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Determination of Protonation Constants of O-Phospho-l-serine in Aqueous Solution: Potentiometry, Microcalorimetry, NMR Spectroscopy and Quantum Chemical Calculations

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Abstract

O-Phospho-l-serine is one of the naturally occurring phosphorylated amino acids, having important pharmacological activity and bioactivity. The protonation constants of O-phospho-l-serine were determined by means of potentiometric titrations at 25 °C and ionic strength of 0.5 mol·L−1 (NaCl). The heat effects of the protonation reaction of the O-phospho-l-serine were measured by direct calorimetry. NMR spectroscopy has demonstrated that the first protonation site occurs at the nitrogen atom in the amino group, followed by one of the oxygen atoms in the phosphono group, and finally the carboxyl oxygen atom. This trend is in good agreement with the enthalpy of protonation and quantum chemical calculations. These data will help to predict the speciation of O-phospho-l-serine in physiological systems.

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Acknowledgements

The authors thank the National Natural Science Foundation of China (Grant No. 41573122) and China Academy of Engineering Physics for financial support.

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Authors and Affiliations

  1. Institute of Nuclear Physics and Chemistry, China Academy of Engineering Physics, Mianyang, 621999, Sichuan, China

    Bijun Liu, Qianhong Yu, Qiang Li, Wanjun Mu, Zhaoyi Tan & Xingliang Li

  2. Southwestern Institute of Physics, Chengdu, 610041, Sichuan, China

    Yin Tian

  3. State Key Laboratory of Environmental Criteria and Risk Assessment, Chinese Research Academy of Environmental Sciences, Beijing, 100012, China

    Fengchang Wu

  4. Institute of High Energy Physics, Chinese Academy of Sciences, Beijing, 100049, China

    Dongqi Wang

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  1. Bijun Liu
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Liu, B., Tian, Y., Yu, Q. et al. Determination of Protonation Constants of O-Phospho-l-serine in Aqueous Solution: Potentiometry, Microcalorimetry, NMR Spectroscopy and Quantum Chemical Calculations. J Solution Chem 46, 2281–2292 (2017). https://doi.org/10.1007/s10953-017-0696-6

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