliable determination of the absolute stereostructure for all of the metabolites. The chiral center of thalidomide is unaffected by the stereoselective biotransformation process. (3'R,5'R)-trans-5'-hydroxythalidomide is the main metabolite of (R)-thalidomide, which epimerizes spontaneously to give the more stable (3'S,5'R)-cis isomer. On the contrary, (S)-thalidomide is preferentially metabolized by hydroxylation in the phthalimide moiety, resulting in the formation of (S)-5-hydroxythalidomide.

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Section: Methodsmentioning

confidence: 99%

In Vitro Biotransformation of (R)-and (S)-Thalidomide: Application of Circular Dichroism Spectroscopy to the Stereochemical Characterization of the Hydroxylated Metabolites

et al. 2002

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“…For the racemate, two peaks with equal areas are found (Figure 4). Another sample shows one peak for (S )-carvone in the chromatogram (14); that is, it is enantiomerically pure. t R / min 20.9…”

Section: Separation Of Enantiomers By Chromatographymentioning

confidence: 99%

Differentiations of Enantiomers via Their Diastereomeric Association Complexes—There Are Two Ways of Shaking Hands

Mannschreck

Kiesswetter

2005

J. Chem. Educ.

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The intermolecular interactions of one enantiomer with a chiral auxiliary molecule and the interactions of the other enantiomer with the auxiliary are considered. Different functions of the latter give rise to the following well-known aspects of organic stereochemistry that are characterized in the present article: (i) preparative separation of enantiomers via crystallization of diastereomeric salts; (ii) analysis of enantiomers by NMR spectroscopy; (iii) separation of enantiomers by chromatography; (iv) biological activities of enantiomers; and (v) reactivities of enantiomers in enzymatic resolution. The common basis of these aspects is the formation of two diastereomeric association complexes that may differ with respect to their physical and chemical properties. The following practical applications of this phenomenon are briefly described: the small- and large-scale preparation of the enantiomers of organic compounds; the analysis of chiral nonracemic mixtures by chromatography and by NMR spectroscopy; and the growing use of drugs in the form of one of the enantiomers. It is proposed to emphasize the similarity of the association-based differentiations. This goal can be attained by giving a corresponding lecture in the second or third year of university chemistry.

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“…The acquisition of circular dichroism spectra during LC means that racemates can be applied instead of the antipodes, provided an analytical LC separation is accomplished. Advantage of this technique is its ability to determine relative configurations of interconvertible enantiomers [71][72][73].…”

Section: Chiroptical Detectionmentioning

confidence: 99%

Role of biological matrices during the analysis of chiral drugs by liquid chromatography

Mislanova

Hutta

2003

Journal of Chromatography B

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Chiroptical detection during liquid chromatography 7

Cited by 17 publications

References 24 publications

In Vitro Biotransformation of (R)-and (S)-Thalidomide: Application of Circular Dichroism Spectroscopy to the Stereochemical Characterization of the Hydroxylated Metabolites

In Vitro Biotransformation of (R)-and (S)-Thalidomide: Application of Circular Dichroism Spectroscopy to the Stereochemical Characterization of the Hydroxylated Metabolites

Differentiations of Enantiomers via Their Diastereomeric Association Complexes—There Are Two Ways of Shaking Hands

Role of biological matrices during the analysis of chiral drugs by liquid chromatography

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