Bioconjugation using mutant glycosyltransferases for the site-specific labeling of biomolecules with sugars carrying chemical handles

Methods in Molecular Biology

Volumn 751, Issue , 2011, Pages 281-296

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

^a NATIONAL CANCER INSTITUTE   (United States)

Author keywords

2 Acetonyl 2 deoxy galactose (C2 keto Gal); Asn linked glycan (N glycan); Glycosyltransferase; Human polypeptidyl N acetylgalactosaminyltransferase (h pp Gal NAc T); Monoclonal antibody (mAb); Single chain antibody (scFv); 1,3 Galactosyltransferase ( 3Gal T)

Indexed keywords

ALPHA 1,3 GALACTOSYLTRANSFERASE; ASIALOFETUIN; BEVACIZUMAB; GLYCAN; GLYCOSYLTRANSFERASE; INFLIXIMAB; POLYPEPTIDYL ALPHA N ACETYLGALACTOSAMINYLTRANSFERASE; RITUXIMAB; TRASTUZUMAB; UNCLASSIFIED DRUG; ALPHA FETOPROTEIN; ASIALOGLYCOPROTEIN; DRUG CARRIER; EPIDERMAL GROWTH FACTOR RECEPTOR 2; GLYCOPEPTIDASE; GLYCOPROTEIN; HYBRID PROTEIN; OLIGOSACCHARIDE; SINGLE CHAIN FRAGMENT VARIABLE ANTIBODY; STAPHYLOCOCCUS PROTEIN A;

AFFINITY CHROMATOGRAPHY; ANTIBODY LABELING; BIOTINYLATION; CHEMOLUMINESCENCE; CONJUGATION; DEGALACTOSYLATION; DRUG DELIVERY SYSTEM; ENZYME ACTIVE SITE; ENZYME ENGINEERING; ENZYME SPECIFICITY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; NONHUMAN; POLYACRYLAMIDE GEL ELECTROPHORESIS; PROTEIN GLYCOSYLATION; PROTEIN MODIFICATION; SITE DIRECTED MUTAGENESIS; WESTERN BLOTTING; ARTICLE; BINDING SITE; CARBOHYDRATE METABOLISM; CHEMISTRY; GENETICS; GLYCOSYLATION; HUMAN; IMMUNOLOGY; MASS SPECTROMETRY; METABOLISM; METHODOLOGY; MUTATION; PROTEIN ENGINEERING; STAINING;

ALPHA-FETOPROTEINS; ASIALOGLYCOPROTEINS; BINDING SITES; BIOTINYLATION; CARBOHYDRATE METABOLISM; CHEMILUMINESCENT MEASUREMENTS; CHROMATOGRAPHY, AFFINITY; DRUG CARRIERS; GLYCOPROTEINS; GLYCOSYLATION; GLYCOSYLTRANSFERASES; HUMANS; MASS SPECTROMETRY; MUTATION; OLIGOSACCHARIDES; PEPTIDE-N4-(N-ACETYL-BETA-GLUCOSAMINYL) ASPARAGINE AMIDASE; PROTEIN ENGINEERING; RECEPTOR, ERBB-2; RECOMBINANT FUSION PROTEINS; SINGLE-CHAIN ANTIBODIES; STAINING AND LABELING; STAPHYLOCOCCAL PROTEIN A; SUBSTRATE SPECIFICITY;

EID: 80053340272     PISSN: 10643745     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-1-61779-151-2_17     Document Type: Chapter

References (14)

1. 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.
2. 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.
3. Pasek, M., Ramakrishnan, B., Boeggeman, E., Manzoni, M., Waybright, T. J., and Qasba, P. K. (2009) Bioconjugation and detection of lactosamine moiety using alpha1,3-galactosyltransferase mutants that transfer C2-modified galactose with a chemical handle. Bioconjug. Chem. 20, 608-618.
4. Carter, P. J. and Senter, P. D. (2008) Antibodydrug conjugates for cancer therapy. Cancer J. 14, 154-169.
5. 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.
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. 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. Bioconjug. Chem. 18, 806-814.
8. Ramakrishnan, B., Boeggeman, E. and Qasba, P. K. (2007) Novel method for in vitro O-glycosylation of proteins: application for bioconjugation. Bioconjug. Chem. 18, 1912-1918.
9. Boeggeman, E., Ramakrishnan, B., Pasek, M., Manzoni, M., Puri, A., Loomis, K. H., Waybright, T. J. and Qasba, P. K. (2009) Sitespecific conjugation of fluoroprobes to the remodeled Fc N-glycans of monoclonal antibodies using mutant glycosyltransferases: application for cell surface antigen detection. Bioconjug. Chem. 20, 1228-1236.
10. Ramakrishnan, B., Boeggeman, E., Manzoni, M., Zhu, Z., Loomis, K., Puri, A., Dimitrov, D. S. and Qasba P. K. (2009) Multiple site-specific in vitro labeling of single-chain antibody. Bioconjug. Chem. 20, 1383-1389.
11. 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.
12. Holland, M., Yagi, H., Takahashi, N., Kato, K., Savage, C. O., Goodall, D. M. and Jefferis, R. (2006) Differential glycosylation of polyclonal IgG, IgG-Fc and IgG-Fab isolated from the sera of patients with ANCA-associated systemic vasculitis. Biochim. Biophys. Acta. 1760, 669-677.
13. Dube, D. H., Prescher, J. A., Quang, C. N. and Bertozzi, C. R. (2006) Probing mucintype O-linked glycosylation in living animals. Proc. Natl. Acad. Sci. U S A. 103, 4819-4824.
14. Boeggeman, E., Ramakrishnan, B. and Qasba, P. K. (2003) The N-terminal stem region of bovine and human b1,4-galactosyltransferase I increases the in vitro folding efficiency of their catalytic domain from inclusion bodies. Prot. Expres. Purif. 30, 219-220.