A strategy of "random glycosylation" for the production of oligosaccharide libraries

Angewandte Chemie (International Edition in English)

Volumn 34, Issue 23, 1996, Pages 2720-2722

  Kanie, Osamu ^a   Barresi, Frank ^a   Ding, Yili ^a   Labbe, Jill ^a   Otter, Albin ^a   Forsberg, L Scott ^b   Ernst, Beat ^c   Hindsgaul, Ole ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

^b UNIVERSITY OF GEORGIA   (United States)

^c CIBA GEIGY LTD   (Switzerland)

Author keywords

Combinatorial chemistry; Glycosylations; Oligosaccharides

Indexed keywords

EID: 33751134981     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (24)

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13. Comprehensive review of the oligosaccharides synthesized in 1994 and the methods used: g) "Glycosylation Methods in Oligosaccharide Synthesis": F. Barresi, O. Hindsgaul in Modern Synthetic Methods, Vol. 7 (Eds.: B. Ernst, C. Leuman), Helvetica Chimica Acta, Basel, 1995, pp. 281-330; h) J. Carbohydr. Chem. 1995, 14, 1043-1087. Example of highly regioselective glycosylation of a partially acceptor disaccharide containing four free OH groups: i) S. J. Danishefsky, J. Gervay, J. M. Peterson, F. E. McDonald, K. Koseki, T. Oriyama, D. A. Girffith, C. H. Wong, D. P. Dumas, J. Am. Chem. Soc. 1992, 114, 8329-8331.
14. Comprehensive review of the oligosaccharides synthesized in 1994 and the methods used: g) "Glycosylation Methods in Oligosaccharide Synthesis": F. Barresi, O. Hindsgaul in Modern Synthetic Methods, Vol. 7 (Eds.: B. Ernst, C. Leuman), Helvetica Chimica Acta, Basel, 1995, pp. 281-330; h) J. Carbohydr. Chem. 1995, 14, 1043-1087. Example of highly regioselective glycosylation of a partially acceptor disaccharide containing four free OH groups: i) S. J. Danishefsky, J. Gervay, J. M. Peterson, F. E. McDonald, K. Koseki, T. Oriyama, D. A. Girffith, C. H. Wong, D. P. Dumas, J. Am. Chem. Soc. 1992, 114, 8329-8331.
15. Comprehensive review of the oligosaccharides synthesized in 1994 and the methods used: g) "Glycosylation Methods in Oligosaccharide Synthesis": F. Barresi, O. Hindsgaul in Modern Synthetic Methods, Vol. 7 (Eds.: B. Ernst, C. Leuman), Helvetica Chimica Acta, Basel, 1995, pp. 281-330; h) J. Carbohydr. Chem. 1995, 14, 1043-1087. Example of highly regioselective glycosylation of a partially acceptor disaccharide containing four free OH groups: i) S. J. Danishefsky, J. Gervay, J. M. Peterson, F. E. McDonald, K. Koseki, T. Oriyama, D. A. Girffith, C. H. Wong, D. P. Dumas, J. Am. Chem. Soc. 1992, 114, 8329-8331.
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18. 2O (90/10).
19. 2O 91/9).
20. Methylation analysis (B. Lindberg, J. Lonngren, Methods Enzymol. 1978, 50, 3-33) was performed by the Complex Carbohydrate Research Center, University of Georgia.
21. The methylation analyses also confirmed that all six α-fucosylated trisaccharides contained a 3-O-substituted GlcNAc and a nonsubstituted Fuc residue.
22. R. U. Lemieux, K. Bock, L. T. J. Delbaere, S. Koto, V. S. Rao, Can. J. Chem. 1980, 58, 631-653.
23. In initial experiments, tetra-O-benzyl-D-galactopyranosyl trichloroacetimidate reacted with 1 to give all six possible α-galactosylated trisaccharides in ratios similar to those found in mixtures A, B, and C.
24. 4-p-OMe(n = 3, 4, and 6) were prepared on gram scale by multistep synthesis and fully characterized: Y. Ding, J. Labbe, O. Kanie, O. Hindsgaul, Bioorg. Biomed. Chem., in press.