GC/EI-MS Analysis of Amino Acids Derivatized with Pentafluorobenzyl Bromide

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  • TANAKA Anna
    Graduate School of Life Sciences, Tokyo University of Pharmacy and Life Sciences
  • OCHIAI Haruka
    Graduate School of Life Sciences, Tokyo University of Pharmacy and Life Sciences
  • KUMATA Hidetoshi
    Department of Molecular Life Sciences, School of Life Sciences, Tokyo University of Pharmacy and Life Sciences
  • ENOMOTO Takeshi
    JEOL
  • UMEMURA Tomonari
    Department of Molecular Life Sciences, School of Life Sciences, Tokyo University of Pharmacy and Life Sciences

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Other Title
  • アミノ酸のペンタフルオロベンジル誘導体のGC/EI-MSによる解析
  • アミノサン ノ ペンタフルオロベンジル ユウドウタイ ノ GC/EI-MS ニ ヨル カイセキ

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Abstract

<p>The determination of amino acids by gas chromatography-mass spectrometry (GC-MS) using a one-step derivatization with pentafluorobenzyl bromide (PFB-Br) in an aqueous acetone phase is described. Although GC-MS analysis of amino acids by pentafluorobenzyl (PFB) derivatization has been reported previously, its application to non-proteinogenic free amino acids, which play important biological roles in various metabolic pathways, has not been reported. In this study, 6 non-proteinogenic amino acids (sarcosine, 2-aminobutyric acid, 3-aminoisobutyric acid, β-alanine, 2-aminoadipic acid, and cystine) as well as 19 proteinogenic amino acids, with the exception of arginine, were PFB derivatized and analyzed by GC-MS using both electron ionization (EI) and positive-ion chemical ionization (PICI) modes. Two derivative peaks were observed for each amino acid with primary amino groups, which were identified as di- and/or tri-substituted derivatives (i.e., NH(PFB)-CHR-COO(PFB) or N(PFB)2-CHR-COO(PFB)) based on their EI- and PICI-mass spectra. The ratio of the tri-substituted to the sum of the di- and tri-substituted derivative peaks was highest in glycine and β-alanine and lowest in branched amino acids, suggesting a dependence on steric hindrance around amino groups. Based on the identification of PFB derivative peaks, their retention indices on (5 % -phenyl)-methylpolysiloxane liquid phase capillary column, target and qualifier ions for selected ion monitoring (SIM) analysis on GC-EI-MS were determined to compile a quantification database.</p>

Journal

  • BUNSEKI KAGAKU

    BUNSEKI KAGAKU 72 (10.11), 407-416, 2023-10-05

    The Japan Society for Analytical Chemistry

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