Critical remarks on the-interpretation of chiral stereodifferentiation in gas chromatography

Deger, Wolfgang; Gessner, Martin; Heusinger, Georg; Singer, G.; Mosandl, Armin

doi:10.1016/s0021-9673(01)93488-0

Cited by 17 publications

(4 citation statements)

References 10 publications

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“…Referring to recently published results (Deger et al, 1986; , this paper demonstrates that Instituí für Pharmazie und Lebensmittelchemie, Universitát Würzburg, Am Hubland, D-8700 Würzburg, West Germany.…”

supporting

confidence: 72%

“…With (E)-(+)-l-phenylethyl isocyanate as a chiral auxiliary reagent and racemic alkan-2-ols, the resulting carbamates are resolved on the achiral phase DB 210-30 W. The order of elution was determined with synthesized optically pure references for each pair of diastereoisomers (Deger et al, 1986;Deger, 1988). Within this series of homologues, the order of elution is R,S (first) and R,R (second).…”

Section: Resultsmentioning

confidence: 99%

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Stereoisomeric flavor compounds. 18. Enantiodiscrimination of chiral flavor compounds by diastereomeric derivatization

Deger¹,

Gessner²,

Guenther³

et al. 1988

J. Agric. Food Chem.

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supporting

confidence: 72%

Section: Resultsmentioning

confidence: 99%

Stereoisomeric flavor compounds. 18. Enantiodiscrimination of chiral flavor compounds by diastereomeric derivatization

Deger¹,

Gessner²,

Guenther³

et al. 1988

J. Agric. Food Chem.

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“…For the analysis of chiral alkan-2-ols, their reactivity with chiral isocyanates to yield diastereomeric carbamates was supposed to be a suitable method for estimation of their optical purity (53,54). With (i?…”

Section: Methods 1: Indirect Analysis Via Diastereoisomersmentioning

confidence: 99%

“…With Chirasil-Val (applicable between 30° and 230°C) all the four stereoisomers of. cw-2-methyl-4-propyl-S-oxides (15a, 15a', 15b, 15b') are separable without any derivatization (54,56). The correlation between absolute configuration and the order of emergence was elucidated by mixing different quantities of optically pure equatorial/axial (3:1) sulfoxides.…”

Section: Methods 3: Direct Analysis On Chiral Stationary Phasementioning

confidence: 99%

Chirality in flavor chemistry‐recent developments in synthesis and analysis

Mosandl

1988

Food Reviews International

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The state of the art in research on chirality and odor is presented, with special emphasis on synthetic and analytical methods. The syntheses of l-octen-3-ol enantiomers, of chiral alkan-2-yl esters, of "whisky lactone," and of chiral sulfur compounds, known as characteristic components of the yellow passion fruit, are reviewed. It is demonstrated that optically pure stereoisomers exhibit their own, specific sensory characteristics. Therefore, stereoisomers of very high enantiomeric excess (ee) must be achieved for valid evaluations of their structure-function relationships. Analytical methods for stereodifferentiation of chiral flavor compounds and recent developments in biotechnology are discussed.

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