Mutagenesis and evolution of sulfated antibodies using an expanded genetic code

Biochemistry

Volumn 48, Issue 37, 2009, Pages 8891-8898

  Liu, Chang C ^a   Choe, Hyeryun ^b   Farzan, Michael ^c   Smider, Vaughn V ^a   Schultz, Peter G ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b BOSTON CHILDREN S HOSPITAL   (United States)

^c HARVARD MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOACYL; BINDING AFFINITIES; BIOCHEMICAL STUDIES; DIRECTED EVOLUTION; E. COLI; FRAMESHIFT; GENETIC CODE; HEAVY CHAIN; MODIFIED AMINO ACIDS; MODIFIED PROTEINS; POST-TRANSLATIONAL MODIFICATIONS; PROTEIN FUNCTIONS;

AMINATION; AMINES; ANTIBODIES; BINDING ENERGY; ESCHERICHIA COLI; ORGANIC ACIDS;

AMINO ACIDS;

AMINO ACID TRANSFER RNA LIGASE; GLYCOPROTEIN GP 120; PROTEIN ANTIBODY; PROTEIN ANTIBODY 412D; TYROSINE SULFATE; UNCLASSIFIED DRUG;

ANTIBODY LIBRARY; ARTICLE; BACTERIOPHAGE; BINDING AFFINITY; CONTROLLED STUDY; ESCHERICHIA COLI; GENETIC CODE; MOLECULAR EVOLUTION; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN PROCESSING; SITE DIRECTED MUTAGENESIS; SULFATION;

ANTIBODIES, BACTERIAL; BINDING SITES, ANTIBODY; DIRECTED MOLECULAR EVOLUTION; GENETIC CODE; HIV ENVELOPE PROTEIN GP120; HUMANS; IMMUNOGLOBULIN FAB FRAGMENTS; MUTAGENESIS, SITE-DIRECTED; PROTEIN PROCESSING, POST-TRANSLATIONAL; TYROSINE;

ESCHERICHIA COLI;

EID: 70349095953     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi9011429     Document Type: Article

References (29)

1. Xie, J., and Schultz, P. G. (2005) Adding amino acids to the genetic repertoire. Curr. Opin. Chem. Biol. 9, 548-554. (Pubitemid 41612181)
2. Bernimoulin, M. P., Zeng, X. L., Abbal, C., Giraud, S., Martinez, M., Michielin, O., Schapira, M., and Spertini, O. (2003) Molecular basis of leukocyte rolling on PSGL-1. Predominant role of core-2 O-glycans and of tyrosine sulfate residue 51. J. Biol. Chem. 278, 37-47. (Pubitemid 36043541)
3. Pouyani, T., and Seed, B. (1995) PSGL-1 recognition of P-selectin is controlled by a tyrosine sulfation consensus at the PSGL-1 amino terminus. Cell 83, 333-343.
4. Fong, A. M., Alam, S. M., Imai, T., Haribabu, B., and Patel, D. D. (2002) CX3CR1 tyrosine sulfation enhances fractalkine-induced cell adhesion. J. Biol. Chem. 277, 19418-19423. (Pubitemid 34967450)
5. Farzan, M., Babcock, G. J., Vasilieva, N., Wright, P. L., Kiprilov, E., Mirzabekov, T., and Choe, H. (2002) The role of post-translational modifications of the CXCR4 amino terminus in stromal-derived factor 1 alpha association and HIV-1 entry. J. Biol. Chem. 277, 29484-29489. (Pubitemid 41079234)
6. Kehoe, J. W., and Bertozzi, C. R. (2000) Tyrosine sulfation: a modulator of extracellular protein-protein interactions. Chem. Biol. 7, R57-61.
7. Preobrazhensky, A. A., Dragan, S., Kawano, T., Gavrilin, M. A., Gulina, I. V., Chakravarty, L., and Kolattukudy, P. E. (2000) Monocyte chemotactic protein-1 receptor CCR2B is a glycoprotein that has tyrosine sulfation in a conserved extracellular N-terminal region. J. Immunol. 165, 5295-5303. (Pubitemid 30809463)
8. Dorfman, T., Moore, M. J., Guth, A. C., Choe, H., and Farzan, M. (2006) A tyrosine-sulfated peptide derived from the heavy-chain CDR3 region of an HIV-1-neutralizing antibody binds gp120 and inhibits HIV-1 infection. J. Biol. Chem. 281, 28529-28535. (Pubitemid 44506995)
9. Farzan, M., Mirzabekov, T., Kolchinsky, P., Wyatt, R., Cayabyab, M., Gerard, N. P., Gerard, C., Sodroski, J., and Choe, H. (1999) Tyrosine sulfation of the amino terminus of CCR5 facilitates HIV-1 entry. Cell 96, 667-676. (Pubitemid 29122809)
10. Liu, C. C., Brustad, E., Liu, W., and Schultz, P. G. (2007) Crystal structure of a biosynthetic sulfo-hirudin complexed to thrombin. J. Am. Chem. Soc. 129, 10648-10649. (Pubitemid 350067462)
11. Veldkamp, C. T., Seibert, C., Peterson, F. C., De la Cruz, N. B., Haugner, J. C., Basnet, H., Sakmar, T. P., and Volkman, B. F. (2008) Structural basis of CXCR4 sulfotyrosine recognition by the chemokine SDF-1/CXCL12. Sci. Signaling 1, ra4.
12. Huang, C. C., Lam, S. N., Acharya, P., Tang, M., Xiang, S. H., Hussan, S. S., Stanfield, R. L., Robinson, J., Sodroski, J., Wilson, I. A., Wyatt, R., Bewley, C. A., and Kwong, P. D. (2007) Structures of the CCR5Nterminus and of a tyrosine-sulfated antibody with HIV-1 gp120 and CD4. Science (New York) 317, 1930-1934. (Pubitemid 47509439)
13. Choe, H., Li, W., Wright, P. L., Vasilieva, N., Venturi, M., Huang, C. C., Grundner, C., Dorfman, T., Zwick, M. B., Wang, L., Rosenberg, E. S., Kwong, P. D., Burton, D. R., Robinson, J. E., Sodroski, J. G., and Farzan, M. (2003) Tyrosine sulfation of human antibodies contributes to recognition of the CCR5 binding region of HIV-1 gp120. Cell 114, 161-170. (Pubitemid 36936910)
14. Choe, H., Moore, M. J., Owens, C. M., Wright, P. L., Vasilieva, N., Li, W., Singh, A. P., Shakri, R., Chitnis, C. E., and Farzan, M. (2005) Sulphated tyrosines mediate association of chemokines and Plasmodium vivax Duffy binding protein with the Duffy antigen/receptor for chemokines (DARC). Mol. Microbiol. 55, 1413-1422. (Pubitemid 40342069)
15. Hans, D., Pattnaik, P., Bhattacharyya, A., Shakri, A. R., Yazdani, S. S., Sharma, M., Choe, H., Farzan, M., and Chitnis, C. E. (2005) Mapping binding residues in the Plasmodium vivax domain that binds Duffy antigen during red cell invasion. Mol. Microbiol. 55, 1423-1434. (Pubitemid 40342070)
16. Seibert, C., and Sakmar, T. P. (2008) Toward a framework for sulfoproteomics: synthesis and characterization of sulfotyrosine-containing peptides. Biopolymers 90, 459-477.
17. Choe, H., and Farzan, M. (2009) Tyrosine sulfation of HIV-1 coreceptors and other chemokine receptors. Methods Enzymol. 461, 147-170.
18. Liu, C. C., and Schultz, P. G. (2006) Recombinant expression of selectively sulfated proteins in Escherichia coli. Nat. Biotechnol. 24, 1436-1440. (Pubitemid 44722108)
19. Liu, C. C., Cellitti, S. E., Geierstanger, B. H., Schultz, P. G. (2009) Efficient expression of tyrosine-sulfated proteins in E. coli using an expanded genetic code, submitted.
20. Liu, C. C., Mack, A. V., Tsao, M. L., Mills, J. H., Lee, H. S., Choe, H., Farzan, M., Schultz, P. G., and Smider, V. V. (2008) Protein evolution with an expanded genetic code. Proc. Natl. Acad. Sci. U.S.A. 105, 17688-17693.
21. Moore, K. L. (2003) The biology and enzymology of protein tyrosine O-sulfation. J. Biol. Chem. 278, 24243-24246.
22. Rondot, S., Koch, J., Breitling, F., and Dubel, S. (2001) A helper phage to improve single-chain antibody presentation in phage display. Nat. Biotechnol. 19, 75-78. (Pubitemid 32051961)
23. Broders, O., Breitling, F., and Dubel, S. (2003) Hyperphage. Improving antibody presentation in phage display. Methods Mol. Biol. 205, 295-302.
24. Xie, J., Supekova, L., and Schultz, P. G. (2007) A genetically encoded metabolically stable analogue of phosphotyrosine in Escherichia coli. ACS Chem. Biol. 2, 474-478. (Pubitemid 350001544)
25. Neumann, H., Hazen, J. L., Weinstein, J., Mehl, R. A., and Chin, J. W. (2008) Genetically encoding protein oxidative damage. J. Am. Chem. Soc. 130, 4028-4033.
26. Cormier, E. G., Persuh, M., Thompson, D. A., Lin, S. W., Sakmar, T. P., Olson, W. C., and Dragic, T. (2000) Specific interaction of CCR5 amino-terminal domain peptides containing sulfotyrosines with HIV-1 envelope glycoprotein gp120. Proc. Natl. Acad. Sci. U.S.A. 97, 5762-5767. (Pubitemid 30367472)
27. Albertini, S., Chetelat, A. A., Miller, B., Muster, W., Pujadas, E., Strobel, R., and Gocke, E. (1995) Genotoxicity of 17 gyrase- and four mammalian topoisomerase II-poisons in prokaryotic and eukaryotic test systems. Mutagenesis 10, 343-351.
28. Bossi, L. (1983) Context effects: translation of UAG codon by suppressor tRNA is affected by the sequence following UAG in the message. J. Mol. Biol. 164, 73-87.
29. Stone, S. R., and Hofsteenge, J. (1986) Kinetics of the inhibition of thrombin by hirudin. Biochemistry 25, 4622-4628.