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

✍ Scribed by Simon N. Davey; David A. Leigh; John P. Smart; Lee W. Tetler; Ada M. Truscello

• Publisher: Elsevier Science
• Year: 1996
• Tongue: English
• Weight: 332 KB
• Volume: 290
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(96)00145-0

✦ Synopsis

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:I mixtures of the cyclodextrins, both a-and fl-, with the guests, the methyl esters of the amino acids tryptophan and phenylalanine, were studied in a 100:50:1 glycerol-thioglycerol-trifluoroacetic 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 I H NMR experiments. This methodology provides a rapid route to assessing the enantioselectivity shown by the widely used cyclodextrins towards pairs of enantiomeric guests.