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Paper | Regular issue | Vol 104, No. 6, 2022, pp.1074-1084
Published online, 25th March, 2022
DOI: 10.3987/COM-22-14647
FAB-MS Measurement of 2-Hydroxyestrone and Monosaccharides Assisted by 4-Pyridineboronic Ester Derivatization

Sachiko Komatsu, Katsuhiko Sato,* Kyoko Sugiyama, Masayuki Kumano, Kazuhiro Watanabe,* and Tsutomu Fujimura

*Laboratory of Synthetic and Medicinal Chemistry, Department of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan


Phenylboronic acid (PBA) reacts specifically with diol compounds such as sugars. Compared with general derivatization, boronic ester derivatization has the advantage of being a simple procedure and requires fewer resources for sample pretreatment. To improve the detection sensitivity and selectivity for diol compounds in mass spectrometry, we investigated the effect of boronic ester derivatization of diol compounds on the detection sensitivity. As a result, several proton-affinitive boronic acids were examined, and the peak intensities of the ions associated with 2-hydroxyestrone were observed with 4-pyridineboronic acid as the reagent. The 4-pyridineboronic ester derivatization approach was found to be a useful labeling method for FAB-MS measurements due to the proton and diol affinity from the heterocyclic moiety.