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• W2058554199 endingPage "431" @default.
• W2058554199 startingPage "421" @default.
• W2058554199 abstract "Reactions between biological amines and reducing sugars (the Maillard reaction) are among the most important of the chemical and oxidative changes occurring in biological systems that contribute to the formation of a complex family of rearranged and dehydrated covalent adducts that have been implicated in the pathogenesis of human diseases. In this study, chemistry of the Maillard reactions was studied in four model systems containing fructosamines (Amadori compounds) obtained from the endogenous opioid pentapeptide leucine-enkephalin (Tyr-Gly-Gly-Phe-Leu), leucine-enkephalin methyl ester, structurally related tripeptide (Tyr-Gly-Gly), or from amino acid (Tyr). The degradation of model compounds as well as their ability to develop Maillard fluorescence was investigated under oxidative conditions in methanol and phosphate buffer pH 7.4 at two different temperatures (37 and 70 degrees C). At 37 degrees C, glycated leucine-enkephalin degraded slowly in methanol (t(1/2) approximately 13 days) and phosphate buffer (t(1/2) approximately 9 days), producing a parent peptide compound as a major product throughout a three-week incubation period. Whereas fluorescence slowly increased over time at 37 degrees C, incubations off all studied Amadori compounds at 70 degrees C resulted in a rapid appearance of a brown color and sharp increase in AGE (advanced glycation end products)-associated fluorescence (excitation 320 nm/emmision 420 nm) as well as in distinctly higher amounts of fragmentation products. The obtained data indicated that the shorter the peptide chain the more degradation products were formed. These studies have also helped to identify a new chemical transformation of the peptide backbone in the Maillard reaction that lead to beta-scission of N-terminal tyrosine side chain and p-hydroxybenzaldehyde formation under both aqueous and nonaqueous conditions." @default.
• W2058554199 created "2016-06-24" @default.
• W2058554199 creator A5054080757 @default.
• W2058554199 creator A5063473946 @default.
• W2058554199 date "2003-06-11" @default.
• W2058554199 modified "2023-10-15" @default.
• W2058554199 title "Study of degradation pathways of Amadori compounds obtained by glycation of opioid pentapeptide and related smaller fragments: Stability, reactions, and spectroscopic properties" @default.
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• W2058554199 doi "https://doi.org/10.1002/bip.10338" @default.
• W2058554199 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/12879488" @default.
• W2058554199 hasPublicationYear "2003" @default.
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