Kinetic and molecular orbital analyses of dicarboxylic acylcarnitine methylesterification show that derivatization may affect the screening of newborns by tandem mass spectrometry

Yasuhiro Maeda, Yoko Nakajima, Kana Gotoh, Yuji Hotta, Tomoya Kataoka, Naruji Sugiyama, Naohiro Shirai, Tetsuya Ito, Kazunori Kimura

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Newborns are routinely screened for organic acidemias by acylcarnitine analysis. We previously reported the partial catalytic methylesterification of dicarboxylic acylcarnitines by benzenesulfonic acid moiety in the solid extraction cartridge during extraction from serum. Since the diagnosis of organic acidemias by tandem mass spectrometry is affected by the higher molecular weight of these derivatized acylcarnitines, we investigated the methylesterification conditions. The kinetic constants for the methylesterification of carboxyl groups on the acyl and carnitine sides of carnitine were 2.5 and 0.24 h-1, respectively. The physical basis underlying this difference in methylesterification rates was clarified theoretically, illustrating that methylesterification during extraction proceeds easily and must be prevented.

Original languageEnglish
Pages (from-to)121-125
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume26
Issue number1
DOIs
Publication statusPublished - 01-01-2016

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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