“Thermal Peroxidation” of Dietary Pentapeptides Yields N-Terminal 1,2-Dicarbonyls
Keyword(s):
In this contribution we investigate the thermal degradation of dietary-relevant pentapeptides. Most unsaturated lipids degrade by the well-known peroxidation mechanism. Here we show a degradation mechanism of peptides analogous to lipid peroxidation, forming a series of novel degradation products with possible toxicological relevance. At elevated temperatures above 180°C, pentapeptides with an N-terminal phenylalanine moiety react via a debenzylation to form 1,2-dicabonyl compounds, replacing the N-terminal primary amine. We propose a radical-based reaction mechanism that leads via a common peroxoaminal intermediate to two distinct types of reaction products with a terminal α-1,2 diamide or an α-amide-aldehyde functionality.
1982 ◽
Vol 60
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pp. 1207-1213
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1984 ◽
Vol 9
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pp. 209-224
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2002 ◽
Vol 952
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pp. 205-213
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2020 ◽
Vol 234
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pp. 708-720
2000 ◽
Vol 65
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pp. 867-875
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