Structure and potential cross-linking reactivity of a new pentose-specific Maillard product

Roland Tressl, Georg T Wondrak, Evelyn Kersten, Dieter Rewicki

Research output: Contribution to journalArticle

6 Citations (Scopus)

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 ω-(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 cross-linkers in Maillard reactions.

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

Fingerprint

Pentoses
Maillard Reaction
Arabinose
pentoses
crosslinking
gamma-Aminobutyric Acid
Lysine
Glyceraldehyde
Aminocaproic Acid
Ribose
Xylose
acids
Acetylcysteine
Maillard reaction
arabinose
Carboxylic Acids
Fructose
Sulfhydryl Compounds
Sugars
Labeling

Keywords

  • ω-(3,4-dimethyl-2,5-dioxo-2,5-dihydropyrrol-1-yl)carboxylic acids, formation from pentoses
  • Maillard reaction, new pentose-specific product with ω-amino acids
  • N-(dimethylmaleoyl)-ω-amino acids, formation in Maillard reactions

ASJC Scopus subject areas

  • Agricultural and Biological Sciences (miscellaneous)
  • Food Science
  • Chemistry (miscellaneous)

Cite this

Structure and potential cross-linking reactivity of a new pentose-specific Maillard product. / Tressl, Roland; Wondrak, Georg T; Kersten, Evelyn; Rewicki, Dieter.

In: Journal of Agricultural and Food Chemistry, Vol. 42, No. 12, 1994, p. 2692-2697.

Research output: Contribution to journalArticle

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