Published: Journal of Chromatographic Science, Volume 36, Number 8, August 1998, pp. 388-394.

High Performance Liquid Chromatography on Calixarene-Bonded Silica Gels. III. Separations of cis/trans Isomers of Proline-Containing Peptides
Sabine Gebauer, Sieglinde Friebe, Gerd Scherer, Gerald Gübitz and Gerd-Joachim Krauss

The liquid chromatographic behavior of p-tert-butylcalix[n]arene (n = 4, 5, 6, and 8) for the separation of cis/trans peptide bond isomers of proline-containing peptides is studied to demonstrate the chromatographic selectivity of calixarene stationary phases. The results are compared with the elution patterns obtained on RP18 and b-cyclodextrin, as well as on a monomeric p-tert-butylphenoxyacetic acid. The chromatographic data are established by rechromatography and 1H-NMR spectroscopy. The results support the assumption that inclusion complexation seems to be a possible separation principle because of the size of the calixarene cavities.

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