Monitoring glycation of lysozyme by electrospray ionization mass spectrometry

Journal of Agricultural and Food Chemistry

Volumn 48, Issue 7, 2000, Pages 2766-2774

  Yeboah, Faustinus K ^a   Alli, Inteaz ^a   Yaylayan, Varoujan A ^a   Konishi, Yasuo ^b   Stefanowicz, Piotr ^b  

^a MCGILL UNIVERSITY   (Canada)

^b NATIONAL RESEARCH COUNCIL CANADA   (Canada)

Author keywords

D glucosone; D fructose; D glucose; Dehydration; Electrospray mass spectrometry; Glycation; Lysozyme; Oxidation; Reactivity

Indexed keywords

FLUORESCAMINE; FRUCTOSE; GLUCOSE; LYSOZYME; OXYGEN;

ARTICLE; CONTROLLED STUDY; ENZYME ANALYSIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLISM; MODEL; OXIDATION; PROTEIN GLYCOSYLATION;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FLUORESCAMINE; FRUCTOSE; GLUCOSE; MASS SPECTROMETRY; MODELS, CHEMICAL; MURAMIDASE; OXYGEN;

EID: 0033942284     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf990978j     Document Type: Article

References (45)

1. Aeschbacher, H. U. Anticarcinogenic effect of browning reaction products. In The Maillard Reaction in Food Processing, Human Nutrition and Physiology; Finot, P. A., Aeschbacher, H. U., Hurrel, R. F., Liardon, R., Eds.; Birkhauser Verlag: Basel, Switzerland, 1990; pp 335-348.
2. Al-Abed, Y.; Mitsuhashi, T.; Li, H.; Lawson, J. A.; FitzGerald, G. A.; Fonds, H.; Donnelley, T.; Cerami, A.; Ulrich, P.; Bucala, R. Inhibition of advanced glycatiopn end product formation by acetadehyde: Role in the cardioprotective effect of ethanol. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 2385-2390.
3. Baxter, H. J. Free amino acid stability in reducing sugar systems. J. Food Sci. 1995, 60 (2), 405-408.
4. Blakytny, R.; Carver, J. A.; Harding, J. J.; Kilby, G. W.; Sheeil, M. M. A spectroscopic study of glycated bovine a-crystallin: investigation of flexibility of the C-terminal extension, chaperone activity and evidence for diglycation. Biochim. Biophys. Acta 1997, 1343, 299-315.
5. Chuyen, N. V.; Ijichi, K.; Umetus, H.; Moteki, K. Antioxidative properties of products from amino acids or peptides in the reaction with glucose. Adv. Exp. Med. Biol. 1998, 434, 201-212.
6. Davies, C. G. A.; Netto, F. M.; Glassenap, N.; Gallaher, C. M.; Labuza, T. P.; Gallaher, D. D. Indication of the Maillard reaction during storage of protein isolates. J. Agric. Food Chem. 1998, 46, 2485-2489.
7. Finot, P. A.; Magnenat, E. Metabolic transit of early and advanced Maillard products. Prog. Food Nutr. Sci. 1981, 5 (1-6), 193-207.
8. Greenespan, L. Humidity fixed points of binary saturated aqueous solutions. J. Res. Natl. Bur. Stand. 1977, 81A, 89-96.
9. Handa, A.; Kuroda, N. Functional improvement in dried egg white through the Maillard reaction. J. Agric Food Chem. 1999, 47, 1845-1850.
10. Hayase, F.; Hirashima, S.; Okamoto, G.; Kato, H. Scavenging of active oxygens by mellanoidin. In The Maillard Reaction in Food Processing, Human Nutrtition and Physiology; Finot, P. A., Aeschbacher, H. U., Hurrel, R. F., Liardon, R., Eds.; Birkhauser Verlag: Basel, Switzerland, 1990; pp 361-366.
11. Hoffman, T.; Bors, W.; Stettmaier, K. Studies on radical intermediates in the early stage of the nonenzymatic browning reaction of carbohydrates and amino acids. J. Agric. Food Chem. 1999, 47, 379-390.
12. Hurrel, R. F. Influence of the Maillard reaction on the nutritional value of foods. In The Maillard Reaction in Food Processing, Human Nutrtition and Physiology; Finot, P. A., Aeschbacher, H. U., Hurrel, R. F., Liardon, R., Eds.; Birkhauser Verlag: Basel, Switzerland, 1990; pp 245-258.
13. Kato, A.; Sasaki, Y.; Furuta, R.; Kobayashi, K. Functional protein-polysaccharide conjugate prepared by controlled dry-heating of ovalbumin dextran mixtures. J. Agric. Biol. Chem. 1990, 54, 107-112.
14. Kato, A.; Shimokawa, K.; Kobayashi, K. Improvement of the functional properties of insoluble gluten by Pronase digestion followed by dextran conjugation. J. Agric. Food Chem. 1991, 39, 1053-1056.
15. Kato, A.; Nakamura, S.; Takasaki, H.; Maki, S. Novel functional properties of glycosylated lysozyme constructed by chemical and genetic modifications. In Macromolecular Interactions in Food Technology; ACS Symposium Series 650; American Chemical Society: Washington, DC, 1996; pp 243-256.
16. Koschinsky, T.; He, C.-J.; Mitsuhashi, T.; Bucala, R.; Liu, C.; Buenting, C.; Heitmann, K.; Vlassara, H. Orally absorbed reactive glycation products (glycotoxins): An environmental risk factor in diabetic nephropathy. Proc. Natl. Acad. Sci. USA. 1997, 94, 6474-6479.
17. Kubow, S.; Yaylayan, V. A.; Mandeville, S. Protection by acetylsalicyclic acid against hyperglycemia-induced glycation and neural tube defects in cultured early somite mouse embryo. Diabetes Res. 1993, 22, 145-158.
18. Labuza, T. P.; Saltmarch, M. Kinetics of browning and protein quality loss in whey powders during steady state and non-steady-state storage conditions. J. Food Sci. 1981, 47, 92-96, 113.
19. Leonil, J.; Molle, D.; Fauquant, J.; Maubois, J.-L.; Pearce, R. J.; Bouhallab, S. Characterization by ionization mass spectrometry of lactosyl-β-lactoglobulin conjugates formed during heat treatment of milk and whey and identification of one lactose binding site. J. Dairy Sci. 1997, 80, 2270-2281.
20. Lowry, O. H.; Rosebrough, N. J.; Farr, A. L.; Randall, R. J. Protein measurement with the Folin phenol reagent. J. Biol. Chem. 1951, 193, 265-275.
21. Mat Easa, A.; Hill, S. E.; Mitchell, J. R.; Taylor, A. J. Bovin serum albumin gelation as a result of the Maillard reaction. Food Hydrocolloids 1996, 10, 199-202.
22. Molle, D.; Morgan, F.; Bouhallab, S.; Leonil, J. Selective detection of lactolated peptides in hydrolysates by liquid chromatography/electrospray tandem mass spectrometry. Anal. Biochem. 1998, 259, 152-161.
23. Morales, J. F.; Romero, C.; Jimenez-Perez, S. Fluorescence associated with Maillard reaction in milk-resembling systems. Food Chem. 1996, 57 (3), 423-428.
24. Morals, F. J.; van-Boekel, M. A. J. S. A study of advanced Maillard reaction in heated casein/sugar solutions: Fluoresence accumulation. Int. Dairy J. 1997, 695-683.
25. Moreaux, V.; Birlouez-Aragon, I. Degradation of tryptophane in heated β-lactoglobulin-lactose mixtures is associated with intense Maillard reaction. J. Agric. Food Chem. 1997, 45, 1905-1910.
26. Morgan, F.; Leonil, J.; Molle, D.; Bouhallab, S. Non enzymatic lactosylation of bovine β-lactoglobulin under mild heat treatment leads to structural heteroigeneity of the glycoforms. Biochem. Biophys. Res. Commun. 1997, 236, 413-417.
27. Morgan, F.; Bouhallab, S.; Molle, D.; Henry, G.; Maubois, J. L.; Leonil, J. Lactolation of β-lactoglobulin monitored by electrospray ionization mass spectrometry. Int. Dairy J. 1998, 8, 95-98.
28. Morgan, F.; Leonil, J.; Molle, D.; Bouhallab, S. Modification of bovine β-lactoglobulin by glycation in a powdered state or in an aqueous solution: Effect on association behavior and protein conformation. J. Agric. Food Chem. 1999, 47, 83-91.
29. Nakamura, S.; Kato, A.; Kobayashi, K. New antimicrobial characteristics of lysozyme-dextranconjugate. J. Agric. Food Chem. 1991, 39, 645-650.
30. Nakamura, S.; Kato, A.; Kobayashi, K. Enhanced antioxidative effect of ovalbumin due to covalent binding of polysaccharides. J. Agric Food Chem. 1992a, 40, 2033-2037.
31. Nakamura, S.; Kato, A.; Kobayashi, K. Bifunctional lysozyme-galactomannan conjugate having excellent emulsifying properties and antibacterial effects. J. Agric. Food Chem. 1992b, 40, 735-739.
32. Naranjo, G. B.; Malec, L. S.; Vigo, M. S. Reducing sugar effect on available lysine loss of casein by moderate heat treatment. Food Chem. 1998, 62, 309-313.
33. Ortwerth, B. J.; James, H.; Simpson, G.; Linetsky, M. The generation of superoxide anions in glycation reactions with sugars, osones and 3-deoxyosones. Biochem. Biophys Res. Commun. 1998, 245, 161-165.
34. Prabhakaram, M.; Smith, J. B.; Ortwerth, B. J. Rapid assessment of early glycation products by mass spectrometry. Biochem. Mol. Biol. Int. 1996, 40, 315-325.
35. Saeki, H. Preparation of neoglycoprotein from carp myofibrillar protein by Maillard reaction with glucose: Biochemical properties and emulsifying properties. J. Agric. Food Chem. 1997, 45, 680-684.
36. Shu, Y.-W. Effects of the length of polysaccharide chains on the functional properties of the Maillard-type lysozyme-polysaccharide conjugate. J. Agric. Food Chem. 1996, 44, 2544-2548.
37. Suarez, G.; Etlinger, D. J.; Maturana, J.; Weitman, D. Fructated protein is more resistant to ATP-dependent proteolysis than glucated protein possibly as a result of higher content of Maillard fluorophores. Arch. Biochem. Biophys. 1995, 321, 209-213.
38. Tagami, U.; Akashi, S.; Mizukoshi, T.; Susuki, E.; Hirayama, K. Structural studies of the Maillard reaction products of a protein using ion trap mass spectrometry. J. Mass Spectrom. 2000, 35, 131-138.
39. Umetsu, H.; Van Chuyen, N. Digestibility and peptide patterns of modified lysozyme after hydrolyzing by protease. J. Nutr. Sci. Vitaminol. 1998, 44, 291-300.
40. Wells-Knecht, K. J.; Zyzak, D. D.; Litchfield, J. E.; Thorpe, S. R.; Batnes, J. W. mechanism of autoxidative glycosylation: identification of glyoxal and arabinose as intermediates in the autoxidative modification of protein by glucose. Biochemistry 1995, 34, 3702-3709.
41. Wu, H.; Govidarajan, S.; Smith, T.; Rosen, J. D.; Ho, C.-T. Glucose-lysozyme reactions in a restricted water environment. In The Maillard Reaction in Food processing, Human Nutrition and Physiology; Finot, P. A., Aeschbacher, H. U., Hurrel, R. F., Liardon, R., Eds.; Birkhauser Verlag: Basel, Switzerland, 1990; pp 85-90.
42. Yaylayan, A. V.; Huyghues-Despointes, A. Chemistry of Amadori rearrangement products: analysis, synthesis, kinetics, reactions and spectroscopic properties. Crit. Rev. Food Sci. Nutr. 1994, 34 (4), 321-369.
43. Yaylayan, A. V.; Huyghues-Despointes, A.; Polydorides, A. A fluorescamine-based assay for the degree of glycation in bovine serum albumin. Food Res. Int. 1992, 25, 269-275.
44. Yeboah, F. K.; Alli, I.; Yaylayan, V. A. Reactivities of D-glucose and D-fructose during glycation of bovine serum albumin. J. Agric. Food Chem. 1999, 47, 3164-3172.
45. Zigrovic, I.; Versluis, C.; Horvat, S.; Wigger, H. Mass spectrometric characterization of Amadori compounds related to the opioid peptide morphiceptin. Rapid Commun. Mass Spectrom. 1998, 12, 181-187.