Relative acidity scale of glycine- and taurine-conjugated bile acids through ESI-MS measurements

The most important bile acids, in the form of glycine and taurine conjugates, have been ordered in terms of relative acidity scale. The measurements have been carried out using mass spectrometric techniques. The group of taurine conjugates confirm the superior acidity over the glycine derivatives. Rationale of the differences found in gas-phase and comparison with the data reported in solution-phase are discussed with the support of theoretical calculations. The study has been completed with the acidity sequence of mixed oxo-hydroxy bile acids.

► Mass spectrometry enables relative proton affinity measurements in gas-phase. ► Acidity of the most abundant mammalian bile acids as glycine and taurine conjugates. ► The role of specific hydroxy functions, able to intramolecular hydrogen bond.