The first FABMS study of the enantioselectivity shown during complex formation between per-methylated cyclodextrins and pairs of enantiomeric guest molecules is described. The 1:1 mixtures of the cyclodextrins, both α- and β-, with the guests, the methyl esters of the amino acids tryptophan and phenylalanine, were studied in a 100:50:1 glycerol-thioglycerol-trifluoro-acetic acid matrix. The uncomplexed cyclodextrin peaks were then used as internal standards to determine the preference of the cavity for one or other of the enantiomers. A clear trend for the preferential binding, greater than 5:1 in each case, of the d-enantiomers of the amino acid esters was observed in agreement with literature 1H NMR experiments. This methodology provides a rapid route to assessing the enantioselectivity shown by the widely used cyclodextrins towards pairs of enantiomeric guests.

Fast atom bombardment mass spectrometry as a tool for the rapid determination of enantioselective binding of methylated cyclodextrins / Si. N. Davey;D. A. Leigh;J. P. Smart;L.W. Tetler;A. M. Truscello. - 290:2(1996), pp. 117-123.

Fast atom bombardment mass spectrometry as a tool for the rapid determination of enantioselective binding of methylated cyclodextrins

TRUSCELLO, ADA
1996

Abstract

The first FABMS study of the enantioselectivity shown during complex formation between per-methylated cyclodextrins and pairs of enantiomeric guest molecules is described. The 1:1 mixtures of the cyclodextrins, both α- and β-, with the guests, the methyl esters of the amino acids tryptophan and phenylalanine, were studied in a 100:50:1 glycerol-thioglycerol-trifluoro-acetic acid matrix. The uncomplexed cyclodextrin peaks were then used as internal standards to determine the preference of the cavity for one or other of the enantiomers. A clear trend for the preferential binding, greater than 5:1 in each case, of the d-enantiomers of the amino acid esters was observed in agreement with literature 1H NMR experiments. This methodology provides a rapid route to assessing the enantioselectivity shown by the widely used cyclodextrins towards pairs of enantiomeric guests.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11311/660055
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