Solution phase synthesis of (1→5)-amide linked sugar amino acid dimers derived from sialic acids

Tetrahedron Letters

Volumn 38, Issue 9, 1997, Pages 1493-1496

  Gervay, Jacquelyn ^a   Flaherty, Terrence M ^a   Nguyen, Can ^a  

^a University of Arizona   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; SUGAR;

ARTICLE; CHEMICAL MODIFICATION; DRUG SYNTHESIS; HYDROGENATION; REACTION ANALYSIS;

EID: 0031550819     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00138-X     Document Type: Article

References (27)

1. 1. Several different terms have been used to describe these compounds including sugar amino acids, carbopeptoids, sugar-like amino carboxylic acids, saccharide-peptide hybrids, and saccharopeptides. In some cases the sugar amino acids are linked to naturally occurring amino acids, whereas in other examples they are completely carbohydrate derived. In order to readily distinguish between these two possibilities we would like to propose that terms including "peptide" be reserved for classes of molecules containing amino acids common in proteins and that the linkage between carbohydrate derived amino acids be referred to as an amide bond.
2. 2. For leading references see: Knapp, S. Chem. Rev. 1995, 95, 1859.
3. 3. McDevitt, J.P.; Lansbury, P.T. J. Am Chem. Soc. 1996, 118, 3818.
4. 4. (a) Graf von Roedern, E.; Lohof, E.; Hessler, G.; Hoffmann, M.; Kessler, H. J. Am. Chem. Soc. 1996, 118, 10156.
5. (b) Suhara, Y.; Hildreth, J.E.K.; Ichikawa, Y. Tetrahedron Lett. 1996, 37, 1575.
6. (c) Suhara, Y.; Ichikawa, M.; Hildreth, J.E.K.; Ichikawa, Y. Tetrahedron Lett. 1996, 37, 2549.
7. (d) Muller, C.; Kitas, E.; Wessel, H.P. J. Chem. Soc. Chem. Comm. 1995, 2425.
8. (e) Wessel, H.P.; Mitchell, C.; Lobota, C.M.; Schmid, G. Angew. Chem. Int. Ed. Engl. 1995, 34, 2712.
9. (f) Nicolaou, K.C.; Florke, H.; Egan, M.G.; Barth, T.; Estevez, V.A. Tetrahedron Lett. 1995, 36, 1775.
10. (g) Graf von Roedern, E.; Kessler, H. Angew. Chem. Int. Ed. Engl. 1994, 33, 687.
11. (h) Poitout, L.; Merrer, Y.L.; Depezay, J.-C. Tetrahedron Lett. 1995, 36, 6887.
12. (i) Apostolopoulos, C.D.; Couladouras, E.A.; Georgiadis, M.P. Liebigs Ann. Chem. 1994, 781.
13. (j) Yoshimura, J.; Ando, H.; Sato, T.; Tsuchida, S.; Hashimoto, H. Bull. Chem. Soc. Jpn. 1976, 49, 2511.
14. 5. Schreiner, E.; Zbiral, E.; Kleineidam, R.G.; Schauer, R. Liebigs Ann. Chem. 1991, 129.
15. 6.(a) Michon, F.; Brisson, J.; Jennings, H. J. Biochemistry 1987, 26, 8399-8405.
16. (b) Yamasaki, R.; Bacon, B. Biochemistry 1991, 30, 851-857.
17. 7. Schmid, W.; Christian, R.; Zbiral, E. Tetrahedron Lett. 1988, 29, 3643.
18. 8. Yu, R.K.; Ledeen, R.J. J. Biol. Chem. 1969, 244, 1306.
19. 9. Driguez, P.-A.; Barrere, B.; Quash, G.; Doutheau, A. Carbohydr. Res. 1994, 262, 297.
20. 10. Roy, R.; Pon, R.A. Glycoconjugate J. 1990, 7, 3.
21. 11. Wallimann, K.; Vasella, A. Helv. Chim. Acta 1991, 74, 1520.
22. 12. Hanessian, S. Tetrahedron Lett. 1967,16, 1549.
23. 13. Grehn, L.; Gunnarsson, K.; Ragnarsson, U. J. Chem. Soc., Chem. Commun. 1985, 1317.
24. 14. Flynn, D.L.; Zelle, R.E.; Grieco, P.A. J. Org. Chem. 1983, 48, 2424.
25. 15. Ratcliff, M.R.; Venot, A.P.; Abbas, Z.S.; Eur. Pat. Appl. EP 319,253 (Chem. Abstr. 1990, 112, 175281a).
26. 15. Ratcliff, M.R.; Venot, A.P.; Abbas, Z.S.; Eur. Pat. Appl. EP 319,253 (Chem. Abstr. 1990, 112, 175281a).
27. 16. Claesson, A.; Luthman, K.; Acta. Chem. Scand. B 1982, 36, 731.