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Chemical activation of piperidine by formaldehyde and formation of lysine-specific Maillard reaction products

Piperidine is considered as a lysine-specific Maillard reaction product that can be formed from free lysine through decarboxylation and deamination reactions or through cyclization of pent-4-en-1-amine, the counterpart of acrylamide from lysine. Due to the importance and reactivity of piperidine its further interaction products in glucose/lysine model system was investigated. A useful strategy based on Py-GC/MS analysis was developed using an isotope labelling technique to identify reaction products incorporating piperidine moieties. Products simultaneously possessing five lysine carbon atoms (C2′–C6′) and the N&z.epsiv;-amino group from lysine in addition to glucose carbon atoms were targeted using specifically labelled precursors such as ( 15 Nα)Lysine·2HCl, ( 15 N&z.epsiv;)Lysine·2HCl, (U- 13 C 6 )Lysine·2HCl, ( 13 C-6)Lysine·2HCl and (U- 13 C 6 )Glucose. Detailed labelling studies using specifically 13 C-enriched sugars have shown that the piperidine can form reactive 1-methylidenepiperidinium ion with formaldehyde, which is able to undergo further aldol addition reactions to form compounds, such as 3-(piperidin-1-yl)propanal and 3-(pyridin-1(4 H )-yl)propanal. Furthermore, these studies have also demonstrated that oxidation of piperidine into di- and tetrahydropyridine derivatives can generate reactive eneamine moieties capable of nucleophilic attack at carbonyl groups and formation of pyridine derivatives. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Food Chemistry Elsevier
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