title: Amino acid catalysis of 2-alkylfuran formation from lipid oxidation-derived α,β-unsaturated aldehydes.
abstract: The formation of 2-alkylfurans from the corresponding lipid-derived α,β-unsaturated aldehydes under dry-roasting conditions was investigated in detail. The addition of an amino acid to an α,β-unsaturated aldehyde drastically increased 2-alkylfuran formation. Peptides and proteins as well were able to catalyze 2-alkylfuran formation from the corresponding α,β-unsaturated aldehydes. Further investigation of 2-alkylfuran formation showed the need of oxidizing conditions and the involvement of radicals in the reaction. This way, the formation of 2-methylfuran from 2-pentenal, 2-ethylfuran from 2-hexenal, 2-propylfuran from 2-heptenal, 2-butylfuran from 2-octenal, 2-pentylfuran from 2-nonenal, and 2-hexylfuran from 2-decenal was shown. The impact of amino acids on 2-alkylfuran formation from lipid-derived α,β-unsaturated aldehydes represents an interesting example of the complex role of amino acids in the multitude of chemical reactions occurring during thermal processing of lipid-rich foods.
authors.affiliation: Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure links 653, B-9000 Ghent, Belgium.
authors.forename: An
authors.initials: A
authors.lastname: Adams
authors.forename: Capucine
authors.initials: C
authors.lastname: Bouckaert
authors.forename: Fien
authors.initials: F
authors.lastname: Van Lancker
authors.forename: Bruno
authors.initials: B
authors.lastname: De Meulenaer
authors.forename: Norbert
authors.initials: N
authors.lastname: De Kimpe
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D002384:Catalysis; D005663:Furans / Q000138:chemical synthesis*; D006358:Hot Temperature; D015227:Lipid Peroxidation
chemical_list: D000447:Aldehydes; D000596:Amino Acids; D005663:Furans