Split Spy0128 as a potent scaffold for protein cross-linking and immobilization

Bioconjugate Chemistry

Volumn 24, Issue 2, 2013, Pages 242-250

  Abe, Hiroki ^a   Wakabayashi, Rie ^a   Yonemura, Hiroaki ^a,b   Yamada, Sunao ^a,b   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

ADDITION REACTIONS; CROSSLINKING; ENERGY TRANSFER; FORSTER RESONANCE ENERGY TRANSFER; SCAFFOLDS (BIOLOGY);

AUTOCATALYTIC; BIO-CONJUGATION; COVALENT COMPLEX; CROSS-LINKING TECHNIQUES; IMMOBILISATION; ISOPEPTIDES; N TERMINUS; PROPERTY; PROTEIN CROSSLINKING; SITE-SPECIFIC;

PROTEINS;

CYSTEINE; GREEN FLUORESCENT PROTEIN; PILIN; PILIN PROTEIN SPY0128; SCAFFOLD PROTEIN; UNCLASSIFIED DRUG;

AMINO TERMINAL SEQUENCE; ARTICLE; BACTERIUM CONJUGATION; BIOCONJUGATION; CATALYSIS; CONJUGATION; CONTROLLED STUDY; COVALENT BOND; CROSS LINKING; ENZYME RECONSTITUTION; FLUORESCENCE RESONANCE ENERGY TRANSFER; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; MICHAEL ADDITION; MUTANT; NONHUMAN; PROTEIN CROSS LINKING; PROTEIN IMMOBILIZATION; SITE SPECIFIC CROSS LINKING TECHNIQUE; STREPTOCOCCUS PYOGENES; VALIDATION PROCESS;

EID: 84874035250     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc300606b     Document Type: Article

References (33)

1. Stephanopoulos, N. and Francis, M. B. (2011) Choosing an effective protein bioconjugation strategy Nat. Chem. Biol. 7, 876-884
2. Sletten, E. M. and Bertozzi, C. R. (2009) Bioorthogonal chemistry: Fishing for selectivity in a sea of functionality Angew. Chem., Int. Ed. 48, 6974-6998
3. Sunbul, M. and Yin, J. (2009) Site specific protein labeling by enzymatic posttranslational modification Org. Biomol. Chem. 7, 3361-3371
4. Fontana, A., Spolaore, B., Mero, A., and Veronese, F. M. (2008) Site-specific modification and PEGylation of pharmaceutical proteins mediated by transglutaminase Adv. Drug Delivery Rev. 60, 13-28
5. Lin, C. W. and Ting, A. Y. (2006) Transglutaminase-catalyzed site-specific conjugation of small-molecule probes to proteins in vitro and on the surface of living cells J. Am. Chem. Soc. 128, 4542-4543
6. Abe, H., Goto, M., and Kamiya, N. (2011) Protein lipidation catalyzed by microbial transglutaminase Chem.-Eur. J. 17, 14004-14008
7. Popp, M. W., Antos, J. M., Grotenbreg, G. M., Spooner, E., and Ploegh, H. L. (2007) Sortagging: a versatile method for protein labeling Nat. Chem. Biol. 3, 707-708
8. Popp, M. W. L. and Ploegh, H. L. (2011) Making and breaking peptide bonds: Protein engineering using sortase Angew. Chem., Int. Ed. 50, 5024-5032
9. Muir, T. W. (2003) Semisynthesis of proteins by expressed protein ligation Annu. Rev. Biochem. 72, 249-289
10. Mootz, H. D. (2009) Split inteins as versatile tools for protein semisynthesis ChemBioChem 10, 2579-2589
11. Kang, H. J. and Baker, E. N. (2011) Intramolecular isopeptide bonds: protein crosslinks built for stress? Trends Biochem. Sci. 36, 227-235
12. Kang, H. J. and Baker, E. N. (2012) Structure and assembly of Gram-positive bacterial pili: unique covalent polymers Curr. Opin. Struct. Biol. 22, 200-207
13. Kang, H. J., Coulibaly, F., Clow, F., Proft, T., and Baker, E. N. (2007) Stabilizing isopeptide bonds revealed in Gram-positive bacterial pilus structure Science 318, 1625-1628
14. Zakeri, B. and Howarth, M. (2010) Spontaneous intermolecular amide bond formation between side chains for irreversible peptide targeting J. Am. Chem. Soc. 132, 4526-4527
15. Hirakawa, H., Kamiya, N., Tanaka, T., and Nagamune, T. (2007) Intramolecular electron transfer in a cytochrome P450cam system with a site-specific branched structure Protein Eng., Des. Sel. 20, 453-459
16. Hirakawa, H. and Nagamune, T. (2010) Molecular assembly of P450 with ferredoxin and ferredoxin reductase by fusion to PCNA ChemBioChem 11, 1517-1520
17. You, C., Myung, S., and Zhang, Y.-H. P. (2012) Facilitated substrate channeling in a self-assembled trifunctionalenzyme complex Angew. Chem., Int. Ed. 51, 1-5
18. Takeda, S., Kamiya, N., Arai, R., and Nagamune, T. (2001) Design of an artificial light-harvesting unit by protein engineering: Cytochrome b(562)-green fluorescent protein chimera Biochem. Biophys. Res. Commun. 289, 299-304
19. Tanaka, Y., Tsuruda, Y., Nishi, M., Kamiya, N., and Goto, M. (2007) Exploring enzymatic catalysis at a solid surface: a case study with transglutaminase-mediated protein immobilization Org. Biomol. Chem. 5, 1764-1770
20. Tsien, R. Y. (1998) The green fluorescent protein Annu. Rev. Biochem. 67, 509-544
21. Subach, O. M., Gundorov, I. S., Yoshimura, M., Subach, F. V., Zhang, J. H., Gruenwald, D., Souslova, E. A., Chudakov, D. M., and Verkhusha, V. V. (2008) Conversion of red fluorescent protein into a bright blue probe Chem. Biol. 15, 1116-1124
22. Yonemura, H., Harada, S., Moribe, S., Yamada, S., Nakamura, H., Fujiwara, Y., and Tanimoto, Y. (2006) Magnetic field effects and time-resolved EPR studies on photogenerated biradical from intramolecular electron transfer reactions in zinc-tetraphenylporphyrin-C-60 linked compounds: contribution of relaxation mechanism due to spin-spin relaxation Mol. Phys. 104, 1559-1572
23. Kaiser, E., Colescot., Rl, Bossinge., Cd, and Cook, P. I. (1970) Color test for detection of free terminal amino groups in solid-phase synthesis of peptides Anal. Biochem. 34, 595-598
24. Giglione, C., Boularot, A., and Meinnel, T. (2004) Protein N-terminal methionine excision Cell Mol. Life Sci. 61, 1455-1474
25. Turro, N. J., Ramamurthy, V., and Scaiano, J. C. (2010) Energy Transfer and Electron Transfer, Modern molecular photochemistry of organic molecules, Chapter 7, pp 391-406, University Science Books, Sausalito, CA.
26. Subach, O. M., Malashkevich, V. N., Zencheck, W. D., Morozova, K. S., Piatkevich, K. D., Almo, S. C., and Verkhusha, V. V. (2010) Structural characterization of acylimine-containing blue and red chromophores in mTagBFP and TagRFP fluorescent proteins Chem. Biol. 17, 333-341
27. Wong, L. S., Khan, F., and Micklefield, J. (2009) Selective covalent protein immobilization: strategies and applications Chem. Rev. 109, 4025-4053
28. Kwon, Y., Coleman, M. A., and Camarero, J. A. (2006) Selective immobilization of proteins onto solid supports through split-intein-mediated protein trans-splicing Angew. Chem., Int. Ed. 45, 1726-1729
29. Weinrich, D., Lin, P. C., Jonkheijm, P., Nguyen, U. T. T., Schroder, H., Niemeyer, C. M., Alexandrov, K., Goody, R., and Waldmann, H. (2010) Oriented immobilization of farnesylated proteins by the thiol-ene reaction Angew. Chem., Int. Ed. 49, 1252-1257
30. Cheung, C. L., Camarero, J. A., Woods, B. W., Lin, T. W., Johnson, J. E., and De Yoreo, J. J. (2003) Fabrication of assembled virus nanostructures on templates of chemoselective linkers formed by scanning probe nanolithography J. Am. Chem. Soc. 125, 6848-6849
31. Kang, H. J. and Baker, E. N. (2009) Intramolecular isopeptide bonds give thermodynamic and proteolytic stability to the major pilin protein of Streptococcus pyogenes J. Biol. Chem. 284, 20729-20737
32. Hu, X. Q., Hu, H., Melvin, J. A., Clancy, K. W., McCafferty, D. G., and Yang, W. T. (2011) Autocatalytic intramolecular isopeptide bond formation in Gram-positive bacterial pili: A QM/MM simulation J. Am. Chem. Soc. 133, 478-485
33. Zakeri, B., Fierer, J. O., Celik, E., Chittock, E. C., Schwarz-Linek, U., Moy, V. T., and Howarth, M. (2012) Peptide tag forming a rapid covalent bond to a protein, through engineering a bacterial adhesin Proc. Natl. Acad. Sci. U.S.A. 109, E690-E697