Peroxidase induced oligo-tyrosine cross-links during polymerization of α-lactalbumin

Biochimica et Biophysica Acta - Proteins and Proteomics

Volumn 1854, Issue 12, 2015, Pages 1898-1905

  Dhayal, Surender Kumar ^a   Sforza, Stefano ^a,b   Wierenga, Peter A ^a   Gruppen, Harry ^a  

^a WAGENINGEN UNIVERSITY   (Netherlands)

^b UNIVERSITY OF PARMA   (Italy)

Author keywords

Dityrosine; Enzymatic oxidation; Protein oxidation; Protein polymers; Tetratyrosine; Trityrosine

Indexed keywords

ALPHA LACTALBUMIN; AMIDE; AMINO ACID; ANGIOTENSIN; HORSERADISH PEROXIDASE; HYDROGEN PEROXIDE; MONOMER; N ACETYLTYROSINAMIDE; NANOPARTICLE; OLIGOMER; OLIGOTYROSINE; PROTEIN HYDROLYSATE; TYROSINE; UNCLASSIFIED DRUG; BIOPOLYMER; CROSS LINKING REAGENT; LACTALBUMIN; PEROXIDASE;

ARTICLE; CHEMICAL MODEL; CROSS LINKING; ENZYME ACTIVITY; HYDRODYNAMICS; HYDROLYSIS; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; MOLECULAR WEIGHT; POLYMERIZATION; PRIORITY JOURNAL; SUBSTRATE CONCENTRATION; TANDEM MASS SPECTROMETRY; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY;

BIOPOLYMERS; CROSS-LINKING REAGENTS; LACTALBUMIN; PEROXIDASE; TYROSINE;

EID: 84944097664     PISSN: 15709639     EISSN: 18781454     Source Type: Journal    
DOI: 10.1016/j.bbapap.2015.08.001     Document Type: Article

References (24)

1. J. Buchert, D.E. Cura, H. Ma, C. Gasparetti, E. Monogioudi, G. Faccio, M. Mattinen, H. Boer, R. Partanen, E. Selinheimo, R. Lantto, and K. Kruus Crosslinking food proteins for improved functionality Annu. Rev. Food Sci. Technol. 1 2010 113 138
2. E. Özrenk The use of transglutaminase in dairy products Int. J. Dairy Technol. 59 1 2006 1 7
3. T. Heck, G. Faccio, M. Richter, and L. Thöny-Meyer Enzyme-catalyzed protein crosslinking Appl. Microbiol. Biotechnol. 97 2 2013 461 475
4. A.M. Azevedo, V.C. Martins, D.M.F. Prazeres, V. Vojinovic, J.M.S. Cabral, L.P. Fonseca, and M.R. El-Gewely Horseradish Peroxidase: a Valuable Tool in Biotechnology Vol. 9 2003 Elsevier
5. T. DiMarco, and C. Giulivi Current analytical methods for the detection of dityrosine, a biomarker of oxidative stress, in biological samples Mass Spectrom. Rev. 26 1 2007 108 120
6. D.A. Malencik, and S.R. Anderson Dityrosine formation in calmodulin: cross-linking and polymerization catalyzed by arthromyces peroxidase Biochemistry 35 14 1996 4375 4386
7. W.H. Heijnis, H.L. Dekker, L.J. de Koning, P.A. Wierenga, A.H. Westphal, C.G. de Koster, H. Gruppen, and W.J.H. van Berkel Identification of the peroxidase-generated intermolecular dityrosine cross-link in bovine α-lactalbumin J. Agric. Food Chem. 59 1 2010 444 449
8. G. Oudgenoeg Peroxidase Catalyzed Conjugation of Peptides, Proteins and Polysaccharides via Endogenous and Exogenous Phenols PhD thesis 2004 Wageningen University Wageningen, The Netherlands
9. Y. Saricay, P. Wierenga, and R. de Vries Nanostructure development during peroxidase catalysed cross-linking of α-lactalbumin Food Hydrocoll. 33 2 2013 280 288
10. T. Fukuoka, Y. Tachibana, H. Tonami, H. Uyama, and S. Kobayashi Enzymatic polymerization of tyrosine derivatives. peroxidase- and protease-catalyzed synthesis of polytyrosines with different structures Biomacromolecules 3 4 2002 768 774
11. S.O. Andersen The cross-links in resilin identified as dityrosine and trityrosine Biochim. Biophys. Acta, Gen. Subj. 93 1 1964 213 215
12. F. LaBella, F. Keeley, S. Vivian, and D. Thornhill Evidence for dityrosine in elastin Biochem. Biophys. Res. Commun. 26 6 1967 748 753
13. L. Lopez-Llorca, and S. Fry Dityrosine, trityrosine and tetratyrosine, potential cross-links in structural proteins of plant-parasitic nematodes Nematologica 35 2 1989 165 179
14. F. Fenaille, V. Parisod, J. Vuichoud, J. Tabet, and P.A. Guy Quantitative determination of dityrosine in milk powders by liquid chromatography coupled to tandem mass spectrometry using isotope dilution J. Chromatogr. A 1052 1-2 2004 77 84
15. D. Fujimoto, K. Horiuchi, and M. Hirama Isotrityrosine, a new crosslinking amino acid isolated from ascaris cuticle collagen Biochem. Biophys. Res. Commun. 99 2 1981 637 643
16. F. Hanft, and P. Koehler Quantitation of dityrosine in wheat flour and dough by liquid chromatography-tandem mass spectrometry J. Agric. Food Chem. 53 7 2005 2418 2423
17. S.K. Dhayal, H. Gruppen, R. de Vries, and P.A. Wierenga Controlled formation of protein nanoparticles by enzymatic cross-linking of α-lactalbumin with horseradish peroxidase Food Hydrocoll. 36 2014 53 59
18. W.H. Heijnis, P.A. Wierenga, W.J.H. van Berkel, and H. Gruppen Directing the oligomer size distribution of peroxidase-mediated cross-linked bovine α-lactalbumin J. Agric. Food Chem. 58 9 2010 5692 5697
19. H. Pichorner, D. Metodiewa, and C.C. Winterbourn Generation of superoxide and tyrosine peroxide as a result of tyrosyl radical scavenging by glutathione Arch. Biochem. Biophys. 323 2 1995 429 437
20. B.J.H. Kuipers, and H. Gruppen Prediction of molar extinction coefficients of proteins and peptides using UV absorption of the constituent amino acids at 214 nm to enable quantitative reverse phase high-performance liquid chromatography mass spectrometry analysis J. Agric. Food Chem. 55 14 2007 5445 5451
21. T. Michon, M. Chenu, N. Kellershon, M. Desmadril, and J. Gueguen Horseradish peroxidase oxidation of tyrosine-containing peptides and their subsequent polymerization: a kinetic study Biochemistry 36 28 1997 8504 8513
22. S. Podzimek Light Scattering, Size Exclusion Chromatography and Asymmetric Flow Field Flow Fractionation 2011 John Wiley & Sons Hoboken, NJ, USA
23. C.E. Lyon, E.S. Suh, C.M. Dobson, and P.J. Hore Probing the exposure of tyrosine and tryptophan residues in partially folded proteins and folding intermediates by CIDNP pulse-labeling J. Am. Chem. Soc. 124 44 2002 13018 13024
24. Y. Saricay, P.A. Wierenga, and R. de Vries Changes in protein conformation and surface hydrophobicity upon peroxidase-catalyzed cross-linking of apo-lactalbumin J. Agric. Food Chem. 62 38 2014 9345 9352