Abstract
Defining chiral centres is addressed by introducing a pair of chiral auxiliary groups. Ions of diastereomeric pairs of molecules could be distinguished utilising energy-resolved mass spectrometry, and the applicability of the method to a series of compounds carrying amine, carboxylic acid, alcohol, and all the amino acids was verified. The method was further strengthened by distinguishing diastereomeric ions that did not undergo fragmentation. Mass spectrometric evaluation of the dissociation process of adducted sodium cations from the diastereomeric precursors agreed with the theoretical calculations, indicating the potential usefulness of the method for the determination of absolute configurations.
Highlights
With the aid of a chiral neutral gas, to differentiate the drift times of ionised chiral molecules[19]
In the course of our investigations to develop a new method for the analysis of glycan structures, we reported that the anomeric configurations of carbohydrates, which may be considered as examples of diastereomers, could be determined by ERMS29–31
The following were the important objectives of this study: (1) to confirm applicability of energy-resolved mass spectrometry (ERMS) method to a wide range of diastereomers derived from a pair of chiral compounds; (2) to distinguish a pair of isomeric ions derived from small molecules that do not produce fragment ions; and (3) to understand the principles underlying the discrimination
Summary
With the aid of a chiral neutral gas, to differentiate the drift times of ionised chiral molecules[19]. Despite its potential for the analysis of diastereomeric ions, the generality of this method has not been assessed Another problem with CID is that no information can be obtained about the precursor ion when the metal cation adduct dissociates before the breakdown of other constituent chemical bonds. The following were the important objectives of this study: (1) to confirm applicability of ERMS method to a wide range of diastereomers derived from a pair of chiral compounds; (2) to distinguish a pair of isomeric ions derived from small molecules that do not produce fragment ions; and (3) to understand the principles underlying the discrimination. The ERMS technique was able to discriminate between a series of diastereomeric molecular ion pairs containing chiral auxiliaries, which suggested that the method could be applied to a wide range of compounds. A theoretical basis was suggested to explain the phenomena
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