Anomeric configuration of hemiacetal has been regarded as less important in structural determination of oligosacharide, because hemiacetals isomerize to equilibrium in aqueous solvent. However, previous report indicated that hemiacetals hold the anomeric configurations of their precursor glycosides under collision-induced dissociation conditions in mass spectrometry. Consequently, structural investigation of hemiacetals in gas phase is considered to be valuable.     This study has addressed a possibility of discriminating anomers of sodiated hemiacetals obtained from corresponding glycosides, which proved to be possible. Although computational analysis indicates that ground-state energies between anomers of sodiated hemiacetals are different, confirmation of which has not been feasible. Our results show a possibility of predicting the anomeric configuration of a glycosidic linkage by computation.

Resolving anomers by mass spectrometry

243rd National Meeting (2012)

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