Functional changes in β-lactoglobulin by conjugation with cationic saccharides

Journal of Agricultural and Food Chemistry

Volumn 48, Issue 6, 2000, Pages 2050-2056

  Hattori, Makoto ^a   Numamoto, Ken Ichi ^a   Kobayashi, Kazuo ^a   Takahashi, Koji ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

Lactoglobulin; Cationic saccharide; Emulsification; Functional improvement; Lipocalin; Neoglycoconjugate; Protein conjugation; Retinol binding

Indexed keywords

BETA LACTOGLOBULIN; CARBOHYDRATE DERIVATIVE; CHITIN; CHITOPENTAOSE; CHITOSAN; CYANAMIDE; DRUG DERIVATIVE; EMULSIFYING AGENT; GLUCOSAMINE; GLYCOCONJUGATE; LACTOGLOBULIN; OLIGOSACCHARIDE; POLIGLUSAM; UNCLASSIFIED DRUG;

ANIMAL; ANTIGENICITY; ARTICLE; CATTLE; CHEMISTRY; CONFORMATIONAL TRANSITION; CONJUGATION; EMULSION; GLYCATION; IMMUNOGENICITY; KINETICS; METABOLISM; MOLECULAR WEIGHT; NONHUMAN; PROTEIN SECONDARY STRUCTURE; STRUCTURE ANALYSIS;

ANIMALS; CATTLE; CHITIN; CHITOSAN; GLUCOSAMINE; GLYCOCONJUGATES; KINETICS; LACTOGLOBULINS; MAILLARD REACTION; OLIGOSACCHARIDES; PROTEIN STRUCTURE, SECONDARY;

EID: 0033919021     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf991105s     Document Type: Article

References (38)

1. Åkerstrom, B.; Lögdberg, L. An Intriguing Member of the Lipocalin Protein Family: α1-microglobulin. Trends Biochem. Sci. 1990, 15, 240-243.
2. Akita, E. M.; Nakai, S. Lipophilization of β-Lactoglobulin: Effect on Hydrophobicity, Conformation and Surface Functional Properties. J. Food Sci. 1990a, 55, 711-717.
3. Akita, E. M.; Nakai, S. Lipophilization of β-Lactoglobulin: Effect on Allergenicity and Digestibility. J. Food Sci. 1990b, 55, 718-723.
4. Armstrong, J. M.; McKenzie, H. A.; Sawyer, W. H. On the Fractionation of β-Lactoglobulin and α-Lactalbumin. Biochim. Biophys. Acta 1967, 147, 60-72.
5. Bertrand-Harb, C.; Charrier, B.; Dalgalarrondo, M.; Cobert, J. M.; Haertlé, T. Condensation of Glycosidic and Aromatic Structures on Amino Groups of β-Lactoglobulin B via Reductive Alkylation: Solubility and Emulsifying Properties of the Protein Derivatives. Lait 1990, 71, 205-215.
6. Brownlow, S.; Morais, C. J.; Cooper, R.; Flower, D. R.; Yewdall, S. J.; Polikarpov, I.; North, A. C.; Sawyer, L. Bovine β-Lactoglobulin at 1.8 Å Resolution-Still an Enigmatic Lipocalin. Structure 1997, 5, 481-495.
7. Cogan, U.; Kopelman, M.; Mokady, S.; Shintzky, M. Binding Affinities of Retinol and Related Compounds to Retinol Binding Proteins. Eur. J. Biochem. 1976, 65, 71-78.
8. Creuzenet, C.; Touati, A.; Dufour, E.; Choiset, Y.; Chobert, J. M.; Heartlé, T. Acylation and Alkylation of Bovine β-Lactoglobulin in Organic Solvents. J. Agric. Food Chem. 1992, 40, 184-190.
9. Davis, B. J. Disc Electrophoresis - II: Method and Application to Human Serum Proteins. Ann. N. Y. Acad. Sci. 1964, 121, 404-427.
10. Dische, Z.; Borenfreund, E. A Spectrophotometric Method for the Microdetermination of Hexosamines. J. Biol. Chem. 1950, 184, 517-522.
11. Dufour, E.; Dalgalarrondo, M.; Adam, L. Conformation of β-Lactoglobulin at an Oil/water Interface as Determined from Proteolysis and Spectroscopic Methods. J. Colloid Interface Sci. 1998, 207, 264-272.
12. Foegeding, E. A.; Kuhn, P. R.; Hardin, C. C. Specific Divalent Cation-induced Changes during Gelation of β-Lactoglobulin. J. Agric. Food Chem. 1992, 40, 2092-2097.
13. Futterman, S.; Heller, J. The Enhancement of Fluorescence and Decreased Susceptibility to Enzyme Oxidation of Retinol Complexed with Bovine Serum Albumin, β-Lactoglobulin, and the Retinol-Binding Protein of Human Plasma. J. Biol. Chem. 1972, 247, 5168-5172.
14. Hattori, M.; Ametani, A.; Katakura, Y.; Shimizu, M.; Kaminogawa, S. Unfolding/Refolding Studies on Bovine β-Lactoglobulin with Monoclonal Antibodies as Probes: Does a Renatured Protein Completely Refold? J. Biol. Chem. 1993, 268, 22414-22419.
15. Hattori, M.; Nagasawa, K.; Ametani, A.; Kaminogawa, S.; Takahashi, K. Functional Changes in β-Lactoglobulin by Conjugation with Carboxymethyl Dextran. J. Agric. Food Chem. 1994, 42, 2120-2125.
16. Hattori, M.; Aiba, Y.; Nagasawa, K.; Takahashi, K. Functional Improvements of Alginic Acid by Conjugating with β-Lactoglobulin. J. Food Sci. 1996, 61, 1171-1176.
17. Hattori, M.; Ogino, A.; Nakai, H.; Takahashi, K. Functional Improvement of β-Lactoglobulin by Conjugating with Alginate Lyase-Lysate. J. Agric. Food Chem. 1997, 45, 703-708.
18. Hattori, M.; Nagasawa, K.; Ohgata, K.; Sone, N.; Fukuda, A.; Matsuda, H.; Takahashi, K. Reduced Immunogenicity of β-Lactoglobulin by Conjugation with Carboxymethyl Dextran. Biocojugate Chem. 2000, 11, 84-93.
19. Hogg, P. J.; Johnson, S. C.; Bowles, M. R.; Pond, S. M.; Winzor, D. J. Evaluation of Equilibrium Constants for Antigen-Antibody Interaction by Solid-phase Immunoassay: the Binding of Paraquant to Its Elicited Mouse Monoclonal Antibody. Mol. Immunol. 1987, 24, 797-801.
20. Kaminogawa, S.; Hattori, M.; Ando, O.; Kurisaki, J.; Yamauchi, K. Preparation of Monoclonal Antibody against Bovine β-Lactoglobulin and Its Unique Affinity. Agric. Biol. Chem. 1987, 51, 797-802.
21. Kaminogawa, S.; Shimizu, M.; Ametani, A.; Hattori, M.; Ando, O.; Hachimura, S.; Nakamura, Y.; Totsuka, M.; Yamauchi, K. Monoclonal Antibodies as Probes for Monitoring the Denaturation Process of Bovine β-Lactoglobulin. Biochim. Biophys Acta 1989, 998, 50-56.
22. Kitabatake, N.; Cuq, J. L.; Cheftel, J. C. Covalent Binding of Glycosyl Residues to β-Lactoglobulin: Effects on Solubility and Heat Stability. J. Agric. Food Chem. 1985, 33, 125-130.
23. Laemmli, U. K. Cleavage of Structural Proteins during the Assembly of the Head of Bacteriophage T4. Nature 1970, 227, 680-685.
24. Lee, W. Y.; Sehon, A. H.; Åkerblom, E. Suppression of Reaginic Antibodies with Modified Allergens. IV. Induction of Suppressor T cells by Conjugates of Polyethylene Glycol (PEG) and Monomethoxy PEG with Ovalbumin. Int. Arch. Allergy Appl. Immunol. 1981, 64, 100-114.
25. Mattarella, N. L.; Richardson, T. Physicochemical and Functional Properties of Positively Charged Derivatives of Bovine β-Lactoglobulin To Form Positively Charged Proteins. J. Agric. Food Chem. 1983, 31, 972-978.
26. Mattarella, N. L.; Creamer, L. K.; Richardson, T. Amidation or Esterification of Bovine β-Lactoglobulin To Form Positively Charged Proteins. J. Agric. Food Chem. 1983, 31, 968-972.
27. McKenzie, H. A. β-Lactoglobulins. In Milk Proteins: Chemistry and Molecular Biology; McKenzie, H. A., Ed.; Academic Press: New York, 1971; Vol. 2, pp 257-330.
28. Nagasawa, K.; Ohgata, K.; Takahashi, K.; Hattori, M. Role of the Polysaccharide Content and Net Charge on the Emulsifying Properties of β-Lactoglobulin-Carboxymethyl Dextran Conjugates. J. Agric. Food Chem. 1996a, 44, 2538-2543.
29. Nagasawa, K.; Takahashi, K.; Hattori, M. Improved Emulsifying Properties of β-Lactoglobulin by Conjugating with Carboxymethyl Dextran. Food Hydrocolloids 1996b, 10, 63-67.
30. Papiz, M. Z.; Sawyer, L.; Eliopoulos, E. E.; North, A. C. T.; Findlay, J. B. C.; Sivaprasadrao, R.; Jones, T. A.; Newcomer, M. E.; Kraulis, P. J. The Structure of β-Lactoglobulin and Its Similarity to Plasma Retinol-Binding Protein. Nature 1986, 324, 383-385.
31. Pearce, K. N.; Kinsella, J. E. Emulsifying Properties of Proteins: Evaluation of a Turbidimetric Technique. J. Agric. Food Chem. 1978, 26, 716-723.
32. Pérez, M. D.; Calvo, M. Interaction of β-Lactoglobulin with Retinol and Fatty Acids and Its Role as A Possible Biological Function for this Protein. J. Dairy Sci. 1995, 78, 978-988.
33. Pervaiz, S.; Brew, K. Homology of β-Lactoglobulin, Serum Retinol Binding Protein, and Protein HC. Science 1985, 228, 335-337.
34. Shimizu, M.; Saito, M.; Yamauchi, K. Emulsifying and Structural Properties of β-Lactoglobulin at Different pHs. Agric. Biol. Chem. 1985, 49, 189-194.
35. So, T.; Ito, H. O.; Koga, T.; Ueda, T.; Imoto, T. Reduced Immunogenicity of Monomethoxypolyethylene Glycol-modified Lysozyme for Activation of T cells. Immunol. Lett. 1996, 49, 91-97.
36. Spies, J. Milk Allergy. J. Milk Food Technol. 1973, 36, 225-231.
37. Waniska, R. D.; Kinsella, J. E. Foaming and Emulsifying Properties of Glycosylated β-Lactoglobulin. Food Hydrocolloids 1988, 2, 439-449.
38. Winterowd, J. G.; Sandford, P. A.; Chitin and Chitosan. In Food Polysaccharides and Their Applications; Stephan, A. M., Ed.; Dekker: New York, 1995; pp 441-462.