Pyridinium-carbaldehyde: active Maillard reaction product from the reaction of hexoses with lysine residues

Carbohydr Res. 2004 Feb 25;339(3):705-14. doi: 10.1016/j.carres.2003.12.009.

Abstract

Besides the formation of the aminotriazine N6-[4-(3-amino-1,2,4-triazin-5-yl)-2,3-dihydroxybutyl]-L-lysine, the reaction of [1-13C]D-glucose with lysine and aminoguanidine leads to the generation of 6-[2-([[amino(imino)methyl]hydrazono]methyl)pyridinium-1-yl]-L-norleucine (14-13C1). The dideoxyosone N6-(2,3-dihydroxy-5,6-dioxohexyl)-L-lysine was shown to be a precursor in the formation of 14-13C1, which proceeds via the reactive carbonyl intermediate 6-(2-formylpyridinium-1-yl)-L-norleucine (13-13C1). In order to study the reactivity of 13-13C1, the model compound 1-butyl-2-formylpyridinium (18) was prepared in a two-step procedure starting from 2-pyridinemethanol. The reaction of the pyridinium-carbaldehyde 18 with L-lysine yielded the Strecker analogous degradation product 2-(aminomethyl)-1-butylpyridinium and another compound, which was shown to be as 1-butyl-2-[(2-oxopiperidin-3-ylidene)methyl]pyridinium. Reaction of 18 with the C-H acidic 4-hydroxy-5-methylfuran-3(2H)-one leads to the formation of the condensation product 1-butyl-2-[hydroxy-(4-hydroxy-5-methyl-3-oxofuran-2(3H)-ylidene)methyl]-pyridinium.

MeSH terms

  • Aldehydes / chemical synthesis*
  • Aldehydes / chemistry
  • Carbon Isotopes
  • Hexoses / chemistry*
  • Isotope Labeling
  • Lysine / chemistry*
  • Magnetic Resonance Spectroscopy
  • Maillard Reaction*
  • Molecular Structure
  • Pyridinium Compounds / chemical synthesis*
  • Pyridinium Compounds / chemistry

Substances

  • Aldehydes
  • Carbon Isotopes
  • Hexoses
  • Pyridinium Compounds
  • Lysine