Efficient synthesis of glycosylated asparaginic acid building blocks via click chemistry

Synthesis

Volumn , Issue 4, 2008, Pages 0519-0526

  Pietrzik, Nikolas ^a   Schips, Carsten ^a   Ziegler, Thomas ^a  

^a UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

1,3 dipolar cycloadditions; Amino acids; Azides; Carbohydrates; Glycopeptides; Glycosides; Heterocycles

Indexed keywords

AMIDES; BIOSYNTHESIS; CARBOHYDRATES; CYCLOADDITION; GLYCOPROTEINS;

AMINOBUTYRIC ACIDS; GLYCOSIDES; HETEROCYCLES;

AMINO ACIDS;

AMINO ACID; AMINOBUTYRIC ACID DERIVATIVE; ASPARTIC ACID; AZIDE; CARBOHYDRATE; COPPER; GLYCOPEPTIDE; GLYCOSIDE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL STRUCTURE; CYCLOADDITION; GLYCOSYLATION; MICROWAVE IRRADIATION; ONE POT SYNTHESIS; PROTEIN CARBOHYDRATE INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 39749084583     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1032150     Document Type: Article

References (34)

1. Ziegler, T.; Röseling, D.; Subramanian, L. R. Tetrahedron: Asymmetry 2002, 13, 911.
2. Schips, C.; Ziegler, Th. J. Carbohydr. Chem. 2005, 24, 773.
3. Ziegler, T. h.; Schips, C. DE Patent 102004046010, 2005; Chem. Abstr. 2005, 144, 1282957.
4. Ziegler, Th.; Schips, C. Nature: Protocols 2006, 1, 1987.
5. Huisgen, R.; Knorr, R.; Möbius, L.; Szeimies, G. Chem. Ber. 1965, 98, 4014.
6. Sharpless, K. B.; Fokin, V. V.; Green, L. G.; Rostovtsev, V. V. Angew. Chem. Int. Ed. 2002, 41, 2596.
7. Meldal, M.; Christensen, C.; Tornoe, C. W. J. Org. Chem. 2002, 67, 3057.
8. Bock, V. D.; Hiemstra, H.; van Maarseveen, J. H. Eur. J. Org. Chem. 2006, 51.
9. Dedola, S.; Nepogodiev, S. A.; Field, R. A. Org. Biomol. Chem. 2007, 5, 1006.
10. Winkinson, B. L.; Bornaghi, L. F.; Poulson, A.-A.; Houston, T. A. Tetrahedron 2006, 62, 8115.
11. Fernandez-Megia, E.; Correa, J.; Rodriguez-Meizoso, I.; Riguera, R. Macromolecules 2006, 39, 2113.
12. Perion, R.; Ferneres, V.; Garcia-Moreno, M. I.; Mellet, C. O.; Duval, R.; Fernandez, J. M. G.; Plusquellec, D. Tetrahedron 2005, 61, 9118.
13. Bodine, K. D.; Gin, D. Y.; Gin, M. S. Org. Lett. 2005, 7, 4479.
14. Dörner, S.; Westermann, B. Chem. Commun. 2005, 2852.
15. Casas-Solvas, J. M.; Vargas-Berenguel, A.; Capitan-Vallvey, L. F.; Santoyo-Gonzales, F. Org. Lett. 2004, 6, 3687.
16. Hoffmann, B.; Bernet, B.; Vasella, A. Helv. Chim. Acta 2002, 85, 265.
17. Seki, M. Synthesis 2006, 2975.
18. Dos Anjos, J. V.; Sinou, D.; de Melo, S. J.; Srivastava, R. M. Synthesis 2007, 2647.
19. Angell, Y. L.; Burgess, K. Chem. Soc. Rev. 2007, 36, 1674.
20. Boeijen, A.; van Ameijde, J.; Liskamp, R. M. J. J. Org. Chem. 2001, 66, 8454.
21. Gan, Z.; Roy, R. Tetrahedron Lett. 2000, 41, 1155.
22. Kaufmann, R. J.; Sidhu, R. S. J. Org. Chem. 1982, 47, 4941.
23. Ibatullin, F. M.; Shabalin, K. A. Synth. Commun. 2000, 30, 2819.
24. Jiang, J.; Biggins, J. B.; Thorson, J. S. Angew. Chem. Int. Ed. 2001, 40, 1502.
25. Kerekgyarto, J.; Szurmai, Z.; Liptak, A. Carbohydr. Res. 1993, 245, 65.
26. Skelton, B. W.; Stick, R. V.; Tilbrook, D. M. G.; White, A. H.; Williams, S. J. Aust. J. Chem. 2000, 53, 389.
27. Perez-Balderas, F.; Ortega-Munoz, M.; Morales-Sanfrutos, J.; Hernandez-Mateo, F.; Calvo-Flores, F. G.; Calvo-Asin, J. A.; Isac-Garcia, J.; Santoyo-Gonzales, F. Org. Lett. 2003, 5, 1951.
28. Gamblin, D. P.; Garnier, P.; van Kasteren, S.; Oldham, N. J.; Fairbanks, A. J.; Davis, B. G. Angew. Chem. Int. Ed. 2004, 43, 828.
29. Fujihira, T.; Chida, M.; Kamijo, H.; Takido, T.; Seno, M. J. Carbohydr. Chem. 2002, 21, 287.
30. Matta, K. L.; Girotra, R. N.; Barlow, J. J. Carbohydr. Res. 1975, 43, 101.
31. Meng, X.-B.; Yang, L.-D.; Li, H.; Li, Q.; Cheng, T.-M.; Cai, M.-S.; Li, Z.-J. Carbohydr. Res. 2002, 337, 977.
32. Horton, D.; Wolfrom, M. L. J. Org. Chem. 1962, 27, 1794.
33. Dasgupta, F.; Garregg, P. J. Acta Chem. Scand. 1989, 43, 471.
34. Koto, S.; Yoshid, T.; Takenaka, K.; Zen, S. Bull Chem. Soc. Jpn. 1982, 55, 3667.