Mass Spectrometric Elucidation of Phenolic Oxidation Processes with Cu2+-Adduct

  • HAYASHI Akio
    School of Material Sciences, Japan Advanced Institute of Science and Technology
  • TANIGUCHI Noriko
    School of Material Sciences, Japan Advanced Institute of Science and Technology
  • TSUJIMOTO Kazuo
    School of Material Sciences, Japan Advanced Institute of Science and Technology
  • KUBO Isao
    Department of Environmental Science, Policy and Management, University of California

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  • Mass Spectrometric Elucidation of Phenolic Oxidation Processes with Cu〔2+〕-Adduct

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Abstract

Formation of ε complex with 2-hydroxy-6-[8′(Z),11′(Z),14′-pentadecatrienyl]benzoic acid (anacardic acid) and copper ion in the respective ratios of 2 : 1 and 1 : 1 at room temperature was observed by electrospray ionization mass spectrometry. The oxidation of 3-(3,4-dihydroxyphenyl)alanine (DOPA) in the presence of anacardic acid showed competitive inhibition with temporary reduction from dopaquinone to DOPA. In the oxidation of neurotensin, the oxidized products, dopaquinone-derivatives, were observed. Mass spectrometry revealed that the enzymatic oxidation of tyrosine residue is inhibited by anacardic acid.

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