Non-enzymatic glycation and glycoxidation protein products in foods and diseases: An interconnected, complex scenario fully open to innovative proteomic studies

Mass Spectrometry Reviews

Volumn 33, Issue 1, 2014, Pages 49-77

  Arena, Simona ^a   Salzano, Anna Maria ^a   Renzone, Giovanni ^a   D'Ambrosio, Chiara ^a   Scaloni, Andrea ^a  

^a CNR   (Italy)

Author keywords

glycation; glycoxidation; mass spectrometry; proteomics

Indexed keywords

ADVANCED GLYCATION END PRODUCTS; BIOPHARMACEUTICAL PRODUCTS; GLYCATION; GLYCOXIDATION; MODIFIED AMINO ACIDS; POST-TRANSLATIONAL MODIFICATIONS; PROTEOMIC APPROACHES; PROTEOMICS;

AMINO ACIDS; MASS SPECTROMETRY; MOLECULAR BIOLOGY; NEURODEGENERATIVE DISEASES; PROTEINS;

GLYCOSYLATION;

ADVANCED GLYCATION END PRODUCT; PROTEIN;

AMINO ACID SEQUENCE; ANIMAL; ARTICLE; CHEMISTRY; GLYCATION; GLYCOSYLATION; GLYCOXIDATION; HUMAN; MASS SPECTROMETRY; METABOLISM; METHODOLOGY; MOLECULAR GENETICS; PROTEIN PROCESSING; PROTEOMICS;

GLYCATION; GLYCOXIDATION; MASS SPECTROMETRY; PROTEOMICS;

AMINO ACID SEQUENCE; ANIMALS; GLYCOSYLATION; GLYCOSYLATION END PRODUCTS, ADVANCED; HUMANS; MASS SPECTROMETRY; MOLECULAR SEQUENCE DATA; PROTEIN PROCESSING, POST-TRANSLATIONAL; PROTEINS; PROTEOMICS;

EID: 84889881830     PISSN: 02777037     EISSN: 10982787     Source Type: Journal    
DOI: 10.1002/mas.21378     Document Type: Article

References (282)

1. Ahmad W, Li L, Deng Y,. 2008. Identification of AGE-precursors and AGE formation in glycation-induced BSA peptides. BMB Rep 4: 516-522.
2. Ahmed N, Thornalley PJ, Dawczynski J, Franke S, Strobel J, Stein G, Haik GM,. 2003. Methylglyoxal-derived hydroimidazolone advanced glycation end-products of human lens proteins. Invest Ophthalmol Vis Sci 44: 5287-5292.
3. Ahmed N, Mirshekar-Syahkal B, Kennish L, Karachalias N, Babaei-Jadidi R, Thornalley PJ,. 2005a. Assay of advanced glycation endproducts in selected beverages and food by liquid chromatography with tandem mass spectrometric detection. Mol Nutr Food Res 49: 691-699.
4. Ahmed N, Dobler D, Dean M, Thornalley PJ,. 2005b. Peptide mapping identifies hotspot site of modification in human serum albumin by methylglyoxal involved in ligand binding and esterase activity. J Biol Chem 280: 5724-5732.
5. Ahmed EK, Rogowska-Wrzesinska A, Roepstorff P, Bulteau AL, Friguet B,. 2010. Protein modification and replicative senescence of WI-38 human embryonic fibroblasts. Aging Cell 9: 252-272.
6. Aldini G, Regazzoni L, Orioli M, Rimoldi I, Facino RM, Carini M,. 2008. A tandem MS precursor-ion scan approach to identify variable covalent modification of albumin Cys34: A new tool for studying vascular carbonylation. J Mass Spectrom 43: 1470-1481.
7. Alt N, Carson JA, Alderson NL, Wang Y, Nagai R, Henle T, Thorpe SR, Baynes JW,. 2004. Chemical modification of muscle protein in diabetes. Arch Biochem Biophys 425: 200-206.
8. Ames JM,. 1992. The Maillard reaction. In:, Hudson BJF, editor. Progress in food proteins-biochemistry. London: Elsevier Applied Science. pp 99-153.
9. Ames JM,. 2003. Nonenzymatic browning. In:, Caballero B, Trugo L, Finglas P, editors. Encyclopedia of food sciences and nutrition. London: Academic Press. pp 665-672.
10. Ames JM,. 2005. Application of semiquantitative proteomics techniques to the Maillard reaction. Ann NY Acad Sci 1043: 225-235.
11. Arena S, Renzone G, Novi G, Paffetti A, Bernardini G, Santucci A, Scaloni A,. 2010. Modern proteomic methodologies for the characterization of lactosylation protein targets in milk. Proteomics 10: 3414-3434.
12. Arena S, Renzone G, Novi G, Scaloni A,. 2011. Redox proteomics of fat globules unveils broad protein lactosylation and compositional changes in milk samples subjected to various technological procedures. J Proteomics 74: 2453-2475.
13. Ïμ-(carboxymethyl)lysine in food systems by ultra performance liquid chromatography-mass spectrometry. Amino Acids 36: 317-326.
14. Bachi A, Dalle-Donne I, Scaloni A,. 2013. Redox proteomics: Chemical principles, methodological approaches, and biological/biomedical promises. Chem Rev 113: 596-698.
15. Bai X, Wang Z, Huang C, Wang Z, Chi L,. 2012. Investigation of non-enzymatic glycosylation of human serum albumin using ion trap-time of flight mass spectrometry. Molecules 17: 8782-8794.
16. Bakala H, Hamelin M, Mary J, Borot-Laloi C, Friguet B,. 2012. Catalase, a target of glycation damage in rat liver mitochondria with aging. Biochim Biophys Acta 1822: 1527-1534.
17. Baker JR, Zyzak DV, Thorpe SR, Baynes JW,. 1994. Chemistry of the fructosamine assay: D-glucosone is the product of oxidation of Amadori compounds. Clin Chem 40: 1950-1955.
18. Bantscheff M, Schirle M, Sweetman G, Rick J, Kuster B,. 2007. Quantitative mass spectrometry in proteomics: A critical review. Anal Bioanal Chem 389: 1017-1031.
19. 18O-labeling and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Clin Chim Acta 411: 1102-1110.
20. Barnaby OS, Cerny RL, Clarke W, Hage DS,. 2011. Comparison of modification sites formed on human serum albumin at various stages of glycation. Clin Chim Acta 412: 277-285.
21. Baynes JW, Thorpe SR,. 2000. Glycoxidation and lipoxidation in atherogenesis. Free Radic Biol Med 28: 1708-1716.
22. Bhonsle HS, Korwar AM, Kote SS, Golegaonkar SB, Chougale AD, Shaik ML, Dhande NL, Giri AP, Shelgikar KM, Boppana R, Kulkarni MJ,. 2012. Low plasma albumin levels are associated with increased plasma protein glycation and HbA1c in diabetes. J Proteome Res 11: 1391-1396.
23. 2+-ATPase. Diabetes 53: 463-473.
24. 6-(2,3-dihydroxy-5,6-dioxohexyl)-L- lysinate by LC-(ESI)MS peptide mapping: Evidence for its key role in AGE formation. Bioconjug Chem 14: 619-628.
25. Biemel KM, Bühler HP, Reihl O, Lederer MO,. 2001. Identification and quantitative evaluation of the lysine-arginine crosslinks GODIC, MODIC, DODIC, and glucosepan in foods. Nahrung 45: 210-214.
26. Biemel KM, Conrad J, Lederer MO,. 2002a. Unexpected carbonyl mobility in aminoketoses: The key to major Maillard crosslinks. Angew Chem Int Ed Engl 4: 801-814.
27. Biemel KM, Friedl DA, Lederer MO,. 2002b. Identification and quantification of major Maillard cross-links in human serum albumin and lens protein. Evidence for glucosepane as the dominant compound. J Biol Chem 277: 24907-24915.
28. Bonsignore A, Leoncini G, Siri A, Ricci D,. 1973. Kinetic behaviour of glyceraldehyde 3-phosphate conversion into methylglyoxal. Ital J Biochem 22: 131-140.
29. Bookchin RM, Gallop PM,. 1968. Structure of hemoglobin A1c: Nature of the N-terminal b-chain blocking group. Biochem Biophys Res Commun 32: 86-93.
30. Borges CR, Oran PE, Buddi S, Jarvis JW, Schaab MR, Rehder DS, Rogers SP, Taylor T, Nelson RW,. 2011. Building multidimensional biomarker views of type 2 diabetes on the basis of protein microheterogeneity. Clin Chem 57: 719-728.
31. Brancia FL, Bereszczak JZ, Lapolla A, Fedele D, Baccarin L, Seraglia R, Traldi P,. 2006. Comprehensive analysis of glycated human serum albumin tryptic peptides by off-line liquid chromatography followed by MALDI analysis on a time-of-flight/curved field reflectron tandem mass spectrometer. J Mass Spectrom 41: 1179-1185.
32. Brock JW, Hinton DJ, Cotham WE, Metz TO, Thorpe SR, Baynes JW, Ames JM,. 2003. Proteomic analysis of the site specificity of glycation and carboxymethylation of ribonuclease. J Proteome Res 2: 506-513.
33. Brock JW, Cotham WE, Thorpe SR, Baynes JW, Ames JM,. 2007. Detection and identification of arginine modifications on methylglyoxal-modified ribonuclease by mass spectrometric analysis. J Mass Spectrom 42: 89-100.
34. Brunner E, Ahrens CH, Mohanty S, Baetschmann H, Loevenich S, Potthast F, Deutsch EW, Panse C, de Lichtenberg U, Rinner O, Lee H, Pedrioli PG, Malmstrom J, Koehler K, Schrimpf S, Krijgsveld J, Kregenow F, Heck AJ, Hafen E, Schlapbach R, Aebersold R,. 2007. A high-quality catalog of the Drosophila melanogaster proteome. Nat Biotechnol 25: 576-583.
35. Calvano CD, Monopoli A, Loizzo P, Faccia M, Zambonin C,. 2013. Proteomic approach based on MALDI-TOF MS to detect powdered milk in fresh cow's milk. J Agric Food Chem 61: 1609-1617.
36. Cantero AV, Portero-Otín M, Ayala V, Auge N, Sanson M, Elbaz M, Thiers JC, Pamplona R, Salvayre R, Nègre-Salvayre A,. 2007. Methylglyoxal induces advanced glycation end product (AGEs) formation and dysfunction of PDGF receptor-beta: Implications for diabetic atherosclerosis. FASEB J 21: 3096-3106.
37. Carulli S, Calvano CD, Palmisano F, Pischetsrieder M,. 2011. MALDI-TOF MS characterization of glycation products of whey proteins in a glucose/galactose model system and lactose-free milk. J Agric Food Chem 59: 1793-1803.
38. Chen L, Wei Y, Wang X, He R,. 2010. Ribosylation rapidly induces alpha-synuclein to form highly cytotoxic molten globules of advanced glycation end products. PLoS ONE 5: e9052.
39. Chougale AD, Bhat SP, Bhujbal SV, Zambare MR, Puntambekar S, Somani RS, Boppana R, Giri AP, Kulkarni MJ,. 2012. Proteomic analysis of glycated proteins from streptozotocin-induced diabetic rat kidney. Mol Biotechnol 50: 28-38.
40. Cocklin RR, Zhang Y, O'Neill KD, Chen NX, Moe SM, Bidasee KR, Wang M,. 2003. Identity and localization of advanced glycation end products on human β2-microglobulin using matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Anal Biochem 314: 322-325.
41. Corzo-Martínez M, Lebrõn-Aguilar R, Villamiel M, Quintanilla-Lõpez JE, Moreno FJ,. 2009. Application of liquid chromatography-tandem mass spectrometry for the characterization of galactosylated and tagatosylated β-lactoglobulin peptides derived from in vitro gastrointestinal digestion. J Chromatogr A 1216: 7205-7212.
42. Cotham WE, Metz TO, Ferguson PL, Brock JW, Hinton DJ, Thorpe SR, Baynes JW, Ames JM,. 2004. Proteomic analysis of arginine adducts on glyoxal-modified ribonuclease. Mol Cell Proteomics 3: 1145-1153.
43. Cox J, Mann M,. 2011. Quantitative, high-resolution proteomics for data-driven systems biology. Annu Rev Biochem 80: 273-299.
44. Cravatt BF, Simon GM, Yates JR III., 2007. The biological impact of mass-spectrometry-based proteomics. Nature 450: 991-1000.
45. Cucu T, De Meulenaer B, Devreese B,. 2012. MALDI-based identification of stable hazelnut protein derived tryptic marker peptides. Food Addit Contam Part A Chem Anal Control Expo Risk Assess 29: 1821-1831.
46. da Costa G, Gomes RA, Guerreiro A, Mateus É, Monteiro E, Barroso E, Coelho AV, Freire AP, Cordeiro C,. 2011. Beyond genetic factors in familial amyloidotic polyneuropathy: Protein glycation and the loss of fibrinogen's chaperone activity. PLoS ONE 6: e24850.
47. Dai Z, Nemet I, Shen W, Monnier VM,. 2007. Isolation, purification and characterization of histidino-threosidine, a novel Maillard reaction protein crosslink from threose, lysine and histidine. Arch Biochem Biophys 463: 78-88.
48. Dai Z, Wang B, Sun G, Fan X, Anderson VE, Monnier VM,. 2008. Identification of glucose-derived cross-linking sites in ribonuclease A. J Proteome Res 7: 2756-2768.
49. Dalfõ E, Portero-Otín M, Ayala V, Martínez A, Pamplona R, Ferrer I,. 2005. Evidence of oxidative stress in the neocortex in incidental Lewy body disease. J Neuropathol Exp Neurol 64: 816-830.
50. Degen J, Hellwig M, Henle T,. 2012. 1,2-dicarbonyl compounds in commonly consumed foods. J Agric Food Chem 60: 7071-7079.
51. Delatour T, Hegele J, Parisod V, Richoz J, Maurer S, Steven M, Buetler T,. 2009. Analysis of advanced glycation endproducts in dairy products by isotope dilution liquid chromatography-electrospray tandem mass spectrometry. The particular case of carboxymethyllysine. J Chromatogr A 1216: 2371-2381.
52. Diguet N, Mallat Y, Ladouce R, Clodic G, Prola A, Tritsch E, Blanc J, Larcher JC, Delcayre C, Samuel JL, Friguet B, Bolbach G, Li Z, Mericskay M,. 2011. Muscle creatine kinase deficiency triggers both actin depolymerization and desmin disorganization by advanced glycation end products in dilated cardiomyopathy. J Biol Chem 286: 35007-35019.
53. Dobler D, Ahmed N, Song L, Eboigbodin KE, Thornalley PJ,. 2006. Increased dicarbonyl metabolism in endothelial cells in hyperglycemia induces anoikis and impairs angiogenesis by RGD and GFOGER motif modification. Diabetes 55: 1961-1969.
54. Dupont FO, Gagnon R, Ardilouze JL, Auray-Blais C,. 2011. Determination of glycated and acetylated hemoglobins in cord blood by time-of-flight mass spectrometry. Anal Chem 83: 5245-5252.
55. Erbersdobler HF, Somoza V,. 2007. Forty years of furosine-Forty years of using Maillard reaction products as indicators of the nutritional quality of foods. Mol Nutr Food Res 51: 423-430.
56. Eyre DR, Weis MA, Wu JJ,. 2010. Maturation of collagen ketoimine cross-links by an alternative mechanism to pyridinoline formation in cartilage. J Biol Chem 285: 16675-16682.
57. Facchiano F, D'Arcangelo D, Russo K, Fogliano V, Mennella C, Ragone R, Zambruno G, Carbone V, Ribatti D, Peschle C, Capogrossi MC, Facchiano A,. 2006. Glycated fibroblast growth factor-2 is quickly produced in vitro upon low-millimolar glucose treatment and detected in vivo in diabetic mice. Mol Endocrinol 20: 2806-2818.
58. Fan X, Zhang J, Theves M, Strauch C, Nemet I, Liu X, Qian J, Giblin FJ, Monnier VM,. 2009. Mechanism of lysine oxidation in human lens crystallins during aging and in diabetes. J Biol Chem 284: 34618-34627.
59. Fan X, Sell DR, Zhang J, Nemet I, Theves M, Lu J, Strauch C, Halushka MK, Monnier VM,. 2010. Anaerobic vs aerobic pathways of carbonyl and oxidant stress in human lens and skin during aging and in diabetes: A comparative analysis. Free Radic Biol Med 49: 847-856.
60. Farah MA, Bose S, Lee JH, Jung HC, Kim Y,. 2005. Analysis of glycated insulin by MALDI-TOF mass spectrometry. Biochim Biophys Acta 1725: 269-282.
61. Fedorova M, Frolov A, Hoffmann R,. 2010. Fragmentation behavior of Amadori-peptides obtained by non-enzymatic glycosylation of lysine residues with ADP-ribose in tandem mass spectrometry. J Mass Spectrom 45: 664-669.
62. Flores-Morales P, Diema C, Vilaseca M, Estelrich J, Luque FJ, Gutiérrez-Oliva S, Toro-Labbé A, Silva E,. 2011. Enhanced reactivity of Lys182 explains the limited efficacy of biogenic amines in preventing the inactivation of glucose-6-phosphate dehydrogenase by methylglyoxal. Bioorg Med Chem 19: 1613-1622.
63. Fogliano V, Monti SM, Visconti A, Randazzo G, Facchiano AM, Colonna G, Ritieni A,. 1998. Identification of a β-lactoglobulin lactosylation site. Biochim Biophys Acta 1388: 295-304.
64. Forrester MT, Thompson JW, Foster MW, Nogueira L, Moseley MA, Stamler JS,. 2009. Proteomic analysis of S-nitrosylation and denitrosylation by resin-assisted capture. Nat Biotechnol 27: 557-559.
65. Frolov A, Hoffmann R,. 2010. Identification and relative quantification of specific glycation sites in human serum albumin. Anal Bioanal Chem 397: 2349-2356.
66. Frolov A, Hoffmann P, Hoffmann R,. 2006. Fragmentation behavior of glycated peptides derived from D-glucose, D-fructose and D-ribose in tandem mass spectrometry. J Mass Spectrom 41: 1459-1469.
67. Frost L, Chaudhry M, Bell T, Cohenford M,. 2011. In vitro galactation of human serum albumin: Analysis of the protein's galactation sites by mass spectrometry. Anal Biochem 410: 248-256.
68. Ïμ-(carboxymethyl) lysine, is a product of both lipid peroxidation and glycoxidation reactions. J Biol Chem 271: 9982-9986.
69. Fu C, Wu C, Liu T, Ago T, Zhai P, Sadoshima J, Li H,. 2009. Elucidation of thioredoxin target protein networks in mouse. Mol Cell Proteomics 8: 1674-1687.
70. Gadgil HS, Bondarenko PV, Treuheit MJ, Ren D,. 2007. Screening and sequencing of glycated proteins by neutral loss scan LC/MS/MS method. Anal Chem 79: 5991-5999.
71. Gao Y, Wang Y,. 2006. Site-selective modifications of arginine residues in human hemoglobin induced by methylglyoxal. Biochemistry 45: 15654-15660.
72. Glomb MA, Pfahler C,. 2001. Amides are novel protein modifications formed by physiological sugars. J Biol Chem 276: 41638-41647.
73. δ-(5- hydroxy-4,6-dimethylpyrimidine-2-yl)-l-ornithine, a novel methylglyoxal-arginine modification in beer. J Agric Food Chem 49: 366-372.
74. Gobert J, Glomb MA,. 2009. Degradation of glucose: Reinvestigation of reactive α-dicarbonyl compounds. J Agric Food Chem 57: 8591-8597.
75. Gomes RA, Vicente Miranda H, Silva MS, Graça G, Coelho AV, Ferreira AE, Cordeiro C, Freire AP, 2006. Yeast protein glycation in vivo by methylglyoxal. Molecular modification of glycolytic enzymes and heat shock proteins. FEBS J 273: 5273-5287.
76. Gomes RA, Oliveira LM, Silva M, Ascenso C, Quintas A, Costa G, Coelho AV, Sousa Silva M, Ferreira AE, Ponces Freire A, Cordeiro C,. 2008. Protein glycation in vivo: Functional and structural effects on yeast enolase. Biochem J 416: 317-326.
77. Gontarev S, Shmanai V, Frey SK, Kvach M, Schweigert FJ,. 2007. Application of phenylboronic acid modified hydrogel affinity chips for high-throughput mass spectrometric analysis of glycated proteins. Rapid Commun Mass Spectrom 21: 1-6.
78. Guedes S, Vitorino R, Domingues MR, Amado F, Domingues P,. 2010. Oxidative modifications in glycated insulin. Anal Bioanal Chem 397: 1985-1995.
79. Guedes S, Vitorino R, Domingues MR, Amado F, Domingues P,. 2011. Glycation and oxidation of histones H2B and H1: In vitro study and characterization by mass spectrometry. Anal Bioanal Chem 399: 3529-3539.
80. Guerrero E, Vasudevaraju P, Hegde ML, Britton GB, Rao KS,. 2013. Recent advances in α-synuclein functions, advanced glycation, and toxicity: Implications for Parkinson's disease. Mol Neurobiol 47: 525-536.
81. Hambsch B, Chen BG, Brenndörfer J, Meyer M, Avrabos C, Maccarrone G, Liu RH, Eder M, Turck CW, Landgraf R,. 2010. Methylglyoxal-mediated anxiolysis involves increased protein modification and elevated expression of glyoxalase 1 in the brain. J Neurochem 113: 1240-1251.
82. Hamelin M, Mary J, Vostry M, Friguet B, Bakala H,. 2007. Glycation damage targets glutamate dehydrogenase in the rat liver mitochondrial matrix during aging. FEBS J 274: 5949-5961.
83. Han Y, Randell E, Vasdev S, Gill V, Curran M, Newhook LA, Grant M, Hagerty D, Schneider C,. 2009. Plasma advanced glycation endproduct, methylglyoxal-derived hydroimidazolone is elevated in young, complication-free patients with Type 1 diabetes. Clin Biochem 42: 562-569.
84. Hasenkopf K, Rönner B, Hiller H, Pischetsrieder M,. 2002. Analysis of glycated and ascorbylated proteins by gas chromatography-mass spectrometry. J Agric Food Chem 50: 5697-5703.
85. Hashim Z, Zarina S,. 2011. Advanced glycation end products in diabetic and non-diabetic human subjects suffering from cataract. Age 33: 377-384.
86. Hegab Z, Gibbons S, Neyses L, Mamas MA,. 2012. Role of advanced glycation end products in cardiovascular disease. World J Cardiol 4: 90-102.
87. Hegele J, Buetler T, Delatour T,. 2008. Comparative LC-MS/MS profiling of free and protein-bound early and advanced glycation-induced lysine modifications in dairy products. Anal Chim Acta 617: 85-96.
88. Held JM, Danielson SR, Behring JB, Atsriku C, Britton DJ, Puckett RL, Schilling B, Campisi J, Benz CC, Gibson BW,. 2010. Targeted quantitation of site-specific cysteine oxidation in endogenous proteins using a differential alkylation and multiple reaction monitoring mass spectrometry approach. Mol Cell Proteomics 9: 1400-1410.
89. Hellwig M, Degen J, Henle T,. 2010. 3-Deoxygalactosone, a "new" 1,2-dicarbonyl compound in milk products. J Agric Food Chem 58: 10752-10760.
90. Henle T,. 2005. Protein-bound advanced glycation endproducts (AGEs) as bioactive amino acid derivatives in foods. Amino Acids 29: 313-322.
91. Henning C, Smuda M, Girndt M, Ulrich C, Glomb MA,. 2011. Molecular basis of Maillard amide-advanced glycation end product (AGE) formation in vivo. J Biol Chem 286: 44350-44356.
92. Hinton DJ, Ames JM,. 2006. Site specificity of glycation and carboxymethylation of bovine serum albumin by fructose. Amino Acids 30: 425-434.
93. Hodge JE,. 1953. Chemistry of browning reactions in model systems. J Agric Food Chem 1: 928-943.
94. Hofmann T,. 1998. Characterization of chemical structure of novel coloured Maillard reaction products from furan-2-carboxaldehyde and amino acids. J Agric Food Chem 46: 932-940.
95. Hollnagel A, Kroh LW,. 2000. Degradation of oligosaccharides in nonenzymatic browning by formation of alpha-dicarbonyl compounds via a "peeling off" mechanism. J Agric Food Chem 48: 6219-6226.
96. Hollnagel A, Kroh LW,. 2002. 3-Deoxypentosulose: An α-dicarbonyl compound predominating in nonenzymatic browning of oligosaccharides in aqueous solution. J Agric Food Chem 50: 1659-1664.
97. Horie K, Miyata T, Maeda K, Miyata S, Sugiyama S, Sakai H, van Ypersole de Strihou C, Monnier VM, Witztum JL, Kurokawa K,. 1997. Immunohistochemical colocalization of glycoxidation products and lipid peroxidation products in diabetic renal glomerular lesions. Implication for glycoxidative stress in the pathogenesis of diabetic nephropathy. J Clin Invest 100: 2995-3004.
98. Humeny A, Kislinger T, Becker CM, Pischetsrieder M,. 2002. Qualitative determination of specific protein glycation products by matrix-assisted laser desorption/ionization mass spectrometry peptide mapping. J Agric Food Chem 50: 2153-2160.
99. Ïμ-carboxymethyl lysine protein adduct is a major immunological epitope in proteins modified with advanced glycation end products of the Maillard reaction. Biochemistry 35: 8075-8083.
100. Jaleel A, Halvatsiotis P, Williamson B, Juhasz P, Martin S, Nair KS,. 2005. Identification of Amadori-modified plasma proteins in type 2 diabetes and the effect of short-term intensive insulin treatment. Diabetes Care 28: 645-652.
101. Johansen MB, Kiemer L, Brunak S,. 2006. Analysis and prediction of mammalian protein glycation. Glycobiology 16: 844-853.
102. Ïμ- carboxymethyl lysine in the human epidermis. Biochim Biophys Acta 1814: 1246-1252.
103. Kettenbach AN, Rush J, Gerber SA,. 2011. Absolute quantification of protein and post-translational modification abundance with stable isotope-labeled synthetic peptides. Nat Protoc 6: 175-186.
104. 6]glucose as a method of advanced glycation sites identification. Anal Biochem 431: 57-65.
105. Kijewska M, Stefanowicz P, Kluczyk A, Szewczuk Z,. 2011. The isotopic exchange of oxygen as a tool for detection of the glycation sites in proteins. Anal Biochem 419: 81-87.
106. Ïμ- (carboxymethyl)lysine, imidazolone A, and the Amadori product in glycated lysozyme by MALDI-TOF mass spectrometry. J Agric Food Chem 51: 51-57.
107. Kisugi R, Kouzuma T, Yamamoto T, Akizuki S, Miyamoto H, Someya Y, Yokoyama J, Abe I, Hirai N, Ohnishi A,. 2007. Structural and glycation site changes of albumin in diabetic patient with very high glycated albumin. Clin Chim Acta 382: 59-64.
108. Kitamura A, Matsui K, Konoki K, Matsumori N, Murata M, Kawakami T, Aimoto S,. 2011. Lysine proximity significantly affects glycation of lysine-containing collagen model peptides. Bioorg Med Chem 19: 2125-2129.
109. Kiyonami R, Schoen A, Prakash A, Peterman S, Zabrouskov V, Picotti P, Aebersold R, Huhmer A, Domon B,. 2011. Increased selectivity, analytical precision, and throughput in targeted proteomics. Mol Cell Proteomics 10: M110.002931.
110. Koenig RJ, Peterson CM, Jones RL, Saudek C, Lehrman M, Cerami A,. 1976. A correlation of glucose regulation and hemoglobin A1c in diabetes mellitus. N Engl J Med 295: 417-420.
111. Korwar AM, Bhonsle HS, Chougale AD, Kote SS, Gawai KR, Ghole VS, Koppikar CB, Kulkarni MJ,. 2012. Analysis of AGE modified proteins and RAGE expression in HER2/neu negative invasive ductal carcinoma. Biochem Biophys Res Commun 419: 490-494.
112. Krause R, Kühn J, Penndorf I, Knoll K, Henle T,. 2004. N-terminal pyrazinones: A new class of peptide-bound advanced glycation end-products. Amino Acids 27: 9-18.
113. Kueper T, Grune T, Prahl S, Lenz H, Welge V, Biernoth T, Vogt Y, Muhr GM, Gaemlich A, Jung T, Boemke G, Elsässer HP, Wittern KP, Wenck H, Stäb F, Blatt T,. 2007. Vimentin is the specific target in skin glycation. Structural prerequisites, functional consequences, and role in skin aging. J Biol Chem 282: 23427-23436.
114. Kumar PA, Kumar MS, Reddy GB,. 2007. Effect of glycation on α-crystallin structure and chaperone-like function. Biochem J 408: 251-258.
115. Kuster B, Schirle M, Mallick P, Aebersold R,. 2005. Scoring proteomes with proteotypic peptide probes. Nat Rev Mol Cell Biol 6: 577-583.
116. Langer AK, Poon HF, Münch G, Lynn BC, Arendt T, Butterfield DA,. 2006. Identification of AGE-modified proteins in SH-SY5Y and OLN-93 cells. Neurotox Res 9: 255-268.
117. Lapolla A, Fedele D, Plebani M, Garbeglio M, Seraglia R, D'Alpaos M, Aricò CN, Traldi P,. 1999. Direct evaluation of glycated and glyco-oxidized globins by matrix-assisted laser desorption/ionization mass spectrometry. Rapid Commun Mass Spectrom 13: 8-14.
118. Lapolla A, Fedele D, Reitano R, Aricò NC, Seraglia R, Traldi P, Marotta E, Tonani R,. 2004. Enzymatic digestion and mass spectrometry in the study of advanced glycation end products/peptides. J Am Soc Mass Spectrom 15: 496-509.
119. Lapolla A, Tubaro M, Fedele D, Reitano R, Aricò NC, Ragazzi E, Seraglia R, Vogliardi S, Traldi P,. 2005. A matrix-assisted laser desorption/ionization mass spectrometry study of the non-enzymatic glycation products of human globins in diabetes. Rapid Commun Mass Spectrom 19: 162-168.
120. Lapolla A, Fedele D, Seraglia R, Traldi P,. 2006. The role of mass spectrometry in the study of non-enzymatic protein glycation in diabetes: An update. Mass Spectrom Rev 25: 775-797.
121. Lapolla A, Ragazzi E, Andretta B, Fedele D, Tubaro M, Seraglia R, Molin L, Traldi P,. 2007. Multivariate analysis of matrix-assisted laser desorption/ionization mass spectrometric data related to glycoxidation products of human globins in nephropathic patients. J Am Soc Mass Spectrom 18: 1018-1023.
122. Lapolla A, Brioschi M, Banfi C, Tremoli E, Bonfante L, Cristoni S, Seraglia R, Traldi P,. 2008. On the search for glycated lipoprotein ApoA-I in the plasma of diabetic and nephropathic patients. J Mass Spectrom 43: 74-81.
123. Larsen MR, Trelle MB, Thingholm TE, Jensen ON,. 2006. Analysis of posttranslational modifications of proteins by tandem mass spectrometry. Biotechniques 40: 790-798.
124. Lastovickova M, Bobalova J,. 2012. MS based proteomic approaches for analysis of barley malt. J Cereal Sci 56: 519-530.
125. Ledl F, Schleicher E,. 1990. New aspects of the Maillard reaction in foods and in the human-body. Angew Chem Int Ed 29: 565-594.
126. Lee JH, Kim Y, Ha MY, Lee EK, Choo J,. 2005. Immobilization of aminophenylboronic acid on magnetic beads for the direct determination of glycoproteins by matrix assisted laser desorption ionization mass spectrometry. J Am Soc Mass Spectrom 16: 1456-1460.
127. Li YM, Tan AX, Vlassara H,. 1995. Antibacterial activity of lysozyme and lactoferrin is inhibited by binding of advanced glycation-modified proteins to a conserved motif. Nat Med 1: 1057-1061.
128. Li Y, Jeppsson JO, Jörntén-Karlsson M, Linné Larsson E, Jungvid H, Galaev IY, Mattiasson B,. 2002. Application of shielding boronate affinity chromatography in the study of the glycation pattern of haemoglobin. J Chromatogr B 776: 149-160.
129. Lima M, Moloney C, Ames JM,. 2009. Ultra performance liquid chromatography-mass spectrometric determination of the site specificity of modification of beta-casein by glucose and methylglyoxal. Amino Acids 36: 475-481.
130. Linetsky M, Kaid Johar SR, Meltretter J, Padmanabha S, Parmar T, Vasavada AR, Pischetsrieder M, Nagaraj RH, 2011. Determination of dideoxyosone precursors of AGEs in human lens proteins. Arch Biochem Biophys 514: 16-26.
131. Losito I, Carbonara T, Monaci L, Palmisano F,. 2007. Evaluation of the thermal history of bovine milk from the lactosylation of whey proteins: An investigation by liquid chromatography-electrospray ionization mass spectrometry. Anal Bioanal Chem 389: 2065-2074.
132. Lund T, Svindland A, Pepaj M, Jensen AB, Berg JP, Kilhovd B, Hanssen KF,. 2011. Fibrin(ogen) may be an important target for methylglyoxal-derived AGE modification in elastic arteries of humans. Diab Vasc Dis Res 8: 284-294.
133. Madian AG, Regnier FE,. 2010. Profiling carbonylated proteins in human plasma. J Proteome Res 9: 1330-1343.
134. Madian AG, Myracle AD, Diaz-Maldonado N, Rochelle NS, Janle EM, Regnier FE,. 2011a. Differential carbonylation of proteins as a function of in vivo oxidative stress. J Proteome Res 10: 3959-3972.
135. Madian AG, Myracle AD, Diaz-Maldonado N, Rochelle NS, Janle EM, Regnier FE,. 2011b. Determining the effects of antioxidants on oxidative stress induced carbonylation of proteins. Anal Chem 83: 9328-9336.
136. Maillard LC,. 1912. Action of amino acids on sugars. Formation of melanoidins in a methodical way. Compt Rend 154: 66-68.
137. Makita Z, Vlassara H, Rayfield E, Cartwright K, Friedman E, Rodby R, Cerami A, Bucala R,. 1992a. Hemoglobin-AGE: A circulating marker of advanced glycosylation. Science 258: 651-653.
138. Makita Z, Vlassara H, Cerami A, Bucala R,. 1992b. Immunochemical detection of advanced glycosylation end products in vivo. J Biol Chem 267: 5133-5138.
139. Mann M, Jensen ON,. 2003. Proteomic analysis of post-translational modifications. Nat Biotechnol 21: 255-261.
140. Marotta E, Lapolla A, Fedele D, Senesi A, Reitano R, Witt M, Seraglia R, Traldi P,. 2003. Accurate mass measurements by Fourier transform mass spectrometry in the study of advanced glycation end products/peptides. J Mass Spectrom 38: 196-205.
141. Martins SI, Marcelis AT, van Boekel MA,. 2003. Kinetic modelling of Amadori N-(1-deoxy-D-fructos-1-yl)-glycine degradation pathways. Part I-Reaction mechanism. Carbohydr Res 338: 1651-1663.
142. Mavric E, Henle T,. 2006. Isolation and identification of 3,4-dideoxypentosulose as specific degradation product of oligosaccharides with 1,4-glycosidic linkages. Eur Food Res Technol 223: 803-810.
143. Meltretter J, Seeber S, Humeny A, Becker CM, Pischetsrieder M,. 2007. Site-specific formation of Maillard, oxidation, and condensation products from whey proteins during reaction with lactose. J Agric Food Chem 55: 6096-6103.
144. Meltretter J, Becker CM, Pischetsrieder M,. 2008. Identification and site-specific relative quantification of beta-lactoglobulin modifications in heated milk and dairy products. J Agric Food Chem 56: 5165-5171.
145. ω-(carboxymethyl)arginine by a specific antibody. Ann NY Acad Sci 1126: 155-157.
146. Ïμ-carboxyethyl lysine (CEL): Possible involvement in the removal of CEL-modified proteins by macrophages. Biochem Biophys Res Commun 407: 420-425.
147. Ïμ-carboxymethyllysine in the milk proteome. Proteomics 11: 420-428.
148. Mikulíková K, Eckhardt A, Pataridis S, Miksík I,. 2007. Study of posttranslational non-enzymatic modifications of collagen using capillary electrophoresis/mass spectrometry and high performance liquid chromatography/mass spectrometry. J Chromatogr A 1155: 125-133.
149. Miller AK, Hambly DM, Kerwin BA, Treuheit MJ, Gadgil HS,. 2011. Characterization of site-specific glycation during process development of a human therapeutic monoclonal antibody. J Pharm Sci 100: 2543-2550.
150. Mitsuhashi T, Li YM, Fishbane S, Vlassara H,. 1997. Depletion of reactive advanced glycation endproducts from diabetic uremic sera using a lysozyme-linked matrix. J Clin Invest 100: 847-854.
151. Mittelmaier S, Pischetsrieder M,. 2011. Multistep ultrahigh performance liquid chromatography/tandem mass spectrometry analysis for untargeted quantification of glycating activity and identification of most relevant glycation products. Anal Chem 83: 9660-9668.
152. Mittelmaier S, Niwa T, Pischetsrieder M,. 2012. Chemical and physiological relevance of glucose degradation products in peritoneal dialysis. J Ren Nutr 22: 181-185.
153. Miyata S, Monnier V,. 1992. Immunohistochemical detection of advanced glycosylation end products in diabetic tissues using monoclonal antibody to pyrraline. J Clin Invest 89: 1102-1112.
154. Miyata T, Inagi R, Wada Y, Ueda Y, Iida Y, Takahashi M, Taniguchi N, Maeda K,. 1994. Glycation of human β 2-microglobulin in patients with hemodialysis-associated amyloidosis: Identification of the glycated sites. Biochemistry 33: 12215-12221.
155. Miyata T, Taneda S, Kawai R, Ueda Y, Horiuchi S, Hara M, Maeda K, Monnier VM,. 1996. Identification of pentosidine as a native structure for advanced glycation end products in β-2-microglobulin-containing amyloid fibrils in patients with dialysis-related amyloidosis. Proc Natl Acad Sci USA 93: 2353-2358.
156. Molin M, Pilon M, Blomberg A,. 2007. Dihydroxyacetone-induced death is accompanied by advanced glycation endproduct formation in selected proteins of Saccharomyces cerevisiae and Caenorhabditis elegans. Proteomics 7: 3764-3774.
157. Mollé D, Morgan F, Bouhallab S, Léonil J,. 1998. Selective detection of lactolated peptides in hydrolysates by liquid chromatography/ electrospray tandem mass spectrometry. Anal Biochem 259: 152-161.
158. Monnier VM, Cerami A,. 1981. Nonenzymatic browning in vivo: Possible process for aging of long-lived proteins. Science 211: 491-493.
159. Montgomery H, Tanaka K, Belgacem O,. 2010. Glycation pattern of peptides condensed with maltose, lactose and glucose determined by ultraviolet matrix-assisted laser desorption/ionization tandem mass spectrometry. Rapid Commun Mass Spectrom 24: 841-848.
160. Morgan F, Léonil J, Mollé D, Bouhallab S,. 1997. Nonenzymatic lactosylation of bovine β-lactoglobulin under mild heat treatment leads to structural heterogeneity of the glycoforms. Biochem Biophys Res Commun 236: 413-417.
161. Ïμ-carboxymethyl lysine (CML) in keratin of skin. J Chromatogr B 879: 3303-3309.
162. Mouls L, Silajdzic E, Haroune N, Spickett CM, Pitt AR,. 2009. Development of novel mass spectrometric methods for identifying HOCl-induced modifications to proteins. Proteomics 9: 1617-1631.
163. Muntané G, Dalfõ E, Martínez A, Rey MJ, Avila J, Pérez M, Portero M, Pamplona R, Ayala V, Ferrer I,. 2006. Glial fibrillary acidic protein is a major target of glycoxidative and lipoxidative damage in Pick's disease. J Neurochem 99: 177-185.
164. Murdaugh LS, Dillon J, Gaillard ER,. 2009. Modifications to the basement membrane protein laminin using glycolaldehyde and A2E: A model for aging in Bruch's membrane. Exp Eye Res 89: 187-192.
165. Nagai R, Fujiwara Y, Mera K, Motomura K, Iwao Y, Tsurushima K, Nagai M, Takeo K, Yoshitomi M, Otagiri M, Ikeda T,. 2008. Usefulness of antibodies for evaluating the biological significance of AGEs. Ann NY Acad Sci 1126: 38-41.
166. Nagaraj RH, Linetsky M, Stitt AW,. 2012. The pathogenic role of Maillard reaction in the aging eye. Amino Acids 42: 1205-1220.
167. Naito Y, Takagi T, Oya-Ito T, Okada H, Suzuki T, Hirata I, Hirai M, Uchiyama K, Handa O, Uchida K, Yoshikawa T,. 2009. Impaired gastric ulcer healing in diabetic mice: Role of methylglyoxal. J Physiol Pharmacol 60 (Suppl. 7): 123-130.
168. Nakamura K, Nakazawa Y, Ienaga K,. 1997. Acid-stable fluorescent advanced glycation end products: Vesperlysines A, B, and C are formed as crosslinked products in the Maillard reaction between lysine or proteins with glucose. Biochem Biophys Res Commun 232: 227-230.
169. Namiki M, Hayashi T,. 1975. Development of novel free radicals during amino-carbonyl reaction of sugars with amino acids. J Agric Food Chem 23: 487-491.
170. Namiki M, Hayashi T, Kawakishi S,. 1973. Free radicals developed in the amino-carbonyl reaction of sugars with amino acids. Agric Biol Chem 37: 2935-2936.
171. Nedic O, Lagundzin D, Masnikosa R,. 2012. Posttranslational modifications of the insulin-like growth factor-binding protein 3 in patients with type 2 diabetes mellitus assessed by affinity chromatography. J Chromatogr B 904: 93-98.
172. Nemet I, Strauch CM, Monnier VM,. 2011. Favored and disfavored pathways of protein crosslinking by glucose: Glucose lysine dimer (GLUCOLD) and crossline versus glucosepane. Amino Acids 40: 167-181.
173. Nguyen S, Pascariu M, Ghitescu L,. 2006. Early glycation products of endothelial plasma membrane proteins in experimental diabetes. Biochim Biophys Acta 1762: 94-102.
174. Ni J, Yuan X, Gu J, Yue X, Gu X, Nagaraj RH, Crabb JW, Clinical Genomic and Proteomic AMD Study Group. 2009. Plasma protein pentosidine and carboxymethyllysine, biomarkers for age-related macular degeneration. Mol Cell Proteomics 8: 1921-1933.
175. Niwa T,. 2006. Mass spectrometry for the study of protein glycation in disease. Mass Spectrom Rev 25: 713-723.
176. Niwa T, Katsuzaki T, Ishizaki Y, Hayase F, Miyazaki T, Uematsu T, Tatemichi N, Takei Y,. 1997. Imidazolone, a novel advanced glycation end product, is present at high levels in kidneys of rats with streptozotocin- induced diabetes. FEBS Lett 407: 297-302.
177. Niwa T, Naito C, Mawjood AH, Imai K,. 2000. Increased glutathionyl hemoglobin in diabetes mellitus and hyperlipidemia demonstrated by liquid chromatography/electrospray ionization-mass spectrometry. Clin Chem 46: 82-88.
178. Nursten HE,. 2005. The Maillard reaction: Chemistry, biochemistry, and implications. Cambridge: Royal Society of Chemistry.
179. Odani H, Shinzato T, Usami J, Matsumoto Y, Brinkmann Frye E, Baynes JW, Maeda K, 1998. Imidazolium crosslinks derived from reaction of lysine with glyoxal and methylglyoxal are increased in serum proteins of uremic patients: Evidence for increased oxidative stress in uremia. FEBS Lett 427: 381-385.
180. ω- carboxymethylarginine, a new advanced glycation endproduct in serum proteins of diabetic patients: Possibility of a new marker of aging and diabetes. Biochem Biophys Res Commun 285: 1232-1236.
181. Oliveira LM, Lages A, Gomes RA, Neves H, Família C, Coelho AV, Quintas A,. 2011. Insulin glycation by methylglyoxal results in native-like aggregation and inhibition of fibril formation. BMC Biochem 12: 41.
182. Ong SE, Mann M,. 2005. Mass spectrometry-based proteomics turns quantitative. Nat Chem Biol 1: 252-262.
183. Oya-Ito T, Naito Y, Takagi T, Handa O, Matsui H, Yamada M, Shima K, Yoshikawa T,. 2011. Heat-shock protein 27 (Hsp27) as a target of methylglyoxal in gastrointestinal cancer. Biochim Biophys Acta 1812: 769-881.
184. Padival AK, Crabb JW, Nagaraj RH,. 2003. Methylglyoxal modifies heat shock protein 27 in glomerular mesangial cells. FEBS Lett 551: 113-118.
185. Pampati PK, Suravajjala S, Dain JA,. 2011. Monitoring nonenzymatic glycation of human immunoglobulin G by methylglyoxal and glyoxal: A spectroscopic study. Anal Biochem 408: 59-63.
186. Pamplona R, Portero-Otin M, Requena J, Gredilla R, Barja G,. 2002a. Oxidative, glycoxidative and lipoxidative damage to rat heart mitochondrial proteins is lower after 4 months of caloric restriction than in age-matched controls. Mech Ageing Dev 123: 1437-1446.
187. Ïμ-(malondialdehyde)lysine in rat heart mitochondrial proteins. Free Radic Res 36: 47-54.
188. Pamplona R, Dalfõ E, Ayala V, Bellmunt MJ, Prat J, Ferrer I, Portero-Otín M,. 2005. Proteins in human brain cortex are modified by oxidation, glycoxidation, and lipoxidation. Effects of Alzheimer disease and identification of lipoxidation targets. J Biol Chem 280: 21522-21530.
189. Pamplona R, Naudi A, Gavin R, Pastrana MA, Sajnani G, Ilieva EV, Del Rio JA, Portero-Otin M, Ferrer I, Requena JR,. 2008. Increased oxidation, glycoxidation, and lipoxidation of brain proteins in prion disease. Free Radic Biol Med 45: 1159-1168.
190. Park YS, Koh YH, Takahashi M, Miyamoto Y, Suzuki K, Dohmae N, Takio K, Honke K, Taniguchi N,. 2003. Identification of the binding site of methylglyoxal on glutathione peroxidase: Methylglyoxal inhibits glutathione peroxidase activity via binding to glutathione binding sites Arg184 and 185. Free Radic Res 37: 205-211.
191. Pashikanti S, Boissonneault GA, Cervantes-Laurean D,. 2011. Ex vivo detection of histone H1 modified with advanced glycation end products. Free Radic Biol Med 50: 1410-1416.
192. Pedchenko VK, Chetyrkin SV, Chuang P, Ham AJ, Saleem MA, Mathieson PW, Hudson BG, Voziyan PA,. 2005. Mechanism of perturbation of integrin-mediated cell-matrix interactions by reactive carbonyl compounds and its implication for pathogenesis of diabetic nephropathy. Diabetes 54: 2952-2960.
193. Pereira Morais M, Mackay JD, Bhamra SK, Buchanan JG, James TD, Fossey JS, van den Elsen JM, 2010. Analysis of protein glycation using phenylboronate acrylamide gel electrophoresis. Proteomics 10: 48-58.
194. Perkins BA, Rabbani N, Weston A, Ficociello LH, Adaikalakoteswari A, Niewczas M, Warram J, Krolewski AS, Thornalley P,. 2012. Serum levels of advanced glycation endproducts and other markers of protein damage in early diabetic nephropathy in type 1 diabetes. PLoS ONE 7: e35655.
195. Peterson KP, Pavlovich JG, Goldstein D, Little R, England J, Peterson CM,. 1998. What is hemoglobin A1c? An analysis of glycated hemoglobins by electrospray ionization mass spectrometry. Clin Chem 44: 1951-1958.
196. Petersson AS, Steen H, Kalume DE, Caidahl K, Roepstorff P,. 2001. Investigation of tyrosine nitration in proteins by mass spectrometry. J Mass Spectrom 36: 616-625.
197. Phanstiel D, Unwin R, McAlister GC, Coon JJ,. 2009. Peptide quantification using 8-plex isobaric tags and electron transfer dissociation tandem mass spectrometry. Anal Chem 81: 1693-1698.
198. Pischetsrieder M, Henle T,. 2012. Glycation products in infant formulas: Chemical, analytical and physiological aspects. Amino Acids 42: 1111-1118.
199. Poggioli S, Bakala H, Friguet B,. 2002. Age-related increase of protein glycation in peripheral blood lymphocytes is restricted to preferential target proteins. Exp Gerontol 37: 1207-1215.
200. Priego-Capote F, Sanchez JC,. 2009. Strategies for Proteomic analysis of non-enzymatically glycated proteins. Mass Spectrom Rev 28: 135-146.
201. 13C-reducing sugars for quantitative analysis of glycated proteins in human plasma. Mol Cell Proteomics 9: 579-592.
202. 6-reducing sugars. Methods Mol Biol 728: 219-232.
203. Priego-Capote F, Ramirez-Boo M, Hoogland C, Scherl A, Mueller M, Lisacek F, Sanchez JC,. 2011b. Human hemolysate glycated proteome. Anal Chem 83: 5673-5680.
204. Quan C, Alcala E, Petkovska I, Matthews D, Canova-Davis E, Taticek R, Ma S,. 2008. A study in glycation of a therapeutic recombinant humanized monoclonal antibody: Where it is, how it got there, and how it affects charge-based behavior. Anal Biochem 373: 179-191.
205. Queisser MA, Yao D, Geisler S, Hammes HP, Lochnit G, Schleicher ED, Brownlee M, Preissner KT,. 2010. Hyperglycemia impairs proteasome function by methylglyoxal. Diabetes 59: 670-678.
206. Rabbani N, Thornalley PJ,. 2012a. Glycation research in amino acids: A place to call home. Amino Acids 42: 1087-1096.
207. Rabbani N, Thornalley PJ,. 2012b. Methylglyoxal, glyoxalase 1 and the dicarbonyl proteome. Amino Acids 42: 1133-1142.
208. Rabbani N, Chittari MV, Bodmer CW, Zehnder D, Ceriello A, Thornalley PJ,. 2010. Increased glycation and oxidative damage to apolipoprotein B100 of LDL cholesterol in patients with type 2 diabetes and effect of metformin. Diabetes 59: 1038-1045.
209. Rabbani N, Godfrey L, Xue M, Shaheen F, Geoffrion M, Milne R, Thornalley PJ,. 2011. Glycation of LDL by methylglyoxal increases arterial atherogenicity: A possible contributor to increased risk of cardiovascular disease in diabetes. Diabetes 60: 1973-1980.
210. Ramírez-Boo M, Priego-Capote F, Hainard A, Gluck F, Burkhard P, Sanchez JC,. 2012. Characterization of the glycated human cerebrospinal fluid proteome. J Proteomics 75: 4766-4782.
211. Roberts NB, Amara AB, Morris M, Green BN,. 2001. Long-term evaluation of electrospray ionization mass spectrometric analysis of glycated hemoglobin. Clin Chem 47: 316-321.
212. Robinson RA, Evans AR,. 2012. Enhanced sample multiplexing for nitrotyrosine-modified proteins using combined precursor isotopic labeling and isobaric tagging. Anal Chem 84: 4677-4686.
213. Rosca MG, Mustata TG, Kinter MT, Ozdemir AM, Kern TS, Szweda LI, Brownlee M, Monnier VM, Weiss MF,. 2005. Glycation of mitochondrial proteins from diabetic rat kidney is associated with excess superoxide formation. Am J Physiol Renal Physiol 289: F420-F430.
214. Ruiz MC, Portero-Otín M, Pamplona R, Requena JR, Prat J, Lafarga MA, Borràs M, Bellmunt MJ,. 2003. Chemical and immunological characterization of oxidative nonenzymatic protein modifications in dialysis fluids. Perit Dial Int 23: 23-32.
215. Sady C, Jiang CL, Chellan P, Madhun Z, Duve Y, Glomb MA, Nagaraj RH,. 2000. Maillard reactions by α-oxoaldehydes: Detection of glyoxal-modified proteins. Biochim Biophys Acta 1481: 255-264.
216. Saraiva MA, Borges CM, Florêncio MH,. 2006a. Reactions of a modified lysine with aldehydic and diketonic dicarbonyl compounds: An electrospray mass spectrometry structure/activity study. J Mass Spectrom 41: 216-228.
217. Saraiva MA, Borges CM, Florêncio MH,. 2006b. Non-enzymatic model glycation reactions-A comprehensive study of the reactivity of a modified arginine with aldehydic and diketonic dicarbonyl compounds by electrospray mass spectrometry. J Mass Spectrom 41: 755-770.
218. Saraiva MA, Borges CM, Florêncio MH,. 2006c. Towards the control and inhibition of glycation-the role of the guanidine reaction center with aldehydic and diketonic dicarbonyls. A mass spectrometry study. J Mass Spectrom 41: 1346-1368.
219. Scaloni A, Perillo V, Franco P, Fedele E, Froio R, Ferrara L, Bergamo P,. 2002. Characterization of heat-induced lactosylation products in caseins by immunoenzymatic and mass spectrometric methodologies. Biochim Biophys Acta 1598: 30-39.
220. Ïμ-carboxymethyllysine and its precursor, lysine, in exhaled breath condensate using isotope-dilution-hydrophilic-interaction liquid chromatography coupled to tandem mass spectrometry. Anal Bioanal Chem 387: 2783-2791.
221. Sell DR, Monnier VM,. 2004. Conversion of arginine into ornithine by advanced glycation in senescent human collagen and lens crystallins. J Biol Chem 279: 54173-54184.
222. Sell DR, Monnier VM,. 2012. Molecular basis of arterial stiffening: Role of glycation-A mini-review. Gerontology 58: 227-237.
223. Sell DR, Biemel KM, Reihl O, Lederer MO, Strauch CM, Monnier VM,. 2005. Glucosepane is a major protein cross-link of the senescent human extracellular matrix. Relationship with diabetes. J Biol Chem 280: 12310-12315.
224. Shao CH, Rozanski GJ, Nagai R, Stockdale FE, Patel KP, Wang M, Singh J, Mayhan WG, Bidasee KR,. 2010. Carbonylation of myosin heavy chains in rat heart during diabetes. Biochem Pharmacol 80: 205-217.
225. Shao CH, Capek HL, Patel KP, Wang M, Tang K, DeSouza C, Nagai R, Mayhan W, Periasamy M, Bidasee KR,. 2011. Carbonylation contributes to SERCA2a activity loss and diastolic dysfunction in a rat model of type 1 diabetes. Diabetes 60: 947-959.
226. Shao CH, Tian C, Ouyang S, Moore CJ, Alomar F, Nemet I, D'Souza A, Nagai R, Kutty S, Rozanski GJ, Ramanadham S, Singh J, Bidasee KR,. 2012. Carbonylation induces heterogeneity in cardiac ryanodine receptor function in diabetes mellitus. Mol Pharmacol 82: 383-399.
227. Shiio Y, Aebersold R,. 2006. Quantitative proteome analysis using isotope-coded affinity tags and mass spectrometry. Nat Protoc 1: 139-145.
228. Shuvaev VV, Laffont I, Serot JM, Fujii J, Taniguchi N, Siest G,. 2001. Increased protein glycation in cerebrospinal fluid of Alzheimer's disease. Neurobiol Aging 22: 397-402.
229. Siciliano R, Rega B, Amoresano A, Pucci P,. 2000. Modern mass spectrometric methodologies in monitoring milk quality. Anal Chem 72: 408-415.
230. Siciliano RA, Mazzeo MF, Arena S, Renzone G, Scaloni A,. 2013. Mass spectrometry for the analysis of protein lactosylation in milk products. Food Res Int (in press).
231. Smales CM, Pepper DS, James DC,. 2001. Evaluation of protein modification during anti-viral heat bioprocessing by electrospray ionization mass spectrometry. Rapid Commun Mass Spectrom 15: 351-356.
232. Smuda M, Glomb MA,. 2011. Novel insights into the Maillard catalyzed degradation of maltose. J Agric Food Chem 59: 13254-13264.
233. Snow LM, Fugere NA, Thompson LV,. 2007. Advanced glycation end-product accumulation and associated protein modification in type II skeletal muscle with aging. J Gerontol A Biol Sci Med Sci 62: 1204-1210.
234. Sommerer N, Centeno D, Rossignol M,. 2007. Peptide mass fingerprinting: Identification of proteins by MALDI-TOF. Methods Mol Biol 355: 219-234.
235. Soskic V, Groebe K, Schrattenholz A,. 2008. Nonenzymatic posttranslational protein modifications in ageing. Exp Gerontol 43: 247-257.
236. Ïμ- carboxymethyl lysine content of AGE-BSA systems prepared with and without selected antiglycation agents. J Agric Food Chem 58: 11955-11961.
237. Srikanth R, Wilson J, Bridgewater JD, Numbers JR, Lim J, Olbris MR, Kettani A, Vachet RW,. 2007. Improved sequencing of oxidized cysteine and methionine containing peptides using electron transfer dissociation. J Am Soc Mass Spectrom 18: 1499-1506.
238. Sroga GE, Karim L, Colõn W, Vashishth D,. 2011. Biochemical characterization of major bone-matrix proteins using nanoscale-size bone samples and proteomics methodology. Mol Cell Proteomics 10: M110.006718.
239. Steen H, Mann M,. 2002. Analysis of bromotryptophan and hydroxyproline modifications by high-resolution, high-accuracy precursor ion scanning utilizing fragment ions with mass-deficient mass tags. Anal Chem 74: 6230-6236.
240. Stefanowicz P, Kijewska M, Kluczyk A, Szewczuk Z,. 2010. Detection of glycation sites in proteins by high-resolution mass spectrometry combined with isotopic labeling. Anal Biochem 400: 237-243.
241. Takahashi M, Lu YB, Myint T, Fujii J, Wada Y, Taniguchi N,. 1995. In vivo glycation of aldehyde reductase, a major 3-deoxyglucosone reducing enzyme: Identification of glycation sites. Biochemistry 34: 1433-1438.
242. Takátsy A, Böddi K, Nagy L, Nagy G, Szabõ S, Markõ L, Wittmann I, Ohmacht R, Ringer T, Bonn GK, Gjerde D, Szabõ Z,. 2009. Enrichment of Amadori products derived from the nonenzymatic glycation of proteins using microscale boronate affinity chromatography. Anal Biochem 393: 8-22.
243. Takeuchi M, Yanase Y, Matsuura N, Yamagishi Si S, Kameda Y, Bucala R, Makita Z, 2001. Immunological detection of a novel advanced glycation end-product. Mol Med 7: 783-791.
244. Ïμ- (carboxyethyl)lysine in human plasma protein by stable-isotope-dilution tandem mass spectrometry. Clin Chem 50: 1222-1228.
245. Ter Haar R, Westphal Y, Wierenga PA, Schols HA, Gruppen H, 2011. Cross-linking behavior and foaming properties of bovine α-lactalbumin after glycation with various saccharides. J Agric Food Chem 59: 12460-12466.
246. Tessier FJ,. 2010. The Maillard reaction in the human body. The main discoveries and factors that affect glycation. Pathol Biol 58: 214-219.
247. Tessier FJ, Monnier VM, Sayre LM, Kornfield JA,. 2003. Triosidines: Novel Maillard reaction products and cross-links from the reaction of triose sugars with lysine and arginine residues. Biochem J 369: 705-719.
248. Thornalley PJ, Langborg A, Minhas HS,. 1999. Formation of glyoxal, methylglyoxal and 3-deoxyglucosone in the glycation of proteins by glucose. Biochem J 344: 109-116.
249. Thornalley PJ, Battah S, Ahmed N, Karachalias N, Agalou S, Babeai-Jadidi R, Danway A,. 2003. Quantitative screening of advanced glycation endproducts in cellular and extracellular proteins by tandem mass spectrometry. Biochem J 375: 581-592.
250. Unwin RD, Griffiths JR, Whetton AD,. 2009. A sensitive mass spectrometric method for hypothesis-driven detection of peptide post-translational modifications: Multiple reaction monitoring-initiated detection and sequencing (MIDAS). Nat Protoc 4: 870-877.
251. Van Lancker F, Adams A, De Kimpe N,. 2011. Chemical modifications of peptides and their impact on food properties. Chem Rev 111: 7876-7903.
252. Van Schaftingen E, Delpierre G, Collard F, Fortpied J, Gemayel R, Wiame E, Veiga-da-Cunha M,. 2007. Fructosamine 3-kinase and other enzymes involved in protein deglycation. Adv Enzyme Regul 47: 261-269.
253. Viteri G, Carrard G, Birlouez-Aragõn I, Silva E, Friguet B,. 2004. Age-dependent protein modifications and declining proteasome activity in the human lens. Arch Biochem Biophys 427: 197-203.
254. Wa C, Cerny RL, Clarke WA, Hage DS,. 2007. Characterization of glycation adducts on human serum albumin by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Clin Chim Acta 385: 48-60.
255. Washburn MP, Wolters D, Yates JR III., 2001. Large-scale analysis of the yeast proteome by multidimensional protein identification technology. Nat Biotechnol 19: 242-247.
256. Wellner A, Huettl C, Henle T,. 2011. Formation of Maillard reaction products during heat treatment of carrots. J Agric Food Chem 59: 7992-7998.
257. Wells-Knecht KJ, Zyzak DV, Litchfield JE, Thorpe SR, Baynes JW,. 1995. Mechanism of autoxidative glycosylation: Identification of glyoxal and arabinose as intermediates in the autoxidative modification of proteins by glucose. Biochemistry 34: 3702-3709.
258. Wiesner J, Premsler T, Sickmann A,. 2008. Application of electron transfer dissociation (ETD) for the analysis of posttranslational modifications. Proteomics 8: 4466-4483.
259. Willett TL, Kandel R, De Croos JN, Avery NC, Grynpas MD,. 2012. Enhanced levels of non-enzymatic glycation and pentosidine crosslinking in spontaneous osteoarthritis progression. Osteoarthritis Cartilage 20: 736-744.
260. Wu SL, Hühmer AF, Hao Z, Karger BL,. 2007. On-line LC-MS approach combining collision-induced dissociation (CID), electron-transfer dissociation (ETD), and CID of an isolated charge-reduced species for the trace-level characterization of proteins with post-translational modifications. J Proteome Res 6: 4230-4244.
261. Yeboah FK, Alli I, Yaylayan VA, Konishi Y, Stefanowicz P,. 2000. Monitoring glycation of lysozyme by electrospray ionization mass spectrometry. J Agric Food Chem 48: 2766-2774.
262. Yeboah FK, Alli I, Yaylayan VA, Yasuo K, Chowdhury SF, Purisima EO,. 2004. Effect of limited solid-state glycation on the conformation of lysozyme by ESI-MSMS peptide mapping and molecular modeling. Bioconjug Chem 15: 27-34.
263. Ytterberg AJ, Jensen ON,. 2010. Modification-specific proteomics in plant biology. J Proteomics 73: 2249-2266.
264. Zeng J, Davies MJ,. 2005. Evidence for the formation of adducts and S-(carboxymethyl)cysteine on reaction of α-dicarbonyl compounds with thiol groups on amino acids, peptides, and proteins. Chem Res Toxicol 18: 1232-1241.
265. Zeng J, Davies MJ,. 2006. Protein and low molecular mass thiols as targets and inhibitors of glycation reactions. Chem Res Toxicol 19: 1668-1676.
266. Zhang Z,. 2011. Prediction of collision-induced-dissociation spectra of peptides with post-translational or process-induced modifications. Anal Chem 83: 8642-8651.
267. Zhang X, Medzihradszky KF, Cunningham J, Lee PD, Rognerud CL, Ou CN, Harmatz P, Witkowska HE,. 2001. Characterization of glycated hemoglobin in diabetic patients: Usefulness of electrospray mass spectrometry in monitoring the extent and distribution of glycation. J Chromatogr B 759: 1-15.
268. Zhang Y, Cocklin RR, Bidasee KR, Wang M,. 2003. Rapid determination of advanced glycation end products of proteins using MALDI-TOF-MS and PERL script peptide searching algorithm. J Biomol Tech 14: 224-230.
269. Zhang Q, Tang N, Brock JW, Mottaz HM, Ames JM, Baynes JW, Smith RD, Metz TO,. 2007a. Enrichment and analysis of nonenzymatically glycated peptides: Boronate affinity chromatography coupled with electron-transfer dissociation mass spectrometry. J Proteome Res 6: 2323-2330.
270. Zhang Q, Frolov A, Tang N, Hoffmann R, van de Goor T, Metz TO, Smith RD,. 2007b. Application of electron transfer dissociation mass spectrometry in analyses of non-enzymatically glycated peptides. Rapid Commun Mass Spectrom 21: 661-666.
271. Zhang B, Yang Y, Yuk I, Pai R, McKay P, Eigenbrot C, Dennis M, Katta V, Francissen KC,. 2008a. Unveiling a glycation hot spot in a recombinant humanized monoclonal antibody. Anal Chem 80: 2379-2390.
272. 3 versus multi-stage activation tandem mass spectrometry. Rapid Commun Mass Spectrom 22: 3027-3034.
273. Zhang Q, Tang N, Schepmoes AA, Phillips LS, Smith RD, Metz TO,. 2008c. Proteomic profiling of nonenzymatically glycated proteins in human plasma and erythrocyte membranes. J Proteome Res 7: 2025-2032.
274. Zhang Q, Schepmoes AA, Brock JW, Wu S, Moore RJ, Purvine SO, Baynes JW, Smith RD, Metz TO,. 2008d. Improved methods for the enrichment and analysis of glycated peptides. Anal Chem 80: 9822-9829.
275. Zhang Q, Ames JM, Smith RD, Baynes JW, Metz TO,. 2009. A perspective on the Maillard reaction and the analysis of protein glycation by mass spectrometry: Probing the pathogenesis of chronic disease. J Proteome Res 8: 754-769.
276. Zhang G, Huang G, Xiao L, Mitchell AE,. 2011. Determination of advanced glycation endproducts by LC-MS/MS in raw and roasted almonds (Prunus dulcis). J Agric Food Chem 59: 12037-12046.
277. Zhang Q, Monroe ME, Schepmoes AA, Clauss TR, Gritsenko MA, Meng D, Petyuk VA, Smith RD, Metz TO,. 2011c. Comprehensive identification of glycated peptides and their glycation motifs in plasma and erythrocytes of control and diabetic subjects. J Proteome Res 10: 3076-3088.
278. 6-reducing sugars. Anal Chem 84: 2313-2320.
279. Zheng X, Wu SL, Hancock WS,. 2006. Glycation of interferon-β-1b and human serum albumin in a lyophilized glucose formulation. Part III: Application of proteomic analysis to the manufacture of biological drugs. Int J Pharm 322: 136-145.
280. Zhou X, Han P, Li J, Zhang X, Huang B, Ruan HQ, Chen C,. 2010. ESNOQ, proteomic quantification of endogenous S-nitrosation. PLoS ONE 5: e10015.
281. Zmatliková Z, Sedláková P, Lacinová K, Eckhardt A, Pataridis S, Mikšík I,. 2010. Non-enzymatic posttranslational modifications of bovine serum albumin by oxo-compounds investigated by high-performance liquid chromatography-mass spectrometry and capillary zone electrophoresis-mass spectrometry. J Chromatogr A 1217: 8009-8015.
282. Zubarev R, Mann M,. 2007. On the proper use of mass accuracy in proteomics. Mol Cell Proteomics 6: 377-381.