Synthesis of pentaantennary N-glycans with bisecting GlcNac and core fucose

Angewandte Chemie - International Edition

Volumn 46, Issue 22, 2007, Pages 4173-4175

  Eller, Steffen ^a   Schuberth, Ralf ^a   Gundel, Gislinde ^a   Seifert, Joachim ^a   Unverzagt, Carlo ^a  

^a UNIVERSITY OF BAYREUTH   (Germany)

Author keywords

Carbohydrates; Glycoproteins; Glycosylation; Protecting groups; Steric hindrance

Indexed keywords

GLYCOPROTEINS; GLYCOSYLATION; OPTIMIZATION; SYNTHESIS (CHEMICAL);

BUILDING BLOCKS; PROTECTING GROUPS; STERIC HINDRANCE;

OLIGOSACCHARIDES;

FUCOSE; GLYCOPROTEIN; N ACETYLGLUCOSAMINYLTRANSFERASE; POLYSACCHARIDE;

ARTICLE; CARBOHYDRATE ANALYSIS; CHEMICAL MODEL; CHEMISTRY; CONFORMATION; GLYCOSYLATION; MOLECULAR GENETICS; SYNTHESIS;

CARBOHYDRATE CONFORMATION; CARBOHYDRATE SEQUENCE; FUCOSE; GLYCOPROTEINS; GLYCOSYLATION; MODELS, CHEMICAL; MOLECULAR SEQUENCE DATA; N-ACETYLGLUCOSAMINYLTRANSFERASES; POLYSACCHARIDES;

EID: 34250757684     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200604788     Document Type: Article

References (25)

1. B. Lowe, A. Varki, Essentials in Glycobiology, Cold Spring Harbor Laboratory Press, Cold Spring Harbor, 1999.
2. A. Düffels, S. V. Ley, J. Chem. Soc. Perkin Trans. 1 1999, 375.
3. D. M. Ratner, E. R. Swanson, P. H. Seeberger, Org. Lett. 2003, 5, 4717.
4. H. Weiss, C. Unverzagt, Angew. Chem. 2003, 115, 4389;
5. Angew. Chem. Int. Ed. 2003, 42, 4261.
6. G. M. Watt, G. J. Boons, Carbohydr. Res. 2004, 339, 181.
7. V. Y. Dudkin, J. S. Miller, S. J. Danishefsky, J. Am. Chem. Soc. 2004, 126, 736.
8. Y. Ito, S. Hagihara, I. Matsuo, K. Totani, Curr. Opin. Struct. Biol. 2005, 15, 481.
9. B. Li, H. Song, S. Hauser, L.-X. Wang, Org. Lett. 2006, 8, 3081.
10. T. W. Rising, T. D. Claridge, N. Davies, D. P. Gamblin, J. W. Moir, A. J. Fairbanks, Carbohydr. Res. 2006, 341, 1574.
11. S. Jonke, K. G. Liu, R. R. Schmidt, Chem. Eur. J. 2006, 12, 1274.
12. K. G. Rice, Anal. Biochem. 2000, 283, 10.
13. C. Unverzagt, Angew. Chem. 1997, 109, 2078;
14. Angew. Chem. Int. Ed. Engl. 1997, 36, 1989.
15. C. Unverzagt, J. Seifert, Tetrahedron Lett. 2000, 41, 4549.
16. R. Schuberth, C. Unverzagt, Tetrahedron Lett. 2005, 46, 4201.
17. J. Seifert, C. Unverzagt, Tetrahedron Lett. 1996, 37, 6527.
18. K. Yamashita, J. P. Kamerling, A. Kobata, J. Biol. Chem. 1982, 257, 12 809.
19. T. Taguchi, K. Kitajima, Y. Muto, S. Yokoyama, S. Inoue, Y. Inoue, Eur. J. Biochem. 1995, 228, 822.
20. L.-L. Y. Frado, J. E. Strickler, Electrophoresis 2000, 21, 2296.
21. B. Campion, D. Leger, J. M. Wieruszeski, J. Montreuil, G. Spik, Eur. J. Biochem. 1989, 184, 405.
22. V. K. Srivastava, C. Schuerch, Tetrahedron Lett. 1979, 20, 3269.
23. N. Nagashima, M. Ohno, Chem. Lett. 1987, 141.
24. J. M. Lassaletta, K. Carlsson, P. J. Garegg, R. R. Schmidt, J. Org. Chem. 1996, 61, 6873.
25. D. Qiu, R. R. Koganty, Tetrahedron Lett. 1997, 38, 961.