Site-specific protein cross-linking by peroxidase-catalyzed activation of a tyrosine-containing peptide tag

Bioconjugate Chemistry

Volumn 22, Issue 1, 2011, Pages 74-81

  Minamihata, Kosuke ^a   Goto, Masahiro ^a,b   Kamiya, Noriho ^a,b  

^a Grad Sch Eng   (Japan)

^b KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CROSSLINKING; DIMERS; ESCHERICHIA COLI; PEPTIDES; PHOSPHATASES;

COUPLING REACTION; CROSS LINKING; HORSE-RADISH PEROXIDASE; MODIFICATION METHODS; ONE-ELECTRON OXIDATION; PEPTIDE TAGS; PROTEIN CROSSLINKING; PROTEIN MODIFICATIONS; SITE-SPECIFIC; TYROSINE RESIDUES;

AMINO ACIDS;

ALKALINE PHOSPHATASE; HORSERADISH PEROXIDASE; HYDROGEN PEROXIDE; THROMBIN; TYROSINE;

AMINO ACID SEQUENCE; ARTICLE; CARBOXY TERMINAL SEQUENCE; CATALYSIS; ENZYME ACTIVATION; ENZYME ACTIVITY; ENZYME SPECIFICITY; ENZYME SUBSTRATE; ESCHERICHIA COLI; FLUORESCENCE SPECTROSCOPY; NONHUMAN; PROTEIN CROSS LINKING; PROTEIN EXPRESSION; PROTEIN MODIFICATION; PROTEIN STRUCTURE;

ARMORACIA RUSTICANA; ESCHERICHIA COLI;

EID: 78751614082     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc1003982     Document Type: Article

References (47)

1. Mian, I. S., Bradwell, A. R., and Olson, A. J. (1991) Structure, function and properties of antibody binding sites J. Mol. Biol. 217, 133-151
2. Zemlin, M., Klinger, M., Link, J., Zemlin, C., Bauer, K., Engler, J. A., Schroeder Jr, H. W., and Kirkham, P. M. (2003) Expressed murine and human CDR-H3 intervals of equal length exhibit distinct repertoires that differ in their amino acid composition and predicted range of structures J. Mol. Biol. 334, 733-749
3. Fellouse, F. A., Li, B., Compaan, D. M., Peden, A. A., Hymowitz, S. G., and Sidhu, S. S. (2005) Molecular recognition by a binary code J. Mol. Biol. 348, 1153-1162
4. Koide, A., Gilbreth, R. N., Esaki, K., Tereshko, V., and Koide, S. (2007) High-affinity single-domain binding proteins with a binary-code interface Proc. Natl. Acad. Sci. U.S.A 104, 6632-6637
5. Koide, S. and Sidhu, S. S. (2009) The importance of being tyrosine: lessons in molecular recognition from minimalist synthetic binding proteins ACS Chem. Biol. 4, 325-334
6. Ullrich, A. and Schlessinger, J. (1990) Signal transduction by receptors with tyrosine kinase activity Cell 61, 203-212
7. Andersen, S. O. (1964) The cross-links in resilin identified as dityrosine and trityrosine Biochim. Biophys. Acta 93, 213-215
8. Elvin, C. M., Carr, A. G., Huson, M. G., Maxwell, J. M., Pearson, R. D., Vuocolo, T., Liyou, N. E., Wong, D. C. C., Merritt, D. J., and Dixon, N. E. (2005) Synthesis and properties of crosslinked recombinant pro-resilin Nature 437, 999-1002
9. Raven, D. J., Earland, C., and Little, M. (1971) Occurrence of dityrosine in tussah silk fibroin and keratin Biochim. Biophys. Acta 251, 96-99
10. Fujimoto, D. (1975) Occurrence of dityrosine in cuticlin, a structural protein from Ascaris cuticle Comp. Biochem. Physiol. 51, 205-207
11. LaBella, F., Keeley, F., Vivian, S., and Thornhill, D. (1967) Evidence for dityrosine in elastin Biochem. Biophy. Res. Commun. 26, 748-753
12. Brady, J. D., Sadler, I. H., and Fry, S. C. (1996) Di-isodityrosine, a novel tetrameric derivative of tyrosine in plant cell wall proteins: a new potential cross-link Biochem. J. 315, 323-327
13. Held, M. A., Tan, L., Kamyab, A., Hare, M., Shpak, E., and Kieliszewski, M. J. (2004) Di-isodityrosine is the intermolecular cross-link of isodityrosine-rich extensin analogs cross-linked in vitro J. Biol. Chem. 279, 55474-55482
14. Waykole, P. and Heidemann, E. (1976) Dityrosine in collagen Connect. Tissue Res. 4, 219-222
15. Brown, K. C., Yu, Z., Burlingame, A. L., and Craik, C. S. (1998) Determining protein-protein interactions by oxidative cross-linking of a glycine-glycine-histidine fusion protein Biochemistry 37, 4397-4406
16. Kim, K., Fancy, D. A., Carney, D., and Kodadek, T. (1999) Photoinduced protein cross-linking mediated by palladium porphyrins J. Am. Chem. Soc. 121, 11896-11897
17. Stayner, R. S., Min, D.-J., Kiser, P. F., and Stewart, R. J. (2005) Site-specific cross-linking of proteins through tyrosine hexahistidine tags Bioconjugate Chem. 16, 1617-1623
18. Endrizzi, B. J., Huang, G., Kiser, P. F., and Stewart, R. J. (2006) Specific covalent immobilization of proteins through dityrosine cross-links Langmuir 22, 11305-11310
19. Joshi, N. S., Whitaker, L. R., and Francis, M. B. (2004) A three-component mannich-type reaction for selective tyrosine bioconjugation J. Am. Chem. Soc. 126, 15942-15943
20. Romanini, D. W. and Francis, M. B. (2008) Attachment of peptide building blocks to proteins through tyrosine bioconjugation Bioconjugate Chem. 19, 153-157
21. Guo, H.-M., Minakawa, M., Ueno, L., and Tanaka, F. (2009) Synthesis and evaluation of a cyclic imine derivative conjugated to a fluorescent molecule for labeling of proteins Bioorg. Med. Chem. Lett. 19, 1210-1213
22. Lewandowski, A. T., Small, D. A., Chen, T., Payne, G. F., and Bentley, W. E. (2006) Tyrosine-based "activatable pro-tag": enzyme-catalyzed protein capture and release Biotechnol. Bioeng. 93, 1207-1215
23. Lewandowski, A. T., Yi, H., Luo, X., Payne, G. F., Ghodssi, R., Rubloff, G. W., and Bentley, W. E. (2008) Protein assembly onto patterned microfabricated devices through enzymatic activation of fusion pro-tag Biotechnol. Bioeng. 99, 499-507
24. Wu, H.-C., Shi, X.-W., Tsao, C.-Y., Lewandowski, A. T., Fernandes, R., Hung, C.-W., DeShong, P., Kobatake, E., Valdes, J. J., Payne, G. F., and Bentley, W. E. (2009) Biofabrication of antibodies and antigens via IgG-binding domain engineered with activatable pentatyrosine pro-tag Biotechnol. Bioeng. 103, 231-240
25. Gross, A. J. and Sizer, I. W. (1959) The oxidation of tyramine, tyrosine, and related compounds by peroxidase J. Biol. Chem. 234, 1611-1614
26. Matheis, G. and Whitaker, J. R. (1984) Peroxidase-catalyzed cross linking of proteins J. Protein Chem. 3, 35-48
27. Jacob, J. S., Cistola, D. P., Hsu, F. F., Muzaffar, S., Mueller, D. M., Hazen, S. L., and Heinecke, J. W. (1996) Human phagocytes employ the myeloperoxidase-hydrogen peroxide system to synthesize dityrosine, trityrosine, pulcherosine, and isodityrosine by a tyrosyl radical-dependent pathway J. Biol. Chem. 271, 19950-19956
28. Malencik, D. A. and Anderson, S. R. (1996) Dityrosine formation in calmodulin: cross-linking and polymerization catalyzed by arthromyces peroxidase Biochemistry 35, 4375-4386
29. Michon, T., Chenu, M., Kellershon, N., Desmadril, M., and Guguen, J. (1997) Horseradish peroxidase oxidation of tyrosine-containing peptides and their subsequent polymerization: a kinetic study Biochemistry 36, 8504-8513
30. Souza, J. M., Giasson, B. I., Chen, Q., Lee, V. M.-Y., and Ischiropoulos, H. (2000) Dityrosine cross-linking promotes formation of stable α-synuclein polymers J. Biol. Chem. 275, 18344-18349
31. Oudgenoeg, G., Hilhorst, R., Piersma, S. R., Boeriu, C. G., Gruppen, H., Hessing, M., Voragen, A. G. J., and Laane, C. (2001) Peroxidase-mediated cross-linking of a tyrosine-containing peptide with ferulic acid J. Agric. Food Chem. 49, 2503-2510
32. Fukuoka, T., Tachibana, Y., Tonami, H., Uyama, H., and Kobayashi, S. (2002) Enzymatic polymerization of tyrosine derivatives. peroxidase and protease-catalyzed synthesis of poly(tyrosine)s with different structures Biomacromolecules 3, 768-774
33. Oudgenoeg, G., Dirksen, E., Ingemann, S., Hilhorst, R., Gruppen, H., Boeriu, C. G., Piersma, S. R., van Berkel, W. J. H., Laane, C., and Voragen, A. G. J. (2002) Horseradish peroxidase-catalyzed oligomerization of ferulic acid on a template of a tyrosine-containing tripeptide J. Biol. Chem. 277, 21332-21340
34. Marx, K. A., Lee, J. S., and Sung, C. (2004) Enzymatic copolymerization alters the structure of unpolymerized mixtures of the biomimetic monomers: the amphiphilic decyl ester of L-tyrosine and L-tyrosineamide-an AFM investigation of nano- to micrometer-scale structure differences Biomacromolecules 5, 1869-1876
35. Mattinen, M.-L., Kruus, K., Buchert, J., Nielsen, J. H., Andersen, H. J., and Steffensen, C. L. (2005) Laccase-catalyzed polymerization of tyrosine-containing peptides FEBS J. 272, 3640-3650
36. Mattinen, M.-L., Hellman, M., Permi, P., Autio, K., Kalkkinen, N., and Buchert, J. (2006) Effect of protein structure on laccase-catalyzed protein oligomerization J. Agric. Food Chem. 54, 8883-8890
37. Qin, G., Lapidot, S., Numata, K., Hu, X., Meirovitch, S., Dekel, M., Podoler, I., Shoseyov, O., and Kaplan, D. L. (2009) Expression, cross-linking, and characterization of recombinant chitin binding resilin Biomacromolecules 10, 3227-3234
38. Kobayashi, S., Uyama, H., and Kimura, S. (2001) Enzymatic polymerization Chem. Rev. 101, 3793-3818
39. Fukuoka, T., Uyama, H., and Kobayashi, S. (2004) Polymerization of polyfunctional macromolecules: synthesis of a new class of high molecular weight poly(amino acid)s by oxidative coupling of phenol-containing precursor polymers Biomacromolecules 5, 977-983
40. Kurisawa, M., Chung, J. E., Yang, Y. Y., Gao, S. J., and Uyama, H. (2005) Injectable biodegradable hydrogels composed of hyaluronic acid-tyramine conjugates for drug delivery and tissue engineering Chem. Commun. 4312-4314
41. Tawaki, S., Uchida, Y., Maeda, Y., and Ikeda, I. (2005) HRP-catalyzed polymerization of sugar-based phenols in aqueous organic solvents Carbohydr. Polym. 59, 71-74
42. Xu, P., Uyama, H., Whitten, J. E., Kobayashi, S., and Kaplan, D. L. (2005) Peroxidase-catalyzed in situ polymerization of surface orientated caffeic acid J. Am. Chem. Soc. 127, 11745-11753
43. Jin, R., Hiemstra, C., Zhong, Z., and Feijen, J. (2007) Enzyme-mediated fast in situ formation of hydrogels from dextran-tyramine conjugates Biomaterials 28, 2791-2800
44. Kim, E. E. and Wyckoff, H. W. (1991) Reaction mechanism of alkaline phosphatase based on crystal structures two-metal ion catalysis J. Mol. Biol. 218, 449-464
45. Harms, G. S., Pauls, S. W., Hedstrom, J. F., and Johnson, C. K. (1997) Fluorescence and rotational dynamics of dityrosine J. Fluoresc. 7, 283-292
46. Kamiya, N., Tanaka, T., Suzuki, T., Takazawa, T., Takeda, T., Watanabe, K., and Nagamune, T. (2003) S-peptide as a potent peptidyl linker for protein cross-linking by microbial transglutaminase from Streptomyces mobaraensis Bioconjugate Chem. 14, 351-357
47. Tanaka, T., Kamiya, N., and Nagamune, N. (2004) Peptidyl linkers for protein heterodimerization catalyzed by microbial transglutaminase Bioconjugate Chem. 15, 491-497