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

20 Citations (Scopus)

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

Fingerprint

Glyceraldehyde
Lysine
Oligomers
Trioses
Maillard Reaction
Pyrroles
Hexoses
Glucosamine
Aldehydes
Condensation
Molecular Weight
Molecular weight
Amino Acids

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

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

Reaction of lysine with aldoses. / Candiano, Giovanni; Ghiggeri, Gian Marco; Delfino, Gerolamo; Quierolo, Carlo; Cuniberti, Carla; Gianazza, Elisabetta; Righetti, Pier Giorgio.

In: Carbohydrate Research, Vol. 145, No. 1, 15.12.1985, p. 99-112.

Research output: Contribution to journalArticle

Candiano, G, Ghiggeri, GM, Delfino, G, Quierolo, C, Cuniberti, C, Gianazza, E & Righetti, PG 1985, 'Reaction of lysine with aldoses', Carbohydrate Research, vol. 145, no. 1, pp. 99-112. https://doi.org/10.1016/S0008-6215(00)90416-6
Candiano G, Ghiggeri GM, Delfino G, Quierolo C, Cuniberti C, Gianazza E et al. Reaction of lysine with aldoses. Carbohydrate Research. 1985 Dec 15;145(1):99-112. https://doi.org/10.1016/S0008-6215(00)90416-6
Candiano, Giovanni ; Ghiggeri, Gian Marco ; Delfino, Gerolamo ; Quierolo, Carlo ; Cuniberti, Carla ; Gianazza, Elisabetta ; Righetti, Pier Giorgio. / Reaction of lysine with aldoses. In: Carbohydrate Research. 1985 ; Vol. 145, No. 1. pp. 99-112.
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