Reaction of lysine with aldoses

Giovanni Candiano, Gian Marco Ghiggeri, Gerolamo Delfino, Carlo Quierolo, Carla Cuniberti, Elisabetta Gianazza, Pier Giorgio Righetti

Research output: Contribution to journalArticle

Abstract

The reactivity of amino acids with trioses and hexoses under physiological conditions (37°, pH 7.5) has been investigated. The most reactive species were lysine, glyceraldehyde, and 2-amino-2-deoxyglucose. They generated yellow, oligomeric compounds having molecular weights in the range 500-1000 and pI values in the range pH 4-6. In the Lys-glyceraldehyde adduct, the ε-amino group is incorporated into a pyrrole-type structure, which gives a positive reaction with the Pauly reagent. The largest oligomers correspond to the condensation of 4 mol of Lys with 8-10 mol of glyceraldehyde. It is hypothesised that the primary Amadori-compound rearranges during the Maillard reaction to give browning products, since no yellow oligomers are produced if the Lys-aldehyde adduct is reduced immediately with cyanoborohydride.

Original languageEnglish
Pages (from-to)99-112
Number of pages14
JournalCarbohydrate Research
Volume145
Issue number1
DOIs
Publication statusPublished - Dec 15 1985

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

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    Candiano, G., Ghiggeri, G. M., Delfino, G., Quierolo, C., Cuniberti, C., Gianazza, E., & Righetti, P. G. (1985). Reaction of lysine with aldoses. Carbohydrate Research, 145(1), 99-112. https://doi.org/10.1016/S0008-6215(00)90416-6