Reaction of ascorbate with lysine and protein under autoxidizing conditions: formation of N epsilon-(carboxymethyl)lysine by reaction between lysine and products of autoxidation of ascorbate.

No abstract is available for this paper.

• Publication year

  1990

• Venue

  Biochemistry

• Publication date

  1990-12-11

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1021/BI00501A014PMID 2125497
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Glycation of lens proteins by the oxidation products of ascorbic acid.

  1990cited by this paper
• Implication of lysine residues in the loss of enzymatic activity in rat liver 6-phosphogluconate dehydrogenase found in aging.

  1989cited by this paper
• Conversion of amino acid residues in proteins and amino acid homopolymers to carbonyl derivatives by metal-catalyzed oxidation reactions.

  1989cited by this paper
• Oxidation of glycated proteins: age-dependent accumulation of N epsilon-(carboxymethyl)lysine in lens proteins.

  1989cited by this paper
• Non-enzymatic glycosylation.

  1989cited by this paper
• Deficiency of Ascorbic Acid in Experimental Diabetes: Relationship With Collagen and Polyol Pathway Abnormalities

  1988cited by this paper
• Aldehydes and dicarbonyls in non-enzymic glycosylation of proteins.

  1988cited by this paper
• Protein modification in aging.

  1988cited by this paper
• Oxidative degradation of glucose adducts to protein. Formation of 3-(N epsilon-lysino)-lactic acid from model compounds and glycated proteins.

  1988cited by this paper
• Ascorbic acid-induced crosslinking of lens proteins: evidence supporting a Maillard reaction.

  1988cited by this paper
• Hydroxyl radical production and autoxidative glycosylation. Glucose autoxidation as the cause of protein damage in the experimental glycation model of diabetes mellitus and ageing.

  1988cited by this paper
• The possible contribution of glucose autoxidation to protein modification of diabetes.

  1988cited by this paper
• The precipitation and cross-linking of lens crystallins by ascorbic acid.

  1988cited by this paper
• Advanced products of nonenzymatic glycosylation and the pathogenesis of diabetic vascular disease.

  1988cited by this paper
• Advanced glycosylation end products in tissue and the biochemical basis of diabetic complications.

  1988cited by this paper
• Glucose autoxidation and protein modification. The potential role of 'autoxidative glycosylation' in diabetes.

  1987cited by this paper
• In vitro oxidation of ascorbic acid and its prevention by GSH.

  1987cited by this paper
• Vitamin C metabolites and microangiopathy in diabetes mellitus.

  1987cited by this paper
• Identification of N epsilon-carboxymethyllysine as a degradation product of fructoselysine in glycated protein.

  1986cited by this paper
• The antioxidant role of vitamin C

  1986cited by this paper
• The role of ascorbic acid in senile cataract.

  1985cited by this paper
• Monosaccharide autoxidation in health and disease.

  1985cited by this paper
• The determination of dehydroascorbic acid and ascorbic acid in the serum and synovial fluid of patients with rheumatoid arthritis (RA).

  1985cited by this paper
• Glycation of amino groups in protein. Studies on the specificity of modification of RNase by glucose.

  1985cited by this paper
• Ascorbic acid metabolism in diabetes mellitus.

  1981cited by this paper
• Estimation of dehydroascorbic acid in blood of diabetic patients.

  1979cited by this paper
• N-EPSILON-(CARBOXYMETHYL)LYSINE, A CONSTITUENT OF HUMAN URINE.

  1975cited by this paper
• Nϵ-(carboxymethyd)lysine, a constituent of human urine

  1975cited by this paper
• Determination of amino acid profiles in biological samples by gas chromatography.

  1974cited by this paper
• The gas chromatographic determination of ascorbic acid in the form of its trimethylsilyl ether derivative.

  1967cited by this paper
• The distribution and possible functions of ascorbic acid in the eye

  1962cited by this paper
• Dehydrated Foods, Chemistry of Browning Reactions in Model Systems

  1953cited by this paper

• Inhibition and Promotion of Heat-Induced Protein Modifications in Whey by Vitamins: Quantitative Profiling of 14 Modifications at 29 β-Lactoglobulin Binding Sites.

  2025cites this paper
• Simultaneously Monitoring and Reducing Nε-Carboxymethyl-Lysine and 5-Hydroxymethylfurfural Contents During Soy Sauce Production and Consumption

  2025cites this paper
• Determination of glycation biomarkers in human fingernails by isotope-dilution liquid chromatography tandem mass spectrometry (LC-MS/MS).

  2024cites this paper
• Advanced Glycation End Products: A Comprehensive Review of Their Detection and Occurrence in Food

  2023cites this paper
• Autoxidation of ascorbate mediates lysine N-pyrrolation

  2022cites this paper
• Histone functions as a cell-surface receptor for AGEs

  2022cites this paper
• Dietary advanced glycation end-products, 2-monochloropropane-1,3-diol esters and 3-monochloropropane-1,2-diol esters and glycidyl esters in infant formulas: Occurrence, formulation and processing effects, mitigation strategies.

  2021cites this paper
• Application of nano/microencapsulated ingredients in milk and dairy products

  2021cites this paper
• Vitamin C is a source of oxoaldehyde and glycative stress in age‐related cataract and neurodegenerative diseases

  2020cites this paper
• Protein Glycation in Plants—An Under-Researched Field with Much Still to Discover

  2020cites this paper
• Dicarbonyls Generation, Toxicities, Detoxifications and Potential roles in Diabetes Complications.

  2020cites this paper
• Evaluation of the effect of berry extracts on carboxymethyllysine and lysine in ultra-high temperature treated milk.

  2020cites this paper
• Dynamics of Non-Canonical Amino Acid-Labeled Intra- and Extracellular Proteins in the Developing Mouse

  2019cites this paper
• Reduction of Nε-(carboxymethyl) lysine by (-)-epicatechin and (-)-epigallocatechin gallate: The involvement of a possible trapping mechanism by catechin quinones.

  2018cites this paper
• Kinetic investigation of the trapping of Nε-(carboxymethyl)lysine by 4-methylbenzoquinone: A new mechanism to control Nε-(carboxymethyl)lysine levels in foods.

  2018cites this paper
• Autoschizis: A Mode of Cell Death of Cancer Cells Induced by a Prooxidant TreatmentIn VitroandIn Vivo

  2018cites this paper
• Formation of Nε-carboxymethyllysine and Nε-carboxyethyllysine in ground beef during heating as affected by fat, nitrite and erythorbate

  2017cites this paper
• Dicarbonyls and Advanced Glycation End-Products in the Development of Diabetic Complications and Targets for Intervention

  2017influential citation
• Development and applications of molecularly imprinted polymers based on hydrophobic CdSe/ZnS quantum dots for optosensing of N(ε)-carboxymethyllysine in foods.

  2016cites this paper
• Encapsulation of ascorbic acid promotes the reduction of Maillard reaction products in UHT milk.

  2016cites this paper
• Identification of C1q as a Binding Protein for Advanced Glycation End Products.

  2016cites this paper
• The Role of Oxidative Stress in Diabetic Neuropathy: Generation of Free Radical Species in the Glycation Reaction and Gene Polymorphisms Encoding Antioxidant Enzymes to Genetic Susceptibility to Diabetic Neuropathy in Population of Type I Diabetic Patients

  2015cites this paper
• New tools in modulating Maillard reaction from model systems to food

  2015cites this paper
• Comprehensive analysis of maillard protein modifications in human lenses: effect of age and cataract.

  2015cites this paper
• Accumulation of modified proteins and aggregate formation in aging.

  2014cites this paper
• 28. Potential of the FAST index to characterize infant formula quality

  2014cites this paper
• N ϵ-(carboxymethyl)lysine: A Review on Analytical Methods, Formation, and Occurrence in Processed Food, and Health Impact

  2014influential citation
• Study of an Unusual Advanced Glycation End-Product (AGE) Derived from Glyoxal Using Mass Spectrometry

  2014cites this paper
• Investigations on the Maillard reaction of dextrins during aging of Pilsner type beer.

  2014cites this paper
• Reprint of "accumulation of modified proteins and aggregate formation in aging".

  2014cites this paper
• sugars, and lysine during the dairy thermal process

  2013cites this paper
• Simultaneous analysis of Nε-(carboxymethyl)lysine, reducing sugars, and lysine during the dairy thermal process.

  2013cites this paper
• Molecular strategies to prevent, inhibit, and degrade advanced glycoxidation and advanced lipoxidation end products

  2013cites this paper
• 6LPXOWDQHRXVDQDO\VLVRI10FDUER(\PHWK\OO\VLQHUHGXFLQJ sugars, and lysine during the dairy thermal process

  2013cites this paper
• Multispecificity of Immunoglobulin M Antibodies Raised against Advanced Glycation End Products

  2013cites this paper
• Reactants encapsulation and Maillard Reaction

  2013cites this paper
• Skin beautification with oral non-hydrolized versions of carnosine and carcinine: Effective therapeutic management and cosmetic skincare solutions against oxidative glycation and free-radical production as a causal mechanism of diabetic complications and skin aging

  2012cites this paper
• The LEGSKO Mouse: A Mouse Model of Age-Related Nuclear Cataract Based on Genetic Suppression of Lens Glutathione Synthesis

  2012cites this paper
• Formation and Inhibition of Nε-(Carboxymethyl)lysine in Saccharide-Lysine Model Systems during Microwave Heating

  2012cites this paper
• Vitamin C Degradation Products and Pathways in the Human Lens*

  2011cites this paper
• Naturally occurring inhibitors against the formation of advanced glycation end-products.

  2011cites this paper
• Genetic Determinants of Serum Ascorbic Acid Concentrations

  2011cites this paper
• The FAST index – A highly sensitive indicator of the heat impact on infant formula model

  2011cites this paper
• Cell Damage and Death by Autoschizis in Human Bladder (RT4) Carcinoma Cells Resulting from Treatment with Ascorbate and Menadione

  2010cites this paper
• The effects of grape seed extract fortification on the antioxidant activity and quality attributes of bread

  2010cites this paper
• Zur Wirkung von Phospholipiden in der thermisch induzierten Lipidperoxidation

  2010cites this paper
• Beneficial effects of cinnamon proanthocyanidins on the formation of specific advanced glycation endproducts and methylglyoxal-induced impairment on glucose consumption.

  2010cites this paper
• The health and technological implications of a better control of neoformed contaminants by the food industry.

  2010cites this paper
• Advanced glycation end products as biomarkers and gerontotoxins - A basis to explore methylglyoxal-lowering agents for Alzheimer's disease?

  2010cites this paper
• Quantitative measurement of specific biomarkers for protein oxidation, nitration and glycation in Arabidopsis leaves.

  2009cites this paper
• Analysis of advanced glycation endproducts in dairy products by isotope dilution liquid chromatography-electrospray tandem mass spectrometry. The particular case of carboxymethyllysine.

  2009cites this paper
• Determination of Nɛ-(carboxymethyl)lysine in food systems by ultra performance liquid chromatography-mass spectrometry

  2009cites this paper
• Nutritional and sanitary impact of nuts and seeds roasting: the interest of using fluorescence spectroscopy as a tool to control neoformed compounds

  2009cites this paper
• Elevation of the glycoxidation product Nε-(carboxymethyl)lysine in patients presenting with acute myocardial infarction

  2009cites this paper
• Dissociation of functional status from accrual of CML and RAGE in the aged mouse brain.

  2008cites this paper
• Determination ofNɛ‐(Carboxymethyl)lysine in Foods and Related Systems

  2008cites this paper
• Advanced glycation end products and cardiovascular disease.

  2008cites this paper
• Reconstructed skin modified by glycation of the dermal equivalent as a model for skin aging and its potential use to evaluate anti-glycation molecules.

  2008cites this paper
• Vitamin C–mediated Maillard Reaction in the Lens Probed in a Transgenic‐mouse Model

  2008cites this paper
• Identification of CML-modified Proteins in Hemofiltrate of Diabetic Patients by Proteome Analysis

  2007cites this paper
• Advanced glycoxidation

  2007cites this paper
• The road to advanced glycation end products: a mechanistic perspective.

  2007cites this paper
• Evaluation of a gas chromatography/mass spectrometry method for the quantification of carboxymethyllysine in food samples.

  2007cites this paper
• Simultaneous analysis of lysine, Nɛ-carboxymethyllysine and lysinoalanine from proteins

  2007cites this paper
• Simultaneous analysis of lysine, Nepsilon-carboxymethyllysine and lysinoalanine from proteins.

  2007cites this paper
• Modifications of milk constituents during processing: A preliminary benchmarking study

  2006cites this paper
• Vitamin C mediates chemical aging of lens crystallins by the Maillard reaction in a humanized mouse model

  2006cites this paper
• Synthesis, tandem MS- and NMR-based characterization, and quantification of the carbon 13-labeled advanced glycation endproduct, 6-N-carboxymethyllysine

  2006cites this paper
• Inhibition of advanced glycation end product formation on collagen by rutin and its metabolites.

  2006cites this paper
• Detection of dideoxyosone intermediates of glycation using a monoclonal antibody: characterization of major epitope structures.

  2006cites this paper
• Mass spectrometry for the study of protein glycation in disease.

  2006cites this paper
• Phage‐Displayed Antibodies for the Detection of Glycated Proteasome in Aging Cells

  2006cites this paper
• Evidence for non‐enzymatic glycosylation of Escherichia coli chromosomal DNA

  2005cites this paper
• Enzyme activity and AGE formation in a model of AST glycoxidation by D-fructose in vitro.

  2005cites this paper
• Pyridoxamine as a multifunctional pharmaceutical: targeting pathogenic glycation and oxidative damage

  2005cites this paper
• Evaluation of the Maillard Reaction in Infant Formulas by Means of Front‐Face Fluorescence

  2005cites this paper
• Increased accumulation of the glycoxidation product Nepsilon-(carboxymethyl)lysine in hearts of diabetic patients: generation and characterisation of a monoclonal anti-CML antibody.

  2004cites this paper
• 4-Hydroxy-2-nonenal: a product and mediator of oxidative stress.

  2003cites this paper
• Modification of Proteins In Vitro by Physiological Levels of Glucose

  2003cites this paper
• Deoxycytidine glyoxal: lesion induction and evidence of repair following vitamin C supplementation in vivo.

  2003cites this paper
• Carbonyl Stress and Diabetic Complications

  2003cites this paper
• Paradoxical Impact of Antioxidants on Post-Amadori Glycoxidation

  2003cites this paper
• Vitamin C metabolomic mapping in experimental diabetes with 6-deoxy-6-fluoro-ascorbic acid and high resolution 19F-nuclear magnetic resonance spectroscopy.

  2003cites this paper
• A Post-Amadori Inhibitor Pyridoxamine Also Inhibits Chemical Modification of Proteins by Scavenging Carbonyl Intermediates of Carbohydrate and Lipid Degradation*

  2002cites this paper
• Analysis of glycated and ascorbylated proteins by gas chromatography-mass spectrometry.

  2002cites this paper
• Fortification of milk with iron-ascorbate promotes lysine glycation and tryptophan oxidation

  2002cites this paper
• CML: a brief history

  2002cites this paper
• How hyperglycemia promotes atherosclerosis: molecular mechanisms

  2002cites this paper
• Marked Increases in Macrophage Colony-Stimulating Factor and Interleukin-18 in Maintenance Hemodialysis Patients: Comparative Study of Advanced Glycation End Products, Carboxymethyllysine and Pentosidine

  2002cites this paper
• Glycation by ascorbic acid causes loss of activity of ribulose-1,5-bisphosphate carboxylase/oxygenase and its increased susceptibility to proteases.

  2002cites this paper
• Pyridoxamine inhibits early renal disease and dyslipidemia in the streptozotocin-diabetic rat.

  2002cites this paper
• Crosslinking by advanced glycation end products increases the stiffness of the collagen network in human articular cartilage: a possible mechanism through which age is a risk factor for osteoarthritis.

  2002cites this paper
• Reactive carbonyl compounds related uremic toxicity ("carbonyl stress").

  2001cites this paper
• Carbonyl stress.

  2001cites this paper
• Oxidative Alterations in Neurodegenerative Diseases

  2001cites this paper
• Evidence for non‐enzymatic glycosylation in Escherichia coli

  2001cites this paper
• Chelating Activity of Advanced Glycation End-product Inhibitors*

  2001cites this paper
• Distribution of ferritin and redox-active transition metals in normal and cataractous human lenses.

  2000cites this paper
• 6-Deoxy-6-fluoro-L-ascorbic acid: crystal structure and oxidative degradation.

  2000cites this paper
• 'Carbonyl stress' and dialysis-related amyloidosis.

  2000cites this paper