Structure and Potential Cross‐linking Reactivity of a New Pentose-Specific Maillard Product

Roland Tressl, Georg Wondrak, Evelyn Kersten, Dieter Rewicki

Research output: Contribution to journalArticle

7 Scopus citations

Abstract

The Maillard reaction of model compounds for peptide-bound lysine (4-aminobutyric acid, 6-aminocaproic acid, Nα-acetyl-l-lysine) with reducing sugars (d-ribose, d-xylose, d-arabinose, d-glucose, d-fructose, d-glyceraldehyde) was investigated under both stringent and mild conditions. With pentoses the corresponding co-(dimethylmaleimido)carboxylic acids 1‐3 were identified as substantial, hitherto unknown components by GC/MS and NMR. Their structure was confirmed by synthesis. A pathway to compounds 1‐3 was derived from the results of 4-aminobutyric acid/[1-13C]-d-arabinose isotopic labeling experiments. The new N-(dimethylmaleoyl)-ω-aminocarboxylic acid derivatives are shown to react under very mild conditions (pH 7, 32 °C) with thiols (methyl 3-mercaptopropionate, Nα-acetyl-l-cysteine methyl ester) to form the addition products 4-6. This reaction demonstrates that compounds of type 1-3 can be considered as potential protein crosslinkers in Maillard reactions.

Original languageEnglish (US)
Pages (from-to)2692-2697
Number of pages6
JournalJournal of Agricultural and Food Chemistry
Volume42
Issue number12
DOIs
StatePublished - Dec 1 1994
Externally publishedYes

Keywords

  • Maillard reaction
  • Maillard reaction with 4-aminobutyricacid
  • Maillard reaction with co-amino acids
  • N-(dimethylmaleoyl)-ω-amino acids
  • N-(dimethylmaleoyl)-ω-amino acids
  • [l-C]-D-arabinose
  • formation from pentoses
  • formation in Maillard reactions
  • new pentose-specific product with ω-amino acids
  • pentoses
  • potential protein cross-linking reaction with SH groups
  • ω-(3,4-dimethyl-2,5-dioxo-2,5-dihydropyrroll-yl)carhoxylic acids

ASJC Scopus subject areas

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

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