Chiral recognition of peptide enantiomers by cinchona alkaloid derived chiral selectors: mechanistic investigations by liquid chromatography, NMR spectroscopy, and …

C Czerwenka, MM Zhang, H Kählig…

Index: Czerwenka, Christoph; Zhang, Mei Mei; Kaehlig, Hanspeter; Maier, Norbert M.; Lipkowitz, Kenny B.; Lindner, Wolfgang Journal of Organic Chemistry, 2003 , vol. 68, # 22 p. 8315 - 8327

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Citation Number: 58

Abstract

The chiral recognition mechanism of a cinchona alkaloid based chiral selector for N- protected peptide enantiomers was investigated. A chiral stationary phase derived from this selector was employed for liquid chromatographic enantiomer separations. It showed exceptionally high enantiomer discrimination for the (all-R)-and (all-S)-enantiomers of dialanine (α= 20), while a pronounced loss of chiral recognition occurred upon the ...