Trehalose-based octopus glycosides for the synthesis of carbohydrate-centered PAMAM dendrimers and thiourea-bridged glycoclusters

Organic Letters

Volumn 3, Issue 25, 2001, Pages 4019-4022

  Dubber, Michael ^a   Lindhorst, Thisbe K ^a  

^a UNIVERSITY OF KIEL   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDE; POLYAMINE; THIOUREA; TREHALOSE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

GLYCOSIDES; MOLECULAR STRUCTURE; POLYAMINES; SUPPORT, NON-U.S. GOV'T; THIOUREA; TREHALOSE;

EID: 0035856932     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016717o     Document Type: Article

References (41)

1. (a) Matthews, O. A.; Shipway, A. N.; Stoddart, J. F. Prog. Polym. Sci. 1998, 23, 1-56.
2. (b) Vögtle, F.; Fischer, M. Angew. Chem. 1999, 111, 934-955; Angew. Chem., Int. Ed. 1999, 38, 884-905.
3. (b) Vögtle, F.; Fischer, M. Angew. Chem. 1999, 111, 934-955; Angew. Chem., Int. Ed. 1999, 38, 884-905.
4. (c) Hecht, S.; Fréchet, J. M. J. Angew. Chem. 2001, 113, 76-94; Angew. Chem., Int. Ed. 2001, 40, 74-91.
5. (c) Hecht, S.; Fréchet, J. M. J. Angew. Chem. 2001, 113, 76-94; Angew. Chem., Int. Ed. 2001, 40, 74-91.
6. Tomalia; D. A.; Baker, H.; Dewald, J. R. Polym. J. 1985, 17, 117-132.
7. Tang, M. X.; Redemann, C. T.; Szoka, F. C. Bioconjugate Chem. 1996, 7, 703-714.
8. Dubber, M.; Lindhorst, Th. K. Chem. Commun. 1998, 1265-1266.
9. Dubber, M.; Lindhorst, Th. K. Carbohydr. Res. 1998, 310, 35-41.
10. Newkome, G. R.; Lin, X.; Young, J. K. Synlett 1992, 53-54.
11. (a) Moors, R. Vögtle, F. Chem. Ber. 1993, 126, 2133-2135.
12. (b) Wörner, C.; Mülhaupt, R. Angew. Chem. 1993, 105, 1367-1369, Angew. Chem., Int. Ed. Engl. 1993, 32, 1306-1308.
13. (b) Wörner, C.; Mülhaupt, R. Angew. Chem. 1993, 105, 1367-1369, Angew. Chem., Int. Ed. Engl. 1993, 32, 1306-1308.
14. (c) de Brabander-van den Berg, E. M. M.; Meijer, E. W. Angew. Chem. 1993, 105, 1370; Angew. Chem., Int. Ed. 1993, 32, 1308.
15. (c) de Brabander-van den Berg, E. M. M.; Meijer, E. W. Angew. Chem. 1993, 105, 1370; Angew. Chem., Int. Ed. 1993, 32, 1308.
16. Dubber, M.; Lindhorst, Th. K. J. Org. Chem. 2000, 65, 5275-5281.
17. Appel, R. Angew. Chem. 1975, 87, 863-874; Angew. Chem., Int. Ed. Engl. 1975, 14, 801-811.
18. Appel, R. Angew. Chem. 1975, 87, 863-874; Angew. Chem., Int. Ed. Engl. 1975, 14, 801-811.
19. Gabson, M. S.; Bradshaw, R. W. Angew. Chem. 1968, 80, 986-496; Angew. Chem., Int. Ed. Engl. 1968, 7, 919-929.
20. Gabson, M. S.; Bradshaw, R. W. Angew. Chem. 1968, 80, 986- 496; Angew. Chem., Int. Ed. Engl. 1968, 7, 919-929.
21. Essentials of Glycobiology; Varki, A., Cummings, R., Esko, J., Freeze, H., Hart, G., Marth, J., Eds.; Cold Spring Harbour Laboratory Press: Spring Harbor, Plainview, NY, 1999.
22. Lindhorst, Th. K.; Kieburg, C.; Krallmann-Wenzel, U. Glycoconjugate J. 1998, 15, 605-613.
23. (a) Roy, R. TIGG 1996, 8, 79-99.
24. (b) Roy, R. Curr. Opin. Struct. Biol. 1996, 6, 692-702.
25. (c) Zanini, D.; Roy, R. In Carbohydrate Mimics, Concepts und Methods; Chapleur, Y., Ed.; Wiley-VCH: Weinheim, Germany, 1998; pp 385-415.
26. (d) Roy, R. Carbohydr. Eur. 1999, 27, 34-41.
27. (e) Jayaraman, N.; Nepogodiev, S. A.; Stoddart, J. F. Chem. Eur. J. 1997, 3, 1193-1199.
28. (f) Ashton, P. R.; Hounsell, E. F.; Jayaraman, N.; Nilsen, T. M.; Spencer, N.; Stoddart, J. F. J. Org. Chem. 1998, 63, 3429-3437.
29. (g) Turnbull, W. B.; Pease, A. R.; Stoddart J. F. ChemBioChem 1998, 1, 70-74.
30. (h) Kitov, P. I.; Sadowska, J. M. M.; Mulvey, G.; Amstrong, G. D.; Ling, H.; Pannu, N. S.; Read, R. J.; Bundle, D. R. Nature 2000, 403, 669-672.
31. (i) Fan, E.; Zhang, Z.; Minke, W. E.; Hou, Z.; Verlinde, C. L. M. J.; Hol, W. G. J. J. Am. Chem. Soc. 2000, 122, 2663-2664.
32. (a) Lee, Y. C.; Lee, R. T. Acc. Chem. Res. 1995, 28, 321-327.
33. (b) Kiessling, L. L.; Pohl, N. L. Chem. Biol. 1996, 3, 71-77.
34. (c) Mammen, M.; Choi, S.-K.; Whitesides, G. M. Angew. Chem. 1998, 110, 2908-2953; Angew. Chem., Int. Ed. 1998, 37, 2754-2794.
35. (c) Mammen, M.; Choi, S.-K.; Whitesides, G. M. Angew. Chem. 1998, 110, 2908-2953; Angew. Chem., Int. Ed. 1998, 37, 2754-2794.
36. (d) Bertozzi, C. R.; Kiessling, L. L. Science 2001, 291, 2357-2364.
37. (a) Lindhorst, Th. K.; Kieburg, C. Angew. Chem. 1996, 108, 2083-2086; Angew. Chem., Int. Ed. Engl. 1996, 35, 1953-1956.
38. (a) Lindhorst, Th. K.; Kieburg, C. Angew. Chem. 1996, 108, 2083- 2086; Angew. Chem., Int. Ed. Engl. 1996, 35, 1953-1956.
39. (b) Pagé, D.; Roy, R. Bioconjugate Chem. 1997, 8, 714-723.
40. (c) Ortiz-Mellet, C.; Benito, J. M.; García Fernández, J. M.; Law, H.; Chmurski, K.; Defaye, J.; O'Sullivan, M. L.; Caro, H. N. Chem. Eur. J. 1998, 4, 2523-2531.
41. de Santiago, R.; Fernández-Mayoralas, A.; García-Junceda, E. J. Mol. Catal. B: Enzym. 2000, 11, 71-79.