A convenient preparation of several N-linked glycoamino acid building blocks for efficient solid-phase synthesis of glycopeptides

Journal of the Chemical Society. Perkin Transactions 1

Volumn 2, Issue 8, 2002, Pages 1042-1049

  Van Ameijde, Jeroen ^a   Albada, H Bauke ^a   Liskamp, Rob M J ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CARBOHYDRATES; COLLAGEN; COLUMN CHROMATOGRAPHY; ESTERS; METHANOL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS (CHEMICAL);

SOLID-PHASE SYNTHESIS;

MONOMERS;

EID: 0037150006     PISSN: 14727781     EISSN: 13645463     Source Type: Journal    
DOI: 10.1039/b201296k     Document Type: Article

References (32)

1. H.B.A. De Bont, G.H. Veeneman, J.H. Van Boom, R.M.J. Liskamp Recl. Trav. Chim. Pays-Bas 1987, 106, 641.
2. H.B.A. De Bont, R.M.J. Liskamp, C.A. O’Brian, C. Erkelens, G.H. Veeneman, J.H. Van Boom Int. J. Pept. Protein Res. 1989, 33, 115.
3. A. van Oijen, C. Erkelens, J.H. van Boom, R.M.J. Liskamp J. Am. Chem. Soc. 1989, 111, 9103.
4. H.B.A. De Bont, J.H. Van Boom, R.M.J. Liskamp Tetrahedron Lett. 1990, 31, 2497.
5. H.B.A. de Bont, W.J. Moree, J.H. van Boom, R.M.J. Liskamp J. Org. Chem. 1993, 58, 1309.
6. A.H. van Oijen, S. Behrens, D.F. Mierke, H. Kessler, J.H. van Boom, R.M.J. Liskamp J. Org. Chem. 1993, 58, 3722.
7. A.K.M. Anisuzzman, L. Anderson, J.L. Navia Carbohydr. Res. 1988, 174, 265.
8. D.T. Osuga, M.S. Feather, M.J. Shah, R.E. Feeney J. Protein Chem. 1989, 8, 519.
9. F. Filira, L. Biondi, B. Scolaro, M.T. Foffani, S. Mammi, E. Peggion, R. Rocchi Int. J. Biol. Macromol. 1990, 12, 4.
10. T. Tsuda, S.-I. Nishimura Chem. Commun. 1996, 2779.
11. W.-T. Jiaang, K.-F. Hsiao, S.-T. Chen, K.-T. Wang Synthesis 1999, 1687.
12. R.N. Ben, A.A. Eniade, L. Hauer Org. Lett. 1999, 1, 1759.
13. P.-H. Tseng, W.-T. Jiaang, M.-Y. Chang, S.-T. Chen Chem. Eur. J. 2001, 7, 585.
14. A.A. Eniade, R.N. Ben Biomacromolecules 2001, 2, 557.
15. H.P. Bächinger, J.G. Bann, D.H. Peyton FEBS Lett. 2000, 473, 237.
16. H.P. Bächinger, J.G. Bann J. Biol. Chem. 2000, 275, 24466.
17. H. Nikaido J. Biol. Chem. 1994, 269, 3905.
18. P.E. Klebba, S.M.C. Newton Curr. Opin. Microbiol. 1998, 1, 238.
19. M.J. Chrispeels, N.M. Crawford, J.I. Schroeder Plant Cell 1999, 11, 661.
20. E. Meinjohanns, M. Meldal, H. Paulsen, R.A. Dwek, K. Bock J. Chem. Soc., Perkin Trans. 1 1998, 549.
21. H. Kunz Angew. Chem., Int. Ed. Engl. 1987, 26, 294.
22. H. Kunz, C. Unverzagt Angew. Chem., Int. Ed. Engl. 1988, 27, 1697.
23. D.M. Gordon, S.J. Danishefsky J. Org. Chem. 1991, 56, 3713.
24. L. Urgge, L. Otvos, E. Lang, K. Wroblewski, I. Laczko, M. Hollosi Carbohydr. Res. 1992, 235, 83.
25. T. Teshima, K. Nakajima, M. Takahashi, T. Shiba Tetrahedron Lett. 1992, 33, 363.
26. L.A. Handlon, B. Fraser-Reid J. Am. Chem. Soc. 1993, 115, 3796.
27. C. Srinivas Rao, A.J. Ratcliffe, B. Fraser-Reid J. Chem. Soc., Perkin Trans. 1 1993, 1207.
28. M. Mizuno, I. Muramoto, K. Katsuaki, H. Yaginuma, T. Inazu Synthesis 1999, 162.
29. S. Ogawa, R. Sekura, A. Maruyama, H. Yuasa, H. Hashimoto Eur. J. Org. Chem. 2000, 2089.
30. J. Isac-Garcia, F.G. Calvo-Flores, F. Hernández-Mateo, F. Santoyo-González Eur. J. Org. Chem. 2001, 383.
31. C.J. Bosques, V.W.-F. Tai, B. Imperiali Tetrahedron Lett. 2001, 42, 7207.
32. E.D. Soli, M.C. Manoso, M.C. Patterson, J. DeShong J. Org. Chem. 1999, 64, 3171.