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Chiral Metabolomics Using Triazine-Based Chiral Labeling Reagents by UPLC-ESI-MS/MS

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Chiral Separations

Part of the book series: Methods in Molecular Biology ((MIMB,volume 1985))

Abstract

The determination of enantiomers of biological molecules is an important issue because a significant difference in the activity of the enantiomers is generally observed in biological systems. Chiral separations can be carried out by direct resolution using a chiral stationary column or by indirect resolution based on the derivatization with a chiral reagent. Many chiral-labeling reagents for ultraviolet-visible and fluorescence detections have been developed for various functional groups, such as amine and carboxylic acid. However, there are hardly any labeling reagents for LC-MS-specific detection. Based on this observation, we have developed several chiral-labeling reagents for LC-MS/MS analysis.

This chapter describes methodologies and applications for the indirect LC-MS/MS determination of biological chiral molecules using triazine-based chiral-labeling reagents, i.e., (S and R)-1-(4,6-dimethoxy-1,3,5-triazin-2-yl)pyrrolidin-3-amine (DMT-3(S and R)-Apy) for carboxylic acids and (S and R)-2,5-dioxopyrrolidin-1-yl-1-(4,6-dimethoxy-1,3,5-triazin-2-yl)pyrrolidine-2-carboxylate (DMT-(S and R)-Pro-OSu) for amines and amino acids. A reliable method for the non-targeted chiral metabolomics is also described in this chapter.

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Authors and Affiliations

  1. Laboratory of Analytical and Bio-Analytical Chemistry, Graduate School of Pharmaceutical Sciences, University of Shizuoka, Shizuoka, Japan

    Toshimasa Toyo’oka

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  1. Toshimasa Toyo’oka
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Correspondence to Toshimasa Toyo’oka .

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Editors and Affiliations

  1. Department of Pharmaceutical Chemistry, University of Jena, Jena, Germany

    Gerhard K. E. Scriba

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Toyo’oka, T. (2019). Chiral Metabolomics Using Triazine-Based Chiral Labeling Reagents by UPLC-ESI-MS/MS. In: Scriba, G.K.E. (eds) Chiral Separations. Methods in Molecular Biology, vol 1985. Humana, New York, NY. https://doi.org/10.1007/978-1-4939-9438-0_4

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  • DOI: https://doi.org/10.1007/978-1-4939-9438-0_4

  • Publisher Name: Humana, New York, NY

  • Print ISBN: 978-1-4939-9437-3

  • Online ISBN: 978-1-4939-9438-0

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