Novel method for in vitro O-glycosylation of proteins: Application for bioconjugation

Bioconjugate Chemistry

Volumn 18, Issue 6, 2007, Pages 1912-1918

  Ramakrishnan, Boopathy ^a   Boeggeman, Elizabeth ^a   Qasba, Pradman K ^a  

^a NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBODIES; BIOMOLECULES; ENZYMES; KETONES; LIPOSOMES; PEPTIDES; SUGARS; TARGETED DRUG DELIVERY;

AMINO-ACIDS; BIO-CONJUGATION; E. COLI; FUSION PEPTIDES; GLUTATHIONE S-TRANSFERASES; IN-VITRO; MODELLING SYSTEMS; NOVEL METHODS; O-GLYCOSYLATION; REACTIVE GROUP;

ESCHERICHIA COLI;

AZIDE; GLUTATHIONE TRANSFERASE; IMMUNOLIPOSOME; KETONE; LECTIN; N ACETYLGALACTOSAMINYLTRANSFERASE; PROTEIN; SERINE; THREONINE;

AMINO ACID SEQUENCE; ARTICLE; CARBOXY TERMINAL SEQUENCE; CONJUGATION; ENZYME ENGINEERING; PROTEIN ASSEMBLY; PROTEIN DOMAIN; PROTEIN EXPRESSION; PROTEIN FOLDING; PROTEIN GLYCOSYLATION; PROTEIN TRANSPORT;

BACTERIA (MICROORGANISMS);

EID: 36849018078     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc7002346     Document Type: Article

References (30)

1. Wu, A. M., and Senter, P. D. (2005) Arming antibodies: prospects and challenges for immunoconjugates. Nat. Biotechnol. 23, 1137-1146.
2. Schrama, D., Reisfeld, R. A., and Becker, J. C. (2006) Antibody targeted drugs as cancer therapeutics. Nature Rev. Drug Discovery 5, 147-159.
3. Lambert, J. M. (2005) Drug-conjugated monoclonal antibodiesfor the treatment of Cancer. Curr. Opin. Pharmacol. 5, 543-549.
4. Garnett, M. C. (2001) Targeted drug conjugates: principles and progress. Adv. Drug Delivery Rev. 53, 171-216.
5. Firestone, R. A., Willner, D., Hofstead, S. J., King, H. D., Kaneko, T., Braslawsky, G. R., Greenfield, R. S., Trail, P. A., Lasch, S. J., Henderson, A. J., Casazza, A. M., Hellström, K. E., and Hellström, I. (1996) Synthesis and antitumour activity of the immunoconjugate BR96-Dox. J. Controlled Release 39, 251-259.
6. Dhawan, S. (2002) Design and construction of novel molecular conjugates for signal amplification (I): conjugation of multiple horseradish peroxidase molecules to immunoglobulin via primary amines on lysine peptide chains. Peptides 23, 2091-2098.
7. Stimmel, J. B., Merrill, B. M., Kuyper, L. F., Moxham, C. P., and Hutchins, J. T. (2000) Site-specific conjugation of serine → cysteine variant monoclonal antibodies. J. Biol. Chem. 275, 30445-30450.
8. Albrecht, H., Burke, P. A., Natarajan, A., Xiong, C. Y., and Kalicinsky, M. (2004) Production of soluble scFvs with C-terminal-free thiol for sitespecific conjugation or stable dimeric scFvs on demand. Bioconjugate Chem. 15, 16-26.
9. Saito, G., Swanson, J. A., and Lee, K. D. (2003) Drug delivery strategy utilizing conjugation via reversible disulfide linkages: role and site of cellular reducing activities. Adv. Drug Delivery Rev. 55, 199-215.
10. O'Shanessy, D. J., Dobersen, M. J., and Quarles, R. H. (1984) A novel procedure for labeling immunoglobulins by conjugation to oligosaccharide moieties. Immunol. Lett. 8, 273-277.
11. O'Shanessy, D. J., and Quarles, R. H. (1987) Labeling of the oligosaccharide moieties of immunoglobulins. J. Immunol. Methods 99, 153-161.
12. Rodwell, D., Alvarez, V. L., Lee, C., Lopes, A. D., Goers, J. W. F., King, H. D., Powsner, H. J., and McKearn, T. J. (1986) Site-specific covalent modification of monoclonal antibodies: in vitro and in vivo evaluations. Proc. Natl. Acad. Sci. U.S.A. 83, 2632-2636.
13. Stan, A. C., Radu, D. L., Casares, S., Bona, C. A., and Brumeanu, T-D. (1999) Antineoplastic efficacy of doxorubicin enzymatically assembled on galactose residues of a monoclonal antibody specific for the carcinoembryonic antigen. Cancer Res. 59, 115-121.
14. Qu, Z., Sharkey, R. M., Hansen, H. J., Shih, L. B., Govindan, S. V., Shen, J., Goldenberg, D. M., and Leung, S.-O. (1998) Carbohydrates engineered at antibody constant domains can be used for site-specific conjugation of drugs and chelates. J. Immunol. Methods 213, 131-144.
15. Ramakrishnan, B., and Qasba, P. K. (2002) Structure-based design of beta 1,4-galactosyltransferase I (beta 4Gal-T1) with equally efficient N-acetylgalactosaminyltransferase activity: point mutation broadens beta 4Gal-T1 donor specificity. J. Biol. Chem. 277, 20833-20839.
16. Khidekel, N., Arndt, S., Lamarre-Vincent, N., Lippert, A., Poulin-Kerstien, K. G., Ramakrishnan, B., Qasba, P. K., and Hsieh-Wilson, L. C. (2003) A chemoenzymatic approach toward the rapid and sensitive detection of O-GlcNAc posttranslational modifications. J. Am. Chem. Soc. 125, 16162-16163.
17. Boeggeman, E., Ramakrishnan, B., Kilgore, C., Khidekel, N., Hsieh-Wilson, L. C,, Simpson, J. T,, and Qasba, P. K. (2007) Direct identification of nonreducing GlcNAc residues on N-glycans of glycoproteins using a novel chemoenzymatic method. Bioconjugate Chem. 18, 806-814.
18. Ten Hagen, K. G., Fritz, T. A., and Tabak, L. A. (2003) All in the family: the UDP-GalNAc:polypeptide N-acetylgalactosaminyltransferases. Glycobiology 13, 1R-16R.
19. Dube, D. H., Prescher, J. A., Quang, C. N., and Bertozzi, C. R. (2006) Probing mucin-type O-linked glycosylation in living animals. Proc Natl. Acad. Sci. U.S.A. 103, 4819-4824.
20. Boeggeman, E. E., Ramakrishnan, B., and Qasba, P. K. (2003) The N-terminal stem region of bovine and human betal,4-galactosyltransferase I increases the in vitro folding efficiency of their catalytic domain from inclusion bodies. Protein Expression Purif 30, 219-229.
21. Fritz, T. A., Raman, J., and Tabak, L. A. (2006) Dynamic association between the catalytic and lectin domains of human UDP-GalNAc:polypeptide alpha-N-acetylgalactosaminyltransferase-2. J. Biol. Chem. 281, 8613-8619.
22. Kubota, T., Shiba, T., Sugioka, S., Furukawa, S., Sawaki, H., Kato, R., Wakatsuki, S., and Narimatsu, H. (2006) Structural basis of carbohydrate transfer activity by human UDP-GalNAc: polypeptide alpha-N- acetylgalactosaminyltransferase (pp-GalNAc-T10). J. Mol. Biol. 359, 708-727.
23. Freire, T., Lo-Man, R., Piller, F., Piller, V., Leclerc, C., and Bay, S. (2006) Enzymatic large-scale synthesis of MUC6-Tn glycoconjugates for antitumor vaccination. Glycobiology 16, 390-401.
24. DeFrees, S., Wang, Z. G., Xing, R., Scott, A. E., Wang, B. J., Zopf, D., Gouty, D. L., Sjoberg, E. R., Panneerselvam, K., Brinkman-Van der Linden, E. C., Bayer, R. J., Tarp, M. A., and Clausen, H. (2006) GlycoPEGylation of recombinant therapeutic proteins produced in Escherichia coli. Glycobiology 16, 833-843.
25. Qasba, P. K., Ramakrishnan, B., and Boeggeman, E. (2006) Mutant glycosyltransferases assist in the development of a targeted drug delivery system and contrast agents for MRI. Am. Assoc. Pharm. Soc. J. 8, 190-195.
26. Hollinger, P., and Hudson, P. J. (2005) Engineered antibody fragments and the rise of single domains. Nat. Biotechnol. 23, 1126-1136.
27. Park, J. W., Banz, C. C., and Martin, F. J. (2004) Future directions of liposome- and immunoliposome-based cancer therapeutics. Semin. Oncol. 31, 196-205.
28. Davis, B. G., Lloyd, R. C., and Bryan Jones, J. (1998) Controlled site-selective glycosylation of proteins by a combined site-directed mutagenesis and chemical modification approach. J. Org. Chem. 63, 9614-9615.
29. Kiick, K L., Saxon, E., Tirrell, D. A., and Bertozzi, C. R. (2002) Incorporation of azides into recombinant proteins for chemoselective modification by the Staudinger ligation. Proc. Natl. Acad. Sci. U.S.A. 99, 19-24.
30. Carrico, I. S., Carlson, B. L., and Bertozzi, C. R. (2007) Introducing genetically encoded aldehydes into proteins. Nat. Chem. Biol. 3, 321-322.