Synthesis and medical applications of oligosaccharides

Nature

Volumn 446, Issue 7139, 2007, Pages 1046-1051

  Seeberger, Peter H ^a   Werz, Daniel B ^a,b  

^a ETH ZURICH   (Switzerland)

^b UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACARBOSE; ANTHRAX VACCINE; BACTERIAL VACCINE; CANCER ANTIBODY; CANCER VACCINE; CARBOHYDRATE; FONDAPARINUX; GLYCAN; GLYCOCONJUGATE; GLYCOSPHINGOLIPID; HAEMOPHILUS INFLUENZAE TYPE B VACCINE; HEPARIN; LIPOPHOSPHOGLYCAN; LOW MOLECULAR WEIGHT HEPARIN; MONOSACCHARIDE; NEISSERIA MENINGITIDIS VACCINE; OLIGOSACCHARIDE; OSELTAMIVIR; PNEUMOCOCCUS VACCINE; POLYMER; QUANTUM DOT; TYPHOID VACCINE; UNCLASSIFIED DRUG;

CARBOHYDRATE; DRUG DEVELOPMENT; GENOMICS; PROTEIN; PROTEOMICS; RESEARCH WORK; VACCINE;

ANTICOAGULATION; BACILLUS ANTHRACIS; BACTERIAL MEMBRANE; BIOENGINEERING; CARBOHYDRATE ANALYSIS; CARBOHYDRATE SYNTHESIS; DRUG HALF LIFE; FLUORESCENCE ANALYSIS; GLYCOBIOLOGY; HAEMOPHILUS INFLUENZAE TYPE B; HUMAN; LEISHMANIASIS; MALARIA; NEISSERIA MENINGITIDIS; NONHUMAN; ONE POT SYNTHESIS; POLYMERASE CHAIN REACTION; PRIORITY JOURNAL; REVIEW; SALMONELLA TYPHI; STREPTOCOCCUS PNEUMONIAE; SURFACE PLASMON RESONANCE;

EID: 34247556420     PISSN: 00280836     EISSN: 14764687     Source Type: Journal    
DOI: 10.1038/nature05819     Document Type: Review

References (93)

1. Insight: Human genomics and medicine. Nature 429, 439-481 (2004).
2. Insight: Proteomics. Nature 422, 191-237 (2003).
3. Varki, A. et al. Essentials of Glycobiology (Cold Spring Harbor Laboratory Press, 1999).
4. Hunkapiller, T., Kaiser, R. J., Koop, B. F. & Hood, L. Large-scale and automated DNA sequence determination. Science 354, 59-67 (1991).
5. Grant, G. A., Crankshaw, M. W. & Gorka, J. Edman sequencing as tool for characterization of synthetic peptides. Methods Enzymol. 289, 395-419 (1997).
6. Caruthers, M. H. Gene synthesis machines: DNA chemistry and its uses. Science 230, 281-285 (1985).
7. Merrifield, B. Concept and early development of solid-phase peptide synthesis. Methods Enzymol. 289, 3-13 (1997).
8. Ernst, B., Hart, G. W. & Sinaÿ, P. Carbohydrates in Chemistry and Biology Pt 1 Chemistry of Saccharides (Wiley-VCH, Weinheim, 2000).
9. Mayer, T. G., Kratzer, B. & Schmidt, R. R. Synthesis of a GPI anchor of the yeast Saccharomyces cerevisiae. Angew. Chem. Int. Ed. Engl. 33, 2177-2181 (1994).
10. Seifert, J., Lergenmuller, M. & Ito, Y. Synthesis of an α-(2,3)-sialylated complex-type undecasaccharide. Angew. Chem. Int. Ed. 39, 531-534 (2000).
11. Wang, Z.-G. et al. Toward fully synthetic homogeneous glycoproteins: a high mannose core containing glycopeptide containing carrying full H-type 2 human blood group specifity. Angew. Chem. Int. Ed. 40, 1728-1732 (2001).
12. Ashline, D., Singh, S., Hanneman, A. & Reinhold, V. Congruent strategies for carbohydrate sequencing. 1. Mining structural details by MSn. Anal. Chem. 77, 6250-6262 (2005).
13. Laroy, W., Contreras, R. & Callewaert, N. Glycome mapping on DNA sequencing equipment. Nature Protocols 1, 397-405 (2006).
14. Dell, A. & Morris, H. R. Glycoprotein structure determination by mass spectrometry. Science 291, 2351-2356 (2001).
15. Venkataraman, G., Shriver, Z., Raman, R. & Sasisekharan, R. Sequencing complex polysaccharides. Science 286, 537-542 (1999).
16. Chi, L. et al. Preparation and structural determination of large oligosaccharides derived from acharan sulfate. Carbohydr. Res. 341, 864-869 (2006).
17. Saad, O. M. & Leary, J. A. Heparin sequencing using enzymatic digestion and ESI-MSn with HOST: a heparin/HS oligosaccharide sequencing tool. Anal. Chem. 77, 5902-5911 (2005).
18. Nishimura, S. et al. High-throughput protein glycomics: combined use of chemoselective glycoblotting and MALDI-TOF/TOF mass spectrometry. Angew. Chem. Int. Ed. 44, 91-96 (2004).
19. Sears, P. & Wong, C.-H. Toward automated synthesis of oligosaccharides and glycoproteins. Science 291, 2344-2350 (2001).
20. Zhang, Z. et al. Programmable one-pot oligosaccharide synthesis. J. Am. Chem. Soc. 121, 734-753 (1999).
21. Nishimura, S. Automated glycosynthesizer 'Golgi' by mimicking biosynthetic process. Tanpakushitsu Kakusan Koso 48, 1220-1225 (2003).
22. Koeller, K. M. & Wong, C.-H. Enzymes for chemical synthesis. Nature 409, 232-234 (2001).
23. Wong, C.-H., Halcomb, R. L., Ichikawa, Y. & Kajimoto, T. Enzymes in organic synthesis: application to the problems of carbohydrate recognition. Angew. Chem. Int. Ed. Engl. 34, 412-432 (1995).
24. Gerngross, T. U. Advances in the production of human therapeutic proteins in yeasts and filamentous fungi. Nature Biotechnol. 22, 1409-1414 (2004).
25. Li, H. et al. Optimization of humanized IgGs in glycoengineered Pichia pastoris. Nature Biotechnol. 24, 210-215 (2006).
26. Plante, O. J., Palmacci, E. R. & Seeberger, P. H. Automated solid-phase synthesis of oligosaccharides. Science 291, 1523-1527 (2001).
27. Andrade, R. B., Plante, O. J., Melean, L. G. & Seeberger, P. H. Solid-phase oligosaccharide synthesis: preparation of complex structures using a novel linker and different glycosylating agents. Org. Lett. 1, 1811-1814 (1999).
28. Love, K. R. & Seeberger, P. H. Automated solid-phase synthesis of protected tumor-associated antigen and blood group determinant oligosaccharides. Angew. Chem. Int. Ed. 43, 602-605 (2004).
29. Werz, D. B., Castagner, B. & Seeberger, P. H. Automated synthesis of the tumor-associated carbohydrate antigens Gb-3 and Globo-H: incorporation of α-galactosidic linkages. J. Am. Chem. Soc. 129, 2770-2771 (2007).
30. Lockhart, D. J. & Winzeleer, E. A. Genomics, gene expression and DNA arrays. Nature 405, 827-836 (2000).
31. Zhu, H. et al. Global analysis of protein activities using proteome chips. Science 293, 2101-2105 (2001).
32. Wang, D. et al. Carbohydrate microarrays for the recognition of cross-reactive molecular markers of microbes and host cells. Nature Biotechnol. 20, 275-281 (2002).
33. Fukui, S. et al. Oligosaccharide microarrays for high-throughput detection and specificity assignments of carbohydrate-protein interactions. Nature Biotechnol. 20, 1011-1017 (2002).
34. Park, S. & Shin, I. Fabrication of carbohydrate chips for studying protein-carbohydrate interactions. Angew. Chem. Int. Ed. 41, 3180-3182 (2002).
35. Fazio, F. et al. Synthesis of sugar arrays in microtiter plate. J. Am. Chem. Soc. 124, 14397-14402 (2002).
36. Houseman, B. T. & Mrksich, M. Carbohydrate arrays for the evaluation of protein binding and enzymatic modification. Chem. Biol. 9, 443-454 (2002).
37. Adams, E. W. et al. Encoded fiber optic microsphere arrays for probing protein-carbohydrate interactions. Angew. Chem. Int. Ed. 42, 5317-5320 (2003).
38. Culf, A. S., Cuperlovic-Culf, M. & Ouellette, R. J. Carbohydrate microarrays: survey of fabrication techniques. OMICS 10, 289-310 (2006).
39. Ratner, D. M. et al. Probing protein-carbohydrate interactions with microarrays of synthetic oligosaccharides. ChemBioChem 5, 379-383 (2004).
40. Blixt, O. et al. Printed covalent glycan array for ligand profiling of diverse glycan binding proteins. Proc. Natl Acad. Sci. USA 101, 17033-17038 (2004).
41. Adams, E. W. et al. Oligosaccharide and glycoprotein microarrays as tools in HIV-glycobiology: glycan dependent gp120/protein interactions. Chem. Biol. 11, 875-881 (2004).
42. Scanlan, C. N. et al. The carbohydrate epitope of neutralizing anti HIV-1 antibody 2G12. Adv. Exp. Med. Biol. 535, 205-218 (2003).
43. Rudd, P. M., Wormald, M. R. & Dwek, R. A. Sugar-mediated ligand receptor interactions in the immune system. Trends Biotechnol. 22, 524-530 (2004).
44. Paulson J. C., Blixt, O. & Collins, B. E. Sweet spots in functional glycomics. Nature Chem. Biol. 2, 238-248 (2006).
45. Disney, M. D. & Seeberger, P. H. Aminoglycoside microarrays to explore carbohydrate-RNA interactions. Chem. Eur. J. 10, 3308-3314 (2004).
46. Disney, M. D., Magnet, S., Blanchard, J. S. & Seeberger, P. H. Aminoglycoside microarrays to study antibiotic resistance. Angew. Chem. Int. Ed. 43, 1591-1594 (2004).
47. Disney, M. D. & Seeberger, P. H. The use of carbohydrate microarrays to study carbohydrate-cell interactions and to detect pathogens. Chem. Biol. 11, 1701-1707 (2004).
48. Nimrichter, L. et al. Intact cell adhesion to glycan microarrays. Glycobiology 14,197-203 (2004).
49. Stevens, J. et al. Structure and receptor specificity of the hemagglutinin from an H5N1 influenza virus. Science 312, 404-410 (2006).
50. de Paz, J. L., Noti, C. & Seeberger, P. H. Microarrays of synthetic heparin oligosaccharides. J. Am. Chem. Soc. 128, 2766-2767 (2006).
51. de Paz, J. L., Spilmann, D. & Seeberger, P. H. Microarrays of heparin oligosaccharides obtained by nitrous acid depolymerization of heparin. Chem. Commun. 3116-3117 (2006).
52. Noti, C., de Paz, J. L. & Seeberger, P. H. Preparation and use of microarrays containing synthetic heparin oligosaccharides for the rapid analysis of heparin-protein interactions. Chem. Eur. J. 12, 8664-8686 (2006).
53. Tully, S. E., Rawat, M. & Hsieh-Wilson, L. C. Discovery of a TNF-α antagonist using chondroitin sulfate microarrays. J. Am. Chem. Soc. 128, 7740-7741 (2006).
54. Gama, C. I. et al. Sulfation patterns of glycosaminoglycans encode molecular recognition and activity. Nature Chem. Biol. 2, 467-473 (2006).
55. Schofield, L. et al. Synthetic GPI as a candidate anti-toxic vaccine in a model of malaria. Nature 418, 785-789 (2002).
56. Dotan, I. et al. Antibodies against laminaribioside and chitobioside are novel serologic markers in Crohn's disease. Gastroenterology 131, 366-378 (2006).
57. Huang, C. Y. et al. Carbohydrate microarray for profiling the antibodies interacting with Globo H tumor antigen. Proc. Natl Acad. Sci. USA 103, 15-20 (2006).
58. Pilobello, K. T., Krishnamoorthy, L., Slawek, D. & Mahal, L. K. Development of a lectin microarray for the rapid analysis of protein glycopatterns. ChemBioChem 6, 985-989 (2005).
59. Hsu, K. L., Pilobello, K. T. & Mahal, L. K. Analyzing the dynamic bacterial glycome with a lectin microarray approach. Nature Chem. Biol. 2, 153-157 (2006).
60. De Clercq, E. Antiviral agents against influenza A viruses. Nature Rev. Drug Discov. 5, 1015-1025 (2006).
61. Farina, V. & Brown, J. D. Tamiflu: the supply problem. Angew. Chem. Int. Ed. 45, 7330-7334 (2006).
62. Weizman, H. & Thor, Y. in Carbohydrate-Based Drug Discovery (ed. Wong, C.-H.) 661-684 (Wiley-VCH, Weinheim, 2003).
63. Capila, I. & Linhardt, R. J. Heparin-protein interactions. Angew. Chem. Int. Ed. 41, 390-412 (2002).
64. Petitou, M., Casu, B. & Lindahl, U. 1976-1983, a critical period in the history of heparin: the discovery of the antithrombin binding site. Biochimie 85, 83-89 (2003).
65. Petitou, M. & van Boeckel, C. A. A. A synthetic antithrombin binding pentasaccharide is now a drug! What comes next? Angew. Chem. Int. Ed. 43, 3118-3133 (2004).
66. Giangrande, P. L. F. Fondaparinux (Arixtra): a new anticoagulant. Int. J. Clin. Pract. 56, 615-617 (2002).
67. Noti, C. & Seeberger, P. H. Chemical approaches to define structure-activity relationships of heparin-like glycosaminoglycans. Chem. Biol. 12, 731-756 (2005).
68. Codée, J. D. C. et al. A modular strategy toward the synthesis of heparin-like oligosaccharides using monomeric building blocks in a sequential glycosylation strategy. J. Am. Chem. Soc. 127, 3767-3773 (2005).
69. de Paz, J.-L. et al. The activation of fibroblast growth factors by heparin: synthesis, structure, and biological activity of heparin-like oligosaccharides. ChemBioChem 2, 673-685 (2001).
70. Lee, J.-C. et al. Synthesis of heparin oligosaccharides. J. Am. Chem. Soc. 126, 476-477 (2004).
71. Truscheit, E. et al. Chemistry and biochemistry of microbial α-glucosidase inhibitors. Angew. Chem. Int. Ed. Engl. 20, 744-761 (1981).
72. Hakomori, S. Tumor-associated carbohydrate antigens defining tumor malignancy: basis for development of anti-cancer vaccines. Adv. Exp. Med. Biol. 491, 369-402 (2001).
73. Goldblatt, D. Recent developments in bacterial conjugate vaccines. J. Med. Microbiol. 47, 563-567 (1998).
74. Danishefsky, S. J. & Allen, J. R. From the laboratory to the clinic: a retrospective on fully synthetic carbohydrate based anticancer vaccines. Angew. Chem. Int. Ed. 39, 836-863 (2000).
75. Zhang, S. et al. Selection of tumor antigens as targets for immune attack using immunohistochemistry: I. Focus on gangliosides. Int. J. Cancer 3, 42-49 (1997).
76. Slovin, S. F., Keding, S. J. & Ragupathi, G. Carbohydrate vaccines as immunotherapy for cancer. Immunol. Cell Biol. 83, 418-428 (2005).
77. Ada, G. & Isaacs, D. Carbohydrate-protein conjugate vaccines. Clin. Microbiol. Infect. 9, 79-85 (2003).
78. Verez-Bencomo, V. et al. A synthetic conjugate polysaccharide vaccine against Haemophilus influenzae type b. Science 305, 522-525 (2004).
79. Daubenspeck, J. M. et al. Novel oligosaccharide side chains of the collagen-like region of BclA, the major glycoprotein of the Bacillus anthracis exosporium. J. Biol. Chem. 279, 30945-30953 (2004).
80. Werz, D. B. & Seeberger, P. H. Total synthesis of antigen Bacillus anthracis tetrasaccharide - creation of an anthrax vaccine candidate. Angew. Chem. Int. Ed. 44, 6315-6318 (2005).
81. Adamo, R., Saksena, R. & Kováč, P. Synthesis of the β-anomer of the spacer-equipped tetrasaccharide side chain of the major glycoprotein of the Bacillus anthracis exosporium. Carbohydr. Res. 340, 2579-2582 (2005).
82. Tamborrini, M. et al. Anti-carbohydrate antibodies for the detection of anthrax spores. Angew. Chem. Int. Ed. 45, 6581-6582 (2006).
83. Berhe, S., Schofield, L., Schwarz, R. T. & Gerold, P. Conservation of structure among glycosylphosphatidylinositol toxins from different geographic isolates of Plasmodium falciparum. Mol. Biochem. Parasitol. 103, 273-278 (1999).
84. Turco, S. J. & Descoteaux, A. The lipophosphoglycan of Leishmania parasites. Annu. Rev. Microbiol. 46, 65-94 (1992).
85. Hewitt, M. C. & Seeberger, P. H. Automated solid-phase synthesis of a branched Leishmania cap tetrasaccharide. Org. Lett. 3, 3699-3702 (2001).
86. Liu, X. et al. Enhancement of the immunogenicity of synthetic carbohydrates by conjugation to virosomes - a leishmaniasis vaccine candidate. ACS Chem. Biol. 1, 161-164 (2006).
87. Houseman, B. T., Gawalt, E. S. & Mrksich, M. Maleimide-functionalized self-assembled monolayers for the preparation of peptide and carbohydrate biochips. Langmuir 19, 1522-1531 (2003).
88. de la Fuente, J. M. et al. Gold glyconanoparticles as water-soluble polyvalent models to study carbohydrate interactions. Angew. Chem. Int. Ed. 40, 2258-2261 (2001).
89. Ratner, D. M., Adams, E. W., Disney, M. D. & Seeberger, P. H. Tools for glycomics: mapping interactions of carbohydrates in biological systems. ChemBioChem 5, 1375-1383 (2004).
90. Rye, P. D. Sweet and sticky: carbohydrate-coated magnetic beads. Nature Biotechnol. 14, 155-157 (1996).
91. Sun, X. L., Cui, W., Haller, C. & Chaikof, E. L. Site-specific multivalent carbohydrate labeling of quantum dots and magnetic beads. ChemBioChem 5, 1593-1596 (2004).
92. Ballell, L. et al. A new chemical probe for proteomics of carbohydrate-binding proteins. ChemBioChem 6, 291-295 (2005).
93. Disney, M. D., Zheng, J., Swager, T. M. & Seeberger, P. H. J. Am. Chem. Soc. 126, 13343-13346 (2004).