Abstract
Glycan microarrays, carrying hundreds of different sugars on chip surfaces, have become a standard tool for the study of interactions of biomolecules with carbohydrates. The chip-based format offers important advantages, including the ability to screen in parallel several thousand binding events on a single slide, the minimal amount of sample required for one experiment, and the multivalent display of sugars on the chip that mimics the presentation of carbohydrates in nature. This chapter presents recent advances and future challenges in glycan microarray technology. We describe different immobilization and detection methods as well as applications in glycomics, drug discovery, and biomedicine.
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References
Laurent, N., Voglmeir, J., and Flitsch, S. L. (2008) Glycoarrays - tools for determining protein-carbohydrate interactions and glycoenzyme specificity. Chem. Commun., 4400–4412.
Horlacher, T., and Seeberger, P. H. (2008) Carbohydrate arrays as tools for research and diagnostics. Chem. Soc. Rev. 37, 1414–1422.
Park, S., Lee, M. R., and Shin, I. (2008) Carbohydrate microarrays as powerful tools in studies of carbohydrate-mediated biological processes. Chem. Commun., 4389–4399.
Wu, C. Y., Liang, P. H., and Wong, C. H. (2009) New development of glycan arrays. Org. Biomol. Chem. 7, 2247–2254.
de Paz, J. L., Horlacher, T., and Seeberger, P. H. (2006) Oligosaccharide microarrays to map interactions of carbohydrates in biological systems. Methods Enzymol. 415, 269–292.
de Paz, J. L., and Seeberger, P. H. (2006) Recent advances in carbohydrate microarrays. QSAR Comb. Sci. 25, 1027–1032.
Shin, I., Park, S., and Lee, M. R. (2005) Carbohydrate microarrays: An advanced technology for functional studies of glycans. Chem. Eur. J. 11, 2894–2901.
Adams, E. W., Ratner, D. M., Bokesch, H. R., McMahon, J. B., O’Keefe, B. R., and Seeberger, P. H. (2004) Oligosaccharide and glycoprotein microarrays as tools in HIV glycobiology: Glycan-dependent gp120/protein interactions. Chem. Biol. 11, 875–881.
Park, S., Lee, M. R., Pyo, S. J., and Shin, I. (2004) Carbohydrate chips for studying high-throughput carbohydrate-protein interactions. J. Am. Chem. Soc. 126, 4812–4819.
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.
Noti, C., de Paz, J. L., Polito, L., and Seeberger, P. H. (2006) Preparation and use of microarrays containing synthetic heparin oligosaccharides for the rapid analysis of heparin-protein interactions. Chem. Eur. J. 12, 8664–8686.
Calarese, D. A., Lee, H. K., Huang, C. Y., Best, M. D., Astronomo, R. D., Stanfield, R. L., Katinger, H., Burton, D. R., Wong, C. H., and Wilson, I. A. (2005) Dissection of the carbohydrate specificity of the broadly neutralizing-anti-HIV-1 antibody 2 G12. Proc. Natl. Acad. Sci. U.S.A. 102, 13372–13377.
Manimala, J. C., Li, Z., Jain, A., VedBrat, S., and Gildersleeve, J. C. (2005) Carbohydrate array analysis of anti-Tn antibodies and lectins reveals unexpected specificities: implications for diagnostic and vaccine development. ChemBioChem 6, 2229–2241.
Seeberger, P. H., and Werz, D. B. (2007) Synthesis and medical applications of oligosaccharides. Nature 446, 1046–1051.
Zhu, X. M., and Schmidt, R. R. (2009) New Principles for Glycoside-Bond Formation. Angew. Chem. Int. Ed. 48, 1900–1934.
Boltje, T. J., Buskas, T., and Boons, G. J. (2009) Opportunities and challenges in synthetic oligosaccharide and glycoconjugate research. Nature Chem. 1, 611–622.
Zhang, Z. Y., Ollmann, I. R., Ye, X. S., Wischnat, R., Baasov, T., and Wong, C. H. (1999) Programmable one-pot oligosaccharide synthesis. J. Am. Chem. Soc. 121, 734–753.
Plante, O. J., Palmacci, E. R., and Seeberger, P. H. (2001) Automated solid-phase synthesis of oligosaccharides. Science 291, 1523–1527.
Seeberger, P. H. (2008) Automated oligosaccharide synthesis. Chem. Soc. Rev. 37, 19–28.
Seeberger, P. H., and Werz, D. B. (2005) Automated synthesis of oligosaccharides as a basis for drug discovery. Nat. Rev. Drug Discov. 4, 751–763.
Werz, D. B., and Seeberger, P. H. (2005) Carbohydrates as the next frontier in pharmaceutical research. Chem. Eur. J. 11, 3194–3206.
Xia, B. Y., Kawar, Z. S., Ju, T. Z., Alvarez, R. A., Sachdev, G. P., and Cummings, R. D. (2005) Versatile fluorescent derivatization of glycans for glycomic analysis. Nat. Methods 2, 845–850.
Liu, Y., Feizi, T., Carnpanero-Rhodes, M. A., Childs, R. A., Zhang, Y. N., Muiioy, B., Evans, P. G., Osborn, H. M. I., Otto, D., Crocker, P. R., and Chai, W. C. (2007) Neoglycolipid probes prepared via oxime ligation for microarray analysis of oligosaccharide-protein interactions. Chem. Biol. 14, 847–859.
Brun, M. A., Disney, M. D., and Seeberger, P. H. (2006) Miniaturization of microwave-assisted carbohydrate functionalization to create oligosaccharide microarrays. ChemBioChem 7, 421–424.
Lee, M., and Shin, I. (2005) Facile preparation of carbohydrate microarrays by site-specific, covalent immobilization of unmodified carbohydrates on hydrazide-coated glass slides. Org. Lett. 7, 4269–4272.
Zhi, Z. L., Powell, A. K., and Turnbull, J. E. (2006) Fabrication of carbohydrate microarrays on gold surfaces: Direct attachment of nonderivatized oligosaccharides to hydrazide-modified self-assembled monolayers. Anal. Chem. 78, 4786–4793.
Wang, D. N., Liu, S. Y., Trummer, B. J., Deng, C., and Wang, A. L. (2002) Carbohydrate microarrays for the recognition of cross-reactive molecular markers of microbes and host cells. Nat. Biotechnol. 20, 275–281.
Shipp, E. L., and Hsieh-Wilson, L. C. (2007) Profiling the sulfation specificities of glycosaminoglycan interactions with growth factors and chemotactic proteins using microarrays. Chem. Biol. 14, 195–208.
Fukui, S., Feizi, T., Galustian, C., Lawson, A. M., and Chai, W. G. (2002) Oligosaccharide microarrays for high-throughput detection and specificity assignments of carbohydrate-protein interactions. Nat. Biotechnol. 20, 1011–1017.
Ko, K. S., Jaipuri, F. A., and Pohl, N. L. (2005) Fluorous-based carbohydrate microarrays. J. Am. Chem. Soc. 127, 13162–13163.
Alvarez, R. A., and Blixt, O. (2006) Identi-fication of ligand specificities for glycan-binding proteins using glycan arrays. Methods Enzymol. 415, 292–310.
Chevolot, Y., Bouillon, C., Vidal, S., Morvan, F., Meyer, A., Cloarec, J. P., Jochum, A., Praly, J. P., Vasseur, J. J., and Souteyrand, E. (2007) DNA-based carbohydrate biochips: a platform for surface glyco-engineering. Angew. Chem. Int. Ed. 46, 2398–2402.
Bryan, M. C., Fazio, F., Lee, H. K., Huang, C. Y., Chang, A., Best, M. D., Calarese, D. A., Blixt, C., Paulson, J. C., Burton, D., Wilson, I. A., and Wong, C. H. (2004) Covalent display of oligosaccharide arrays in microtiter plates. J. Am. Chem. Soc. 126, 8640–8641.
Lee, J. C., Wit, C. Y., Apon, J. V., Siuzdak, G., and Wong, C. H. (2006) Reactivity-based one-pot synthesis of the tumor-associated antigen N3 minor octasaccharide for the development of a photocleavable DIOS-MS sugar array. Angew. Chem. Int. Ed. 45, 2753–2757.
Song, E.-H., and Pohl, N. L. B. (2009) Carbohydrate arrays: recent developments in fabrication and detection methods with applications. Curr. Opin. Chem. Biol. 13, 626–632.
Ratner, D. M., Adams, E. W., Su, J., O’Keefe, B. R., Mrksich, M., and Seeberger, P. H. (2004) Probing protein-carbohydrate interactions with microarrays of synthetic oligosaccharides. ChemBioChem 5, 379–382.
Smith, E. A., Thomas, W. D., Kiessling, L. L., and Corn, R. M. (2003) Surface plasmon resonance imaging studies of protein-carbohydrate interactions. J. Am. Chem. Soc. 125, 6140–6148.
Karamanska, R., Clarke, J., Blixt, O., MacRae, J. I., Zhang, J. Q. Q., Crocker, P. R., Laurent, N., Wright, A., Flitsch, S. L., Russell, D. A., and Field, R. A. (2008) Surface plasmon resonance imaging for real-time, label-free analysis of protein interactions with carbohydrate microarrays. Glycoconj. J. 25, 69–74.
de Boer, A. R., Hokke, C. H., Deelder, A. M., and Wuhrer, M. (2008) Serum antibody screening by surface plasmon resonance using a natural glycan microarray. Glycoconj. J. 25, 75–84.
Su, J., and Mrksich, M. (2002) Using mass spectrometry to characterize self-assembled monolayers presenting peptides, proteins, and carbohydrates. Angew. Chem. Int. Ed. 41, 4715–4718.
Laurent, N., Voglmeir, J., Wright, A., Blackburn, J., Pham, N. T., Wong, S. C. C., Gaskell, S. J., and Flitsch, S. L. (2008) Enzymatic glycosylation of peptide arrays on gold surfaces. ChemBioChem 9, 883–887.
Zhi, Z. L., Laurent, N., Powel, A. K., Karamanska, R., Fais, M., Voglmeir, J., Wright, A., Blackburn, J. M., Crocker, P. R., Russell, D. A., Flitsch, S., Field, R. A., and Turnbull, J. E. (2008) A versatile gold surface approach for fabrication and interrogation of glycoarrays. ChemBioChem 9, 1568–1575.
Ban, L., and Mrksich, M. (2008) On-chip synthesis and label-free assays of oligosaccharide arrays. Angew. Chem. Int. Ed. 47, 3396–3399.
Disney, M. D., and Seeberger, P. H. (2004) Aminoglycoside microarrays to explore interactions of antibiotics with RNAs and proteins. Chem. Eur. J. 10, 3308–3314.
Nimrichter, L., Gargir, A., Gortler, M., Altstock, R. T., Shtevi, A., Weisshaus, O., Fire, E., Dotan, N., and Schnaar, R. L. (2004) Intact cell adhesion to glycan microarrays. Glycobiology 14, 197–203.
Disney, M. D., and Seeberger, P. H. (2004) The use of carbohydrate microarrays to study carbohydrate-cell interactions and to detect pathogens. Chem. Biol. 11, 1701–1707.
Liang, P. H., Wang, S. K., and Wong, C. H. (2007) Quantitative analysis of carbohydrate-protein interactions using glycan microarrays: Determination of surface and solution dissociation constants. J. Am. Chem. Soc. 129, 11177–11184.
Park, S., and Shin, I. (2007) Carbohydrate microarrays for assaying galactosyltransferase activity. Org. Lett. 9, 1675–1678.
de Paz, J. L., Noti, C., Bohm, F., Werner, S., and Seeberger, P. H. (2007) Potentiation of fibroblast growth factor activity by synthetic heparin oligosaccharide glycodendrimers. Chem. Biol. 14, 879–887.
Houseman, B. T., and Mrksich, M. (2002) Carbohydrate arrays for the evaluation of protein binding and enzymatic modification. Chem. Biol. 9, 443–454.
de Paz, J. L., Noti, C., and Seeberger, P. H. (2006) Microarrays of synthetic heparin oligosaccharides. J. Am. Chem. Soc. 128, 2766–2767.
de Paz, L. L., Moseman, E. A., Noti, C., Polito, L., von Andrian, U. H., and Seeberger, P. H. (2007) Profiting heparin-chemokine interactions using synthetic tools. ACS Chem. Biol. 2, 735–744.
de Paz, J. L., and Seeberger, P. H. (2008) Deciphering the glycosaminoglycan code with the help of microarrays. Mol. BioSyst. 4, 707–711.
Dube, D. H., and Bertozzi, C. R. (2005) Glycans in cancer and inflammation. Potential for therapeutics and diagnostics. Nat. Rev. Drug Discov. 4, 477–488.
Huang, C. Y., Thayer, D. A., Chang, A. Y., Best, M. D., Hoffmann, J., Head, S., and Wong, C. H. (2006) Carbohydrate microarray for profiling the antibodies interacting with Globo H tumor antigen. Proc. Natl. Acad. Sci. U.S.A. 103, 15–20.
Wang, C. C., Huang, Y. L., Ren, C. T., Lin, C. W., Hung, J. T., Yu, J. C., Yu, A. L., Wu, C. Y., and Wong, C. H. (2008) Glycan microarray of Globo H and related structures for quantitative analysis of breast cancer. Proc. Natl. Acad. Sci. U.S.A. 105, 11661–11666.
Blixt, O., Hoffmann, J., Svenson, S., and Norberg, T. (2008) Pathogen specific carbohydrate antigen microarrays: a chip for detection of Salmonella O-antigen specific antibodies. Glycoconj. J. 25, 27–36.
Kamena, F., Tamborrini, M., Liu, X. Y., Kwon, Y. U., Thompson, F., Pluschke, G., and Seeberger, P. H. (2008) Synthetic GPI array to study antitoxic malaria response. Nat. Chem. Biol. 4, 238–240.
Stevens, J., Blixt, O., Glaser, L., Taubenberger, J. K., Palese, P., Paulson, J. C., and Wilson, I. A. (2006) Glycan microarray analysis of the hemagglutinins from modern and pandemic influenza viruses reveals different receptor specificities. J. Mol. Biol. 355, 1143–1155.
Stevens, J., Blixt, O., Tumpey, T. M., Taubenberger, J. K., Paulson, J. C., and Wilson, I. A. (2006) Structure and receptor specificity of the hemagglutinin from an H5N1 influenza virus. Science 312, 404–410.
Childs, R. A., Palma, A. S., Wharton, S., Matrosovich, T., Liu, Y., Chai, W. G., Campanero-Rhodes, M. A., Zhang, Y. B., Eickmann, M., Kiso, M., Hay, A., Matrosovich, M., and Feizi, T. (2009) Receptor-binding specificity of pandemic influenza A (H1N1) 2009 virus determined by carbohydrate microarray. Nat. Biotechnol. 27, 797–799.
Acknowledgments
We thank the Spanish Research Council (CSIC) (Grant 200880I041), the Spanish Ministry of Science and Innovation (Grant CTQ2009-07168), Junta de Andalucía (Grant P07-FQM-02969, “Incentivo a Proyecto Internacional”), and the European Union (FEDER support and Marie Curie Reintegration Grant) for financial support. Generous financial support from the Max-Planck Society is gratefully acknowledged.
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de Paz, J.L., Seeberger, P.H. (2012). Recent Advances and Future Challenges in Glycan Microarray Technology. In: Chevolot, Y. (eds) Carbohydrate Microarrays. Methods in Molecular Biology, vol 808. Humana Press. https://doi.org/10.1007/978-1-61779-373-8_1
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DOI: https://doi.org/10.1007/978-1-61779-373-8_1
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