N-(1-Deoxy- d -xylulos-1-yl)-glutathione: A Maillard Reaction Intermediate Predominating in Aqueous Glutathione-Xylose Systems by Simultaneous Dehydration-Reaction

Wei Tang, Heping Cui, Fuli Sun, Xiaohong Yu, Khizar Hayat, Shahzad Hussain, Muhammad Usman Tahir, Xiaoming Zhang, Chi Tang Ho

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Abstract

The effect of simultaneous dehydration-reaction (SDR) on Amadori rearrangement product (ARP) N-(1-deoxy-d-xylulos-1-yl)-glutathione and its key degradation products, 3-deoxyxylosone (3-DX) and 1-deoxyxylosone (1-DX), were investigated in an aqueous glutathione-xylose (GSH-Xyl) system. The yield of ARP was increased to 67.98% by SDR compared with 8.44% by atmospheric thermal reaction at 80 °C. Reaction kinetics was applied to analyze the mechanism and characteristics of ARP formation and degradation under SDR. ARP formation and degradation rate was highly dependent on temperature, and the latter was more sensitive to temperature. By regulating the reaction conditions of temperature and pH, the ratio of ARP formation rate constant to its degradation rate constant could be controlled to achieve an efficient preparation of ARP from GSH-Xyl Maillard reaction through SDR.

Original languageEnglish (US)
Pages (from-to)8994-9001
Number of pages8
JournalJournal of agricultural and food chemistry
Volume67
Issue number32
DOIs
StatePublished - Aug 14 2019

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All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Agricultural and Biological Sciences(all)

Keywords

  • N-(1-deoxy- d -xylulos-1-yl)-glutathione
  • deoxyxylosones
  • peptide Maillard reaction
  • reaction kinetics
  • simultaneous dehydration-reaction

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