Electrospray Ionisation Mass Spectrometry (ESI-MS): a powerful tool for the evaluation of chiral recognition in host-guest complexation

Abstract

The chiral recognition properties of a series of synthetic crown ethers or cryptands (1-10) incorporating a chiral spiroacetal moiety in the polyether chain toward ammonium enantiomeric pairs (G1 or G2) have been evaluated by Electrospray Ionisation Mass Spectrometry (ESI-MS). Isotopic-labelling has been used to distinguish one diastereomeric host-guest complex ion from the other. The reliability of this method has also been tested by studying the stability of the labelling and the influence of the labelling on the degree of chiral recognition. Various degrees of chiral recognition have emerged from this study.