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Simultaneous determination of all aminobutyric acids by chiral derivatization and liquid chromatography-tandem mass spectrometry

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Abstract

Aminobutyric acids include eight structural or stereoisomers that exhibit a wide range of biological activities. Recent evidence on some low abundant isomers have increased the demand for highly selective analysis of all the isomers; however, simultaneous separation of all the aminobutyric acid isomers has not been successful yet, except for a specialized method that uses multiple separation columns and a split of samples. In this study, we developed a new analytical method using chiral derivatization and liquid chromatography-tandem mass spectrometry to separate all the aminobutyric acid isomers in a single separation column. All the diastereomeric derivatives were resolved in a C18 column, and the derivatives showed characteristic fragmentation patterns in tandem mass spectrometry. By using the method, we analyzed the isomers in the Arabidopsis thaliana seeds and revealed the existence of three low abundant isomers, i.e., d-, l-β-aminoisobutyric acid, and d-β-aminobutyric acid. The proposed method uses a commercially available chiral derivatizing reagent and a broadly used column; therefore, it can be widely used in biological and food analyses.

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Data availability

The datasets obtained during the current study are available from the corresponding author on reasonable request.

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Acknowledgements

RIKEN Arabidopsis Col-0 seeds (SJA05800) used in the preliminary experiments were provided by RIKEN BRC, which is participating in the National BioResource Project of the MEXT/AMED, Japan. We thank Dr. Katsuhiro Nakanishi for his technical advice and constructive comments on the analysis of plant seeds. This work was supported by the Japan Society for the Promotion of Science (JSPS) KAKENHI under Grant numbers 20K15972 and 22K15264 (to E.S.).

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Authors and Affiliations

  1. Laboratory of Analytical and Bio-Analytical Chemistry, School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-Ku, Shizuoka, 422-8526, Japan

    Eiji Sugiyama, Mao Nakamura, Aogu Furusho & Kenichiro Todoroki

  2. Laboratory of Analytical Chemistry, Faculty of Pharmacy, Meijo University, 150 Yagotoyama, Tempaku, Nagoya, 468-8503, Japan

    Hajime Mizuno

Authors
  1. Eiji Sugiyama
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  2. Mao Nakamura
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  3. Hajime Mizuno
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  4. Aogu Furusho
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  5. Kenichiro Todoroki
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Contributions

ES: conceptualization, resources, methodology, visualization, investigation, writing—original draft preparation, project administration, and funding acquisition. MN: methodology, visualization, data curation, formal analysis, validation, writing—reviewing, and editing. HM: resources, writing—reviewing and editing, and funding acquisition. AF: resources, methodology, supervision, writing—reviewing and editing. KT: resources, writing—reviewing and editing, supervision, funding acquisition.

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Correspondence to Kenichiro Todoroki.

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Sugiyama, E., Nakamura, M., Mizuno, H. et al. Simultaneous determination of all aminobutyric acids by chiral derivatization and liquid chromatography-tandem mass spectrometry. ANAL. SCI. 39, 463–472 (2023). https://doi.org/10.1007/s44211-023-00293-w

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