Glycosylation of lysine-containing pentapeptides by glucuronic acid: new insights into the Maillard reaction

Horvat, Štefica; Roščić, Maja

doi:10.1016/j.carres.2009.11.031

Cited by 13 publications

(7 citation statements)

References 26 publications

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“…Glucuronic acid is another monosaccharide with importance in phase II of metabolism implicated in the detoxification of drugs that has been described to generate Amadori adducts under non-enzymatic conditions, and it has been conjugated to lysine containing pentapeptides under mild conditions [31] (Figure 17). As predicted, amino purines also react with glucose either in the open or cyclic forms leading through the imine of Schiff product which establish an equilibrium with the enaminol product, and then addition to the enamine to form the cyclic Amadori-purine, adducts [31][32][33] (Figure 18).…”

Section: Annals Of Reviews and Researchmentioning

confidence: 99%

The Chemistry of Oxidative Stress and Glycoxidation As Risk Factors for Developing Degenerative Disease

Brito Arias

2019

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Oxidative stress conceived as an abnormal production of highly reactive oxygen species has been strongly implicated in degenerative and chronic diseases such as diabetes, cancer, coronary artery disease, vitiligo, arteriosclerosis, lupus, rheumatoid arthritis, and neurodegenerative pathologies. Additionally, glycoxidation is intimately associated with diabetes, coronary heart disease, retinopathy, Parkinson, Lewy body disease and aging. These oxidative processes are strongly interconnected and related to common alterations and therefore it is primordial to understand their chemistry and what is the impact of the oxidative stress and glycoxidation on the modulation and homeostasis of the body, with the aim of establishing strategies that could lead to the prevention or control of chronic and degenerative disease.

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Section: Annals Of Reviews and Researchmentioning

confidence: 99%

The Chemistry of Oxidative Stress and Glycoxidation As Risk Factors for Developing Degenerative Disease

Brito Arias

2019

ARR

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“…Recently, structurally more simple pyridinium compounds have been detected from the reaction between several lysine-containing pentapeptides and glucuronic acid 99 under dry heating conditions (50 °C; RH 75%; 5 days) . It was shown that the Amadori product was formed in the initial phase of the reaction and decreased later on, whereas the formation of the pyridinium derivatives increased linearly after an initial lag phase, suggesting the Amadori compound as their precursor.…”

Section: Reactions Of Peptides With Carbonyl Compoundsmentioning

confidence: 99%

“…It was shown that the Amadori product was formed in the initial phase of the reaction and decreased later on, whereas the formation of the pyridinium derivatives increased linearly after an initial lag phase, suggesting the Amadori compound as their precursor. A mechanism for the formation of these pyridinium derivatives has been proposed (Scheme ).…”

Section: Reactions Of Peptides With Carbonyl Compoundsmentioning

confidence: 99%

Chemical Modifications of Peptides and Their Impact on Food Properties

2011

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Introduction 7876 2. Importance of Peptides in Food 7877 3. Degradation of Peptides without the Intervention of Other Reactive Species 7877 3.1. Peptide Chain Cleavage 7879 3.1.1. Peptide Hydrolysis 7879 3.1.2. Intramolecular Cyclizations in the Peptide Chain 7879 3.2. Peptide Backbone Modifications 7881 3.3. Peptide Side-Chain Modifications 7882 3.4. Peptide Cross-Linking 7883 3.5. Peptide Breakdown 7884 4. Reactions of Peptides with Carbonyl Compounds 7885 4.1. Reactions between Peptides and Carbohydrates 7885 4.1.1. Introduction 7885 4.1.2. Initial Stage of the Maillard Reaction 7885 4.1.3. Advanced Stages of the Maillard Reaction 7887 4.1.3.1. Formation of Color 7888 4.1.3.2. Formation of Taste 7888 4.1.3.3. Formation of Aroma 7888 4.1.3.4. Formation of Biological Activity 7889 4.1.3.5. Formation of Peptide Side-Chain Modifications and Cross-Links 7890 4.2. Reactions between Peptides and Lipids 7893 4.3. Reactions between Peptides and Glyoxal or Methylglyoxal 7896 4.4.

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“…The Maillard reaction is a non-enzymatic browning reaction between amino-containing compounds and carbonyl compounds [8]. It plays a crucial role in food processing and storage and generates a wide range of Maillard reaction products (MRPs) [9].…”

Section: Introductionmentioning

confidence: 99%

Contribution of Lipids to the Flavor of Mussel (Mytilus edulis) Maillard Reaction Products

Xin

Liu

et al. 2022

Foods

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Lipid oxidation and the Maillard reaction are two of the most important reactions affecting the flavor of foods that have been heat-processed. To investigate the contribution of lipids to the mussel’s flavor, the mussel’s Maillard reaction products (MRPs) were prepared with polar lipids (mainly phospholipids) and nonpolar lipids (mainly glycerides), respectively. The effects of polar and nonpolar lipids on the flavor of the MRPs were investigated by sensory evaluation, electronic tongue, electronic nose, ultra-performance liquid chromatography-mass-spectrometry (UPLC-MS) and gas chromatography-mass-spectrometry (GC-MS). From the sensory evaluation results, the polar lipid MRPs had the highest scores. The tastes of polar lipid MRPs and nonpolar lipid MRPs were mainly umami, saltiness and sourness, and there were significant differences in their sour tastes. The flavor compounds in the MRPs were mainly inorganic sulfides, organic sulfides and nitrogen oxides. The odor of polar lipid MRPs was stronger than that of nonpolar lipid MRPs, and the seafood flavor was more obvious. A total of 37 volatile compounds were detected by GC-MS, mainly aldehydes, alcohols and ketones. The addition of polar lipids helped the MRPs to produce more volatile compounds. A total of 177 non-volatile compounds (including amino acids and their derivatives and oligopeptides, etc.) were detected in the samples using UPLC-MS. The non-volatile compounds contained in the no-lipid MRPs, polar lipid MRPs and nonpolar lipid MRPs were significantly different. This study provides a theoretical basis and technical support for the production of mussel MRPs.

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Glycosylation of lysine-containing pentapeptides by glucuronic acid: new insights into the Maillard reaction

Cited by 13 publications

References 26 publications

The Chemistry of Oxidative Stress and Glycoxidation As Risk Factors for Developing Degenerative Disease

The Chemistry of Oxidative Stress and Glycoxidation As Risk Factors for Developing Degenerative Disease

Chemical Modifications of Peptides and Their Impact on Food Properties

Contribution of Lipids to the Flavor of Mussel (Mytilus edulis) Maillard Reaction Products

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