Facile preparation of fluorescent neoglycoproteins using p-nitrophenyl anthranilate as a heterobifunctional linker

Bioconjugate Chemistry

Volumn 20, Issue 8, 2009, Pages 1618-1624

  Luyai, Anthony ^a   Lasanajak, Yi ^a   Smith, David F ^a   Cummings, Richard D ^a   Song, Xuezheng ^a  

^a EMORY UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; ESTERS; FLUORESCENCE;

ANTHRANILATE; AROMATIC AMINES; CONDITION; FACILE PREPARATION; GLASS SLIDES; GLYCANS; HETEROBIFUNCTIONAL LINKER; NEOGLYCOCONJUGATES; REDUCTIVE AMINATION; UV ABSORPTION;

POLYSACCHARIDES;

ANTHRANILIC ACID 4 NITROPHENYL ESTER; ANTHRANILIC ACID DERIVATIVE; AROMATIC AMINE; GLYCAN; LECTIN; NEOGLYCOPROTEIN; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CONJUGATION; FLUORESCENCE; ULTRAVIOLET SPECTROSCOPY;

ANTHRANILIC ACIDS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FLUORESCENCE; GLYCOPROTEINS; MOLECULAR STRUCTURE; POLYSACCHARIDES;

EID: 70349147430     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc900189h     Document Type: Article

References (34)

1. Varki, A., Cummings, R. D., Esko, J. D., Freeze, H. H., Stanley, P., Bertozzi, C. R., Hart, G. W., Etzler, M. E. (2009) Essentials of Glycobiology, 2nd ed., Cold Spring Harbor Press, New York.
2. Wong, S. Y. C. (1995) Neoglycoconjugates and their applications in glycobiology. Curr. Opin. Struct. Biol. 5, 599-604.
3. Lee, R. T., and Lee, Y. C. (1997) Neoglycoconjugates. Glycosciences 55-77.
4. Bovin, N. V. (2003) Neoglycoconjugates as probes in glycobiology. NATO Sci. Seri., II 129, 207-225.
5. Davis, B. G. (2002) Synthesis of glycoproteins. Chem. Rev. 102, 579-602.
6. Pratt, M. R., and Bertozzi, C. R. (2005) Synthetic glycopeptides and glycoproteins as tools for biology. Chem. Soc. Rev. 34, 58-68.
7. Slovin, S. F., Keding, S. J., and Ragupathi, G. (2005) Carbohydrate vaccines as immunotherapy for cancer. Immunol. Cell. Biol. 83, 418-428
8. Ouerfelli, O., Warren, J. D., Wilson, R. M., and Danishefsky, S. J. (2005) Synthetic carbohydrate-based antitumor vaccines: challenges and opportunities. Expert Rev. Vaccines 4, 677-685 (Pubitemid 41530591)
9. Lloyd, K. O. (2000) Carbohydrate vaccines for the immunotherapy of cancer. Drug News Perspect. 13, 463-470
10. Ada, G., and Isaacs, D. (2003) Carbohydrate-protein conjugate vaccines. Clin. Microbiol. Infect. 9, 79-85.
11. Roy, R. (2004) New trends in carbohydrate-based vaccines. Drug Discovery Today: Technologies 1, 327-336.
12. Stowell, C. P., and Lee, V. C. (1980) Neoglycoproteins: the preparation and application of synthetic glycoproteins. Adv. Carbohydr. Chem. Biochem. 37, 225-281
13. Macmillan, D., and Bertozzi, C. R. (2000) New directions in glycoprotein engineering. Tetrahedron 56, 9515-9525.
14. Stowell, C. P., and Lee, Y. C. (1982) Preparation of neoglycoproteins using 2-imino-2-methoxyethyl 1-thioglycosides. Methods Enzymol. 83, 278-288
15. Stowell, C. P., and Lee, Y. C. (1980) Preparation of some new neoglycoproteins by amidination of bovine serum albumin using 2-imino-2-methoxyethyl 1-thioglycosides. Biochemistry 19, 4899-4904
16. Mawas, F., Niggemann, J., Jones, C., Corbel, M. J., Kamerling, J. P., and Vliegenthart, J. F. (2002) Immunogenicity in a mouse model of a conjugate vaccine made with a synthetic single repeating unit of type 14 pneumococcal polysaccharide coupled to CRM197. Infect. Immun. 70, 5107-5114 (Pubitemid 34907324)
17. Wang, Q., Chan, T. R., Hilgraf, R., Fokin, V. V., Sharpless, K. B., and Finn, M. G. (2003) Bioconjugation by copper(I)-catalyzed azide-alkyne [3 + 2] cycloaddition. J. Am. Chem. Soc. 125, 3192-3193
18. Crich, D., and Yang, F. (2008) Synthesis of neoglycoconjugates by the desulfurative rearrangement of allylic disulfides. J. Org. Chem. 73, 7017-7027.
19. Kubler-Kielb, J., and Pozsgay, V. (2005) A new method for conjugation of carbohydrates to proteins using an aminooxythiol heterobifunctional linker. J. Org. Chem. 70, 6987-6990 (Pubitemid 41134407)
20. Wong, S. Y., Guile, G. R., Dwek, R. A., and Arsequell, G. (1994) Synthetic glycosylation of proteins using N-(betasaccharide) iodoacetamides: applications in site-specific glycosylation and solid-phase enzymic oligosaccharide synthesis. Biochem. J. 300 (Pt 3), 843-850
21. Shao, M. C., Chen, L. M., and Wold, F. (1990) Complex neoglycoproteins. Methods Enzymol. 184, 653-659
22. Wu, X., Ling, C. C., and Bundle, D. R. (2004) A new homobifunctional p-nitro phenyl ester coupling reagent for the preparation of neoglycoproteins. Org. Lett. 6, 4407-4410 (Pubitemid 39611775)
23. Gildersleeve, J. C., Oyelaran, O., Simpson, J. T., and Allred, B. (2008) Improved procedure for direct coupling of carbohydrates to proteins via reductive amination. Bioconjugate Chem. 19, 1485-1490 (Pubitemid 352032350)
24. Mencke, A. J., Cheung, D. T., and Wold, F. (1987) Attachment of oligosaccharide-asparagine derivatives to proteins: activation of asparagine with ninhydrin and coupling to protein by reductive amination. Methods Enzymol. 138, 409-413
25. Song, X., Xia, B., Lasanajak, Y., Smith, D. F., and Cummings, R. D. (2008) Quantifiable fluorescent glycan microarrays. Glycoconjugate J. 25, 15-25.
26. Ueda, K., Katagiri, T., Shimada, T., Irie, S., Sato, T. A., Nakamura, Y., and Daigo, Y. (2007) Comparative profiling of serum glycoproteome by sequential purification of glycoproteins and 2-nitrobenzensulfenyl (NBS) stable isotope labeling: a new approach for the novel biomarker discovery for cancer. J. Proteome Res. 6, 3475-3483 (Pubitemid 47522738)
27. Yamashita, K., Kochibe, N., Ohkura, T., Ueda, I., and Kobata, A. (1985) Fractionation of L-fucose-containing oligosaccharides on immobilized Aleuria aurantia lectin. J. Biol. Chem. 260, 4688-4693 (Pubitemid 15034604)
28. Green, E. D., Brodbeck, R. M., and Baenziger, J. U. (1987) Lectin affinity high-performance liquid chromatography. Interactions of N-glycanase-released oligosaccharides with Ricinus communis agglutinin I and Ricinus communis agglutinin II. J. Biol. Chem. 262, 12030-12039
29. Shibuya, N., Goldstein, I. J., Broekaert, W. F., Nsimba-Lubaki, M., Peeters, B., and Peumans, W. J. (1987) The elderberry (Sambucus nigra L.) bark lectin recognizes the Neu5Ac(alpha 2-6)Gal/GalNAc sequence. J. Biol. Chem. 262, 1596-1601
30. Munoz, F. J., Perez, J., Rumbero, A., Santos, J. I., Canada, F. J., Andre, S., Gabius, H. J., Jimenez-Barbero, J., Sinisterra, J. V., Hernaiz, M. J. (2009) Glycan tagging to produce bioactive ligands for a surface plasmon resonance (SPR) study via immobilization on different surfaces, Bioconjugate Chem. 20, 673-682.
31. Song, X., Xia, B., Lasanajak, Y., Stowell, S. R., Smith, D. F., Cummings, R. D. (2009) Novel fluorescent glycan microarray strategy reveals ligands for galectins. Chem. Biol. 16, 36-47.
32. Nyame, A. K., Kawar, Z. S., and Cummings, R. D. (2004) Antigenic glycans in parasitic infections: implications for vaccines and diagnostics. Arch. Biochem. Biophys. 426, 182-200.
33. Blixt, O., Head, S., Mondala, T., Scanlan, C., Huflejt, M. E., Alvarez, R., Bryan, M. C., Fazio, F., Calarese, D., Stevens, J., Razi, N., Stevens, D. J., Skehel, J. J., van Die, I., Burton, D. R., Wilson, I. A., Cummings, R., Bovin, N., Wong, C. H., and Paulson, J. C. (2004) Printed covalent glycan array for ligand profiling of diverse glycan binding proteins. Proc. Natl. Acad. Sci. U.S.A. 101, 17033-17038 (Pubitemid 39627769)
34. de Boer, A. R., Hokke, C. H., Deelder, A. M., and Wuhrer, M. (2007) General microarray technique for immobilization and screening of natural glycans. Anal. Chem. 79, 8107-8113