Amphiphilic poly(sugar amino acid)s: a novel class of glycoclusters for supramolecular materials

Abstract

A poly(sugar amino acid) having self-assembling properties was efficiently synthesised by simple polymerisation of 1-O-dodecyl-2-amino-2-deoxy-β-D-glucopyranosiduronic acid 7 derived from D-glucofuranurono-6,3-lactone as the key starting material.

References

1. Synthetic Glycoconjugates, part 10. For part 9, see M. Ohmae, S. Suzuki, S. Tokura, N. Nishi and S.-I. Nishimura, J. Biochem., 1996, 119, 367.
2. Y. C. Lee and R. T. Lee, Acc. Chem. Res., 1995, 28, 321.
3. P. Arya and R. N. Ben, Angew. Chem., Int. Ed. Engl., 1997, 36, 1280 and references cited therein.
4. For leading references: D. Rouzaud and P. Sinay, J. Chem. Soc., Chem. Commun., 1983, 1353; H. Dietrich and R. R. Schmidt, Liebigs Ann. Chem., 1994, 975; T. Haneda, P. G. Goekjian, S. H. Kim and Y. Kishi, J. Org. Chem., 1992, 57, 490; H. Ishida, H. Hosokawa, H. Kondo, M. Kiso and A. Hasegawa, Carbohydr. Res., 1997, 303, 131.
5. K. C. Nicolaou, H. Florke, M. G. Egan, T. Barth and V. A. Estevez, Tetrahedron Lett., 1995, 36, 1775.
6. K. Heyns and H. Paulsen, Chem. Ber., 1995, 88, 188.
7. E.-F. Fuchs and J. Lehmann, Chem. Ber., 1975, 108, 2254.
8. J. Yoshimura, H. Ando, T. Sato and S. Tsuchida, Bull. Chem. Soc. Jpn., 1976, 49, 2511; C. Muller, E. Kitas and H. P. Wessel, J. Chem. Soc., Chem. Commun., 1995, 2425; Y. Suhara, J. E. K. Hildreth and Y. Ichikawa, Tetrahedron Lett., 1996, 37, 1575; R. A. Goodnow, S. Tam, D. L. Pruess and W. W. McComas, Tetrahedron Lett., 1997, 38, 3199; J. Gervay, T. M. Flaherty and C. Nguyen, Tetrahedron Lett., 1997, 38, 1493.
9. E. G. Von Roedern, E. Lohof, G. Hessler, M. Hoffmann and H. Kessler, J. Am. Chem. Soc., 1996, 118, 10 156.
10. S. Tokura, Y. Ikeuchi, S.-I. Nishimura and N. Nishi, Int. J. Biol. Macromol., 1983, 5, 249.
11. A polyamide containing a sugar mimetic bicyclic oxalactam has also been reported, see H. Sumitomo and K. Hashimoto, Macromolecules, 1977, 10, 1327.
12. S.-I. Nishimura and Y. C. Lee, in Structural Diversity and Functional Versatility of Polysaccharides, ed. S. Dumitriu, Marcel Dekker, NY, 1997, pp. 523–537 and references cited therein.
13. P. C. Wyss, J. Kiss and W. Arnold, Helv. Chim. Acta, 1975, 58, 204.
14. R. U. Lemieux and R. M. Ratcliffe, Can. J. Chem., 1979, 57, 1244.
15. T. Tsuda and S.-I. Nishimura, Chem. Commun., 1996, 2779.
16. J.-M. Lehn, in Supramolecular Chemistry, Concepts and Perspectives, VCH, Weinheim, 1995, p. 173.