Maillard Reaction of Free and Nucleic Acid-Bound 2-Deoxy-D-ribose and D-Ribose with ω-Amino Acids

Georg T. Wondrak, Roland Tressl, Dieter Rewicki

Research output: Contribution to journalArticle

17 Scopus citations

Abstract

The Maillard reaction of free and nucleic acid-bound 2-deoxy-D-ribose and D-ribose with ω-amino acids (4-aminobutyric acid, 6-aminocaproic acid) was investigated under both stringent and mild conditions. Without (with) amines 2-deoxy-D-ribose (D-ribose) displays the strongest browning activity, and DNA is much more reactive than RNA. From stringent reaction between 2-deoxy-D-ribose (or DNA) and methyl 4-aminobutyrate, methyl 4-[2-[(oxopyrrolidinyl)methyl]-1-pyrrolyl]-butyrate (12) was identified by GC/MS and NMR as a new 2-deoxy-D-ribose specific key compound trapped by pyrrolidone formation. Levulinic acid-related N-substituted lactames 13-15 were identified as predominant products from DNA with amino acids, whereas RNA paralleled the reaction with D-ribose. α-Angelica lactone (2), a significant degradation product of DNA, and thiols leads under mild conditions to new addition products (e.g., 17 with glutathione). Probable reaction pathways considering activating effects of the polyphosphate backbone of nucleic acids are discussed.

Original languageEnglish (US)
Pages (from-to)321-327
Number of pages7
JournalJournal of Agricultural and Food Chemistry
Volume45
Issue number2
StatePublished - Feb 1 1997
Externally publishedYes

Keywords

  • Levulinic acid
  • Maillard reaction of nucleic acids / 2-deoxy-D-ribose
  • Pyrroles from ω-amino acids and riboses / nucleic acids
  • Trapping of 2-(hydroxymethyl)pyrrole
  • α-angelica lactone

ASJC Scopus subject areas

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

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