Highly regioselective synthesis of a 3-O-sulfonated arabino Lewisa asparagine building block suitable for glycopeptide synthesis

Carbohydrate Research

Volumn 341, Issue 10, 2006, Pages 1597-1608

  Rösch, Alexander ^a   Kunz, Horst ^a  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

E Selectin ligand; Glycopeptides; Regioselective sulfonation; Sulfatyl Lewisa

Indexed keywords

CARBOHYDRATES; CATALYSIS; SYNTHESIS (CHEMICAL);

E-SELECTIN LIGAND; GLYCOPEPTIDES; REGIOSELECTIVE SULFONATION;

POLYPEPTIDES;

ALKENE; ASPARAGINE DERIVATIVE; ASPARTIC ACID; AZIDE; FLUORIDE; GLYCOPEPTIDE; TRISACCHARIDE;

ALLYLATION; ARTICLE; CATALYSIS; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; REDUCTION; SOLID; SULFONATION;

ASPARAGINE; CARBOHYDRATE SEQUENCE; GLYCOPEPTIDES; GLYCOSYLATION; MOLECULAR SEQUENCE DATA; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; OLIGOPEPTIDES; OLIGOSACCHARIDES; STEREOISOMERISM;

EID: 33646925481     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2006.03.003     Document Type: Article

References (41)

1. Bevilacqua M.P., Butcher E., Furie B., Gallatin M., Gimbrone M., Harlan J., Kishimoto K., Lasky L., McEver R.P., Paulson J.C., Rosen S.D., Seed B., Spiegelman M., Springer T.A., Stoolman L., Tedder T., Varki A., Wagner D., Weissmann I., and Zimmerman G. Cell 67 (1991) 233
2. Phillips M.L., Nudelman E., Gaeta F.C.A., Perez M., Singhal A.K., Hakamori S., and Paulson J.C. Science 250 (1990) 1130-1132
3. Walz G., Aruffo A., Kolanus W., Becilacqua M.P., and Seed B. Science 250 (1990) 1132-1135
4. Lowe J.B., Stoolman L.M., Nair R.P., Larsen R.D., Behrend T.L., and Marks R.M. Cell 63 (1990) 475-482
5. Yuen C.-T., Lawson A.M., Chai W., Larkin M., Stoll M.S., Stuart A., Sullivan F.X., Ahern T.J., and Feizi T. Biochemistry 31 (1992) 9126-9131
6. Yuen C.-T., Bezouška K., O'Brien J., Stoll M., Lemoine R., Lubineau A., Kiso M., Hasegawa A., Bockovich N.J., Nicolaou K.C., and Feizi T. J. Biol. Chem. 269 (1994) 1595-1598
7. Sprengard U., Kretzschmar G., Bartnik E., Hüls C., and Kunz H. Angew. Chem., Int. Ed. Engl. 34 (1995) 990-993
8. Sprengard U., Schudok M., Schmidt W., Kretzschmar G., and Kunz H. Angew. Chem., Int. Ed. 35 (1996) 321-324
9. Levinovitz A., Mühlhoff J., Isenman S., and Vestweber D. J. Cell. Biol. 121 (1993) 449-459
10. Rösch M., Herzner H., Dippold W., Wild M., Vestweber D., and Kunz H. Angew. Chem., Int. Ed. 40 (2001) 3836-3839
11. Hartung W.H., and Simonoff R. Org. React. VII (1953) 263-326
12. Heathcock C.H., and Ratcliffe R. J. Am. Chem. Soc. 93 (1971) 1746-1757
13. Wagner M., and Kunz H. Angew. Chem., Int. Ed. 41 (2002) 317-321
14. Wagner M., Dziadek S., and Kunz H. Chem. Eur. J. 9 (2003) 6018-6030
15. Peilstöcker K., and Kunz H. Synlett 6 (2000) 820-822;
16. Peilstöcker, K. Ph.D. Thesis, University of Mainz, 1999.
17. Unverzagt C., and Kunz H. J. Prakt. Chem. 334 (1992) 570-578
18. Paulsen H., Rauwald W., and Weichert U. Liebigs Ann. Chem. (1988) 75-86
19. Lönn H. Carbohydr. Res. 139 (1985) 105-113
20. Johnson S.W., and Alhadeff J.A. Comp. Biochem Physiol. Part B 99 (1991) 479-488
21. Simanek E.E., McGarvey G.J., Jablonowski J.A., and Wong C.H. Chem. Rev. 98 (1998) 833-862
22. Kunz H., and Unverzagt C. Angew. Chem., Int. Ed. 27 (1988) 1697-1699
23. Kunz H., and März J. Synlett (1992) 589-590
24. Montero J.L., Winum J.Y., Leydet A., Kamal M., Pavia A.A., and Roque J.P. Carbohydr. Res. 297 (1997) 175-180
25. Helferich B., and Wedemeyer K.F. Liebigs Ann. Chem. 563 (1949) 139-145
26. Schmidt R.R., and Michel J. Angew. Chem., Int. Ed. 19 (1980) 731-732
27. Sakagami M., and Hamana H. Tetrahedron Lett. 41 (2000) 5547-5551
28. Garegg P.J., Hultberg H., and Wallin S. Carbohydr. Res. 108 (1982) 97-101
29. Sato S., Ito Y., and Ogawa T. Carbohydr. Res. 155 (1986) c6-c10
30. Lemieux R.U., and Haymi J.I. Can. J. Chem. 43 (1965) 2162-2173
31. Lemieux R.U., Hendriks K.B., Stick R.V., and James K. J. Am. Chem. Soc. 97 (1975) 4056-4062
32. Lubineau A., and Lemoine R. Tetrahedron Lett. 35 (1994) 8795-8796
33. Wagner D., Verheyden J.P.H., and Moffat J.G. J. Org. Chem. 39 (1974) 24-30
34. Stahl W., Sprengard U., Kretzschmar G., Schmidt D.W., and Kunz H. J. Prakt. Chem. 337 (1995) 441-445
35. Kunz H., Pfrengle W., Rück K., and Sager W. Synthesis (1991) 1039-1042
36. Trezeciak A., and Bannwarth W. Tetrahedron Lett. 33 (1992) 4557-4560
37. Carpino L.A. J. Am. Chem. Soc. 115 (1993) 4397-4398
38. Kunz H., and Waldmann H. Angew. Chem., Int. Ed. 23 (1984) 71-72
39. Honda M., Morita H., and Nagakura I. J. Org. Chem. 62 (1997) 8932-8936
40. Ciommer M., and Kunz H. Synlett (1991) 593-595
41. Perkin Elmer ABI 433A (Applied Biosystems).