Chiral-auxiliary-mediated 1,2-cis-glycosylations for the solid-supported synthesis of a biologically important branched α-glucan

Nature Chemistry

Volumn 2, Issue 7, 2010, Pages 552-557

  Boltje, Thomas J ^a   Kim, Jin Hwan ^a   Park, Jin ^a   Boons, Geert Jan ^a  

^a UNIVERSITY OF GEORGIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GLUCAN; GLYCOSIDE;

ARTICLE; CHEMISTRY; GLYCOSYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS;

GLUCANS; GLYCOSIDES; GLYCOSYLATION; MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM;

EID: 77954007720     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.663     Document Type: Article

References (29)

1. Ohtsubo, K. & Marth, J. D. Glycosylation in cellular mechanisms of health and disease. Cell 126, 855-867 (2006).
2. Brockhausen, I. Mucin-type O-glycans in human colon and breast cancer: glycodynamics and functions. EMBO Rep. 7, 599-604 (2006).
3. Crocker, P. R., Paulson, J. C. & Varki, A. Siglecs and their roles in the immune system. Nature Rev. Immunol. 7, 255-266 (2007).
4. Van Kooyk, Y. & Rabinovich, G. A. Protein-glycan interactions in the control of innate and adaptive immune responses. Nature Immunol. 9, 593-601 (2008).
5. Raman, R. et al. Glycomics: an integrated systems approach to structure- function relationships of glycans. Nature Methods 2, 817-824 (2005).
6. Pilobello, K. T. & Mahal, L. K. Deciphering the glycocode: the complexity and analytical challenge of glycomics. Curr. Opin. Chem. Biol. 11, 300-305 (2007).
7. Timmer, M. S., Stocker, B. L. & Seeberger, P. H. Probing glycomics. Curr. Opin. Chem. Biol. 11, 59-65 (2007).
8. Laurent, N., Voglmeir, J. & Flitsch, S. L. Glycoarrays-tools for determining protein-carbohydrate interactions and glycoenzyme specificity. Chem. Commun. 4400-4412 (2008).
9. Codee, J. D. C. et al. Thioglycosides in sequential glycosylation strategies. Chem. Soc. Rev. 34, 769-782 (2005).
10. Buskas, T., Ingale, S. & Boons, G. J. Glycopeptides as versatile tools for glycobiology. Glycobiology 16, 113R-136R (2006).
11. Wang, Y. H., Ye, X. S. & Zhang, L. H. Oligosaccharide assembly by one-pot multi-step strategy. Org. Biomol. Chem. 5, 2189-2200 (2007).
12. Boltje, T. J., Buskas, T. & Boons, G. J. Opportunities and challenges in synthetic oligosaccharide and glycoconjugate research. Nature Chem. 1, 611-622 (2009).
13. Zhu, X. M. & Schmidt, R. R. New principles for glycoside-bond formation. Angew. Chem. Int. Ed. 48, 1900-1934 (2009).
14. Seeberger, P. H. Automated oligosaccharide synthesis. Chem. Soc. Rev. 37, 19-28 (2008).
15. Plante, O. J., Palmacci, E. R. & Seeberger, P. H. Automated solid-phase synthesis of oligosaccharides. Science 291, 1523 (2001).
16. Demchenko, A. V. Stereoselective chemical 1,2-cis O-glycosylation: from 'sugar ray' to modern techniques of the 21st century. Synlett 1225-1240 (2003).
17. Jonke, S., Liu, K. G. & Schmidt, R. R. Solid-phase oligosaccharide synthesis of a small library of N-glycans. Chem. Eur. J. 12, 1274-1290 (2006).
18. Werz, D. B., Castagner, B. & Seeberger, P. H. Automated synthesis of the tumorassociated carbohydrate antigens Gb-3 and Globo-H: incorporation of alphagalactosidic linkages. J. Am. Chem. Soc. 129, 2770-2771 (2007).
19. Codee, J. D., Krock, L., Castagner, B. & Seeberger, P. H. Automated solid-phase synthesis of protected oligosaccharides containing beta-mannosidic linkages. Eur. J. Chem. 14, 3987-3994 (2008).
20. Kim, J. H., Yang, H. & Boons, G. J. Stereoselective glycosylations using chiral auxiliaries. Angew. Chem. Int. Ed. 44, 947-949 (2005).
21. Kim, J. H., Yang, H., Park, J. & Boons, G. J. A general strategy for stereoselective glycosylations. J. Am. Chem. Soc. 127, 12090-12097 (2005).
22. Zhu, T. & Boons, G. J. A new set of orthogonal-protecting groups for oligosaccharide synthesis on a polymeric support. Tetrahedron: Asymmetry 11, 199-205 (2000).
23. Nicolaou, K. C., Winssinger, N., Pastor, J. & DeRoose, F. A general and highly efficient solid phase synthesis of oligosaccharides. Total synthesis of a heptasaccharide phytoalexin elicitor (HPE). J. Am. Chem. Soc. 119, 449-450 (1997).
24. Zhao, C., Li, M., Luo, Y. & Wu,W. Isolation and structural characterization of an immunostimulating polysaccharide from fuzi, Aconitum carmichaeli. Carbohydr. Res. 341, 485-491 (2006).
25. Bittencourt, V. C. et al. An alpha-glucan of Pseudallescheria boydii is involved in fungal phagocytosis and Toll-like receptor activation. J. Biol. Chem. 281, 22614-22623 (2006).
26. Van Bueren, A. L. et al. Identification and structural basis of binding to host lung glycogen by streptococcal virulence factors. Nature Struct. Mol. Biol. 14, 76-84 (2007).
27. Wu, X. & Schmidt, R. R. Solid-phase synthesis of complex oligosaccharides using a novel capping reagent. J. Org. Chem. 69, 1853-1857 (2004).
28. Wu, X., Grathwohl, M. & Schmidt, R. R. Efficient solid-phase synthesis of a complex, branched N-glycan hexasaccharide: use of a novel linker and temporary-protecting-group pattern. Angew. Chem. Int. Ed. 41, 4489-4493 (2002).
29. Wang, C. C. et al. Regioselective one-pot protection of carbohydrates. Nature 446, 896-899 (2007).