Site-selective lysine modification of native proteins and peptides via kinetically controlled labeling

Bioconjugate Chemistry

Volumn 23, Issue 3, 2012, Pages 500-508

  Chen, Xi ^a,b   Muthoosamy, Kasturi ^a   Pfisterer, Anne ^c   Neumann, Boris ^d   Weil, Tanja ^a,b,c  

^a UNIVERSITY OF ULM   (Germany)

^b NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

^c MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

^d PROTEOME FACTORY AG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; KINETICS; PH; RECOMBINANT PROTEINS;

ETHYNYL; KINETICALLY CONTROLLED; LABELINGS; LYSINE MODIFICATION; LYSINE RESIDUES; NATIVE PROTEINS; PEPTIDE HORMONES; RNASE A; SELECTIVE MODIFICATION; SITE SELECTIVE;

PEPTIDES;

ALKYNYL GROUP; AZIDE; COUMARIN DERIVATIVE; LYSINE; LYSOZYME; PEPTIDE DERIVATIVE; REAGENT; RIBONUCLEASE A; SOMATOSTATIN;

ARTICLE; BIOTINYLATION; CHEMICAL REACTION KINETICS; CLICK CHEMISTRY; CONJUGATION; PH; PROTEIN FOLDING; PROTEIN MODIFICATION; QUANTUM YIELD; TEMPERATURE DEPENDENCE;

EID: 84863376953     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc200556n     Document Type: Article

References (29)

1. Francis, M. B. and Carrico, I. S. (2010) New frontiers in protein bioconjugation Curr. Opin. Chem. Biol. 14, 771-773
2. Harris, J. M. and Chess, R. B. (2003) Effect of PEGylation on pharmaceuticals Nat. Rev. Drug. Discovery 2, 214-221 (Pubitemid 37361666)
3. Bell, S. J., Fam, C. M., Chlipala, E. A., Carlson, S. J., Lee, J. I., Rosendahl, M. S., Doherty, D. H., and Cox, G. N. (2008) Enhanced circulating half-life and antitumor activity of a site-specific PEGylated interferon-α protein therapeutic Bioconjugate Chem. 19, 299-305 (Pubitemid 351213862)
4. Floyd, N., Vijayakrishnan, B., Koeppe, J. R., and Davis, B. G. (2009) Thiyl glycosylation of olefinic proteins: S-linked glycoconjugate synthesis Angew. Chem., Int. Ed. Engl. 48, 7798-7802
5. Bagshaw, C. R. and Cherny, D. (2006) Blinking fluorophores: what do they tell us aboutprotein dynamics? Biochem. Soc. Trans. 979-982 (Pubitemid 44796464)
6. Michalet, X., Weiss, S., and Jäger, M. (2006) Single-molecule fluorescence studies of protein folding and conformational dynamics Chem. Rev. 106, 1785-1813 (Pubitemid 43792781)
7. Royer, C. A. (2006) Probing protein folding and conformational transitions with fluorescence Chem. Rev. 106, 1769-1784 (Pubitemid 43792780)
8. Hucknall, A., Kim, D. -H., Rangarajan, S., Hill, R. T., Reichert, W. M., and Chilkoti, A. (2009) Simple fabrication of antibody microarrays on nonfouling polymer brushes with femtomolar sensitivity for protein analytes in serum and blood Adv. Mater. 21, 1968-1971
9. Chen, M. -L., Adak, A. -K., Yeh, N. -C., Yang, W. -B., Chuang, Y. -J., Wong, C. -H., Hwang, K. -C., Reuben, J. -R., Hwu, J. -R., Hsieh, S. -L., and Lin, C. -C. (2008) Fabrication of an oriented Fc-fused lectin microarray through boronate formation Angew. Chem., Int. Ed. Engl. 47, 8627-8630
10. Löwik, D. W. P. M, Shklyarevskiy, I. O., Ruizendaal, L., Christianen, P. C. M., Maan, J. C., and van Hest, J. C. M. (2007) A highly ordered material from magnetically aligned peptide amphiphile nanofiber assemblies Adv. Mater. 19, 1191-1195 (Pubitemid 46942246)
11. Chalker, J. M., Bernardes, G. J. L., Lin, Y. A., and Davis, B. J. (2009) Chemical modification of proteins at cysteine: opportunities in chemistry and biology Chem. Asian J. 4, 630-640
12. Smith, M. E. B., Schumacher, F. F., Ryan, C. P., Tedaldi, L. M., Papaioannou, D., Waksman, G., Caddick, S., and Baker, J. R. (2010) Protein modification, bioconjugation, and disulfide bridging using bromomaleimides J. Am. Chem. Soc. 132, 1960-1965
13. Ryan, C. P., Smith, M. E. B., Schumacher, F. F., Grohmann, D., Papaioannou, D., Waksman, G., Werner, F., Baker, J. R., and Caddick, S. (2011) Tunable reagents for multi-functional bioconjugation: reversible or permanent chemical modification of proteins and peptides by control of maleimide hydrolysis Chem. Commun. 47, 5452-5454
14. Tanrikulu, C., Schmitt, E., Mechulam, Y., Goddard, W. A., III, and Tirrell, D. A. (2009) Discovery of escherichia coli methionyl-tRNA synthetase mutants for efficient labeling of proteins with azidonorleucine in vivo Proc. Natl. Acad. Sci. U.S.A. 106, 15285-15290
15. Kiick, K. L., van Hest, J. C., and Tirrell, D. A. (2000) Expanding the scope of protein biosynthesis by altering the methionyl-tRNA synthetase activity of a bacterial expression host Angew. Chem., Int. Ed. Engl. 39, 2148-2152 (Pubitemid 30435615)
16. Xie, J. and Schultz, P. G. (2006) A chemical toolkit for proteins - an expanded genetic code Nat. Rev. Mol. Cell. Biol. 7, 775-782 (Pubitemid 44450461)
17. Hackenberger, C. P. R and Schwarzer, D. (2008) Chemoselective ligation and modification strategies for peptides and proteins Angew. Chem., Int. Ed. Engl. 47, 10030-10074
18. Sletten, E. M. and Bertozzi, C. R. (2009) Bioorthogonal chemistry: Fishing for selectivity in a sea of functionality Angew. Chem., Int. Ed. Engl. 48, 6974-6998
19. I-catalyzed 1,2,3-triazole formation and its implementation in protein microarray fabrication Angew. Chem., Int. Ed. Engl. 45, 4286-4290 (Pubitemid 44105634)
20. Saxon, E. and Bertozzi, C. R. (2000) Cell surface engineering by a modified Staudinger reaction Science 287, 2007-2010 (Pubitemid 30158675)
21. +-based CO releasing molecules (tpm = tris(pyrazolyl)methane) Dalton Trans. 4292-4298
22. Sunbul, M. and Yin, J. (2009) Site specific protein labeling by enzymatic posttranslational modification Org. Biomol. Chem. 7, 3361-3371
23. Chen, Z., Popp, B. V., Bovet., C. L., and Ball, Z. T. (2011) Site-specific protein modification with a dirhodium metallopeptide catalyst ACS Chem. Biol. 6, 920-925
24. Shaunak, S., Godwin, A., Choi, J. -W., Balan, S., Pedone, E., Vijayarangam, D., Heidelberger, S., Teo, I., Zloh, M., and Brocchini, S. (2006) Site-specific PEGylation of native disulfide bonds in therapeutic proteins Nat. Chem. Biol. 2, 312-313 (Pubitemid 43787211)
25. Brocchini, S., Balan, S., Godwin, A., Choi, J. -W., Zloh, M., and Shaunak, S. (2006) PEGylation of native disulfide bonds in proteins Nat. Protoc. 1, 2241-2252
26. Gilmore, J. M., Scheck, R. A., Esser-Kahn, A. P., Joshi, N. S., and Francis, M. B. (2006) N-Terminal protein modification through a biomimetic transamination reaction Angew. Chem., Int. Ed. Engl. 45, 5307-5311 (Pubitemid 44289366)
27. Ardelt, W., Shogen, K., and Darzynkiewicz, Z. (2008) Onconase and amphinase, the antitumor ribonucleases from rana pipiens oocytes Curr. Pharm. Biotechnol. 9, 215-225 (Pubitemid 352024698)
28. Henrikson, K. P., Allen, S. H. G., and Maloy, W. L. (1979) An avidin monomer affinity column for the purification of biotin-containing enzymes Anal. Biochem. 94, 366-370
29. Thompson, M. J. and Goldstein, R. A. (1996) Predicting solvent accessibility: higher accuracy using Bayesian statistics and optimized residue substitution classes Proteins 25, 38-47 (Pubitemid 26156340)