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Studies on the Reaction of trans-2-heptenal With Peanut Proteins

Studies on the Reaction of trans-2-heptenal With Peanut Proteins

Martin Globisch, Marco Schindler, Jana Kreßler, Thomas Henle

J Agric Food Chem. 2014 Aug 20;62(33):8500-7.

PMID: 25065678

Abstract:

Hexanal, 2-heptenal, and nonanal were identified as relevant reaction products formed in the course of the lipid peroxidation of heated peanut oil. For the identification of potential amino acid side chain adducts, kinetic studies between N(α)-benzoylglycyl-l-lysine as a model for protein-bound lysine and trans-2-heptenal were performed, showing a strong decrease of the lysine-derivative whereupon the loss of trans-2-heptenal was moderate. Following acid hydrolysis of the incubation mixture of N(α)-acetyl-l-lysine and trans-2-heptenal, two UV-active major lipation products were observed, isolated and identified as isomeric pyridinium-derivatives, namely (Z)- and (E)-1-(5-amino-5-carboxypentyl)-4-butyl-3-(pent-1-en-1-yl)pyridin-1-ium (cis- and trans-BPP-lysine). After heating of a native peanut protein extract with trans-2-heptenal, both derivatives were quantitated by LC-ESI-MS/MS after acid hydrolysis and the modification of lysine was measured by amino acid analysis. At low, "food-relevant", concentrations of trans-2-heptenal, up to 80% of the lysine modification could be explained by the formation of cis- and trans-BPP-lysine, showing that these two lipation derivatives represent good markers for a protein modification by the lipid peroxidation product trans-2-heptenal.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP18829555	trans-2-Heptenal		18829-55-5	Price

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