Synthesis and structural characterization of 6I,6II-diamino-6I,6 II-dideoxy-cyclomaltoheptaose, a difunctionalized β-cyclodextrin

Carbohydrate Research

Volumn 282, Issue 1, 1996, Pages 41-52

  Di Blasio, Benedetto ^a,b   Galdiero, Stefania ^b   Saviano, Michele ^b   Pedone, Carlo ^b   Benedetti, Ettore ^b   Rizzarelli, Enrico ^c,d   Pedotti, Sonia ^d   Vecchio, Graziella ^d   Gibbons, William A ^e  

^a UNIVERSITY OF BASILICATA   (Italy)

^b UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^c UNIVERSITY OF CATANIA   (Italy)

^d CNR   (Italy)

^e UNIVERSITY OF LONDON   (United Kingdom)

Author keywords

Crystal structure; Cyclodextrins; Cyclomaltoheptaose; Difunctionalized cyclodextrin

Indexed keywords

BETA CYCLODEXTRIN DERIVATIVE;

ARTICLE; CRYSTALLOGRAPHY; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

BETA-CYCLODEXTRINS; CARBOHYDRATE SEQUENCE; CYCLODEXTRINS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; OPTICAL ROTATION; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT; X-RAY DIFFRACTION;

EID: 0030030846     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/0008-6215(95)00357-6     Document Type: Article

References (41)

1. M. Bender and M. Komiyama, Cyclodextrin Chemistry, Springer, Berlin, 1978.
2. J. Szejtli, Cyclodextrin Technology, Kluwer Academic, Dordrecht, 1988.
3. W. Saenger, Angew. Chem., Int. Ed. Engl., 19 (1980) 344-362.
4. R.J. Clarke, J.H. Coates, and S.F. Lincoln, Adv. Carbohydr. Chem. Biochem., 46 (1988) 205-249.
5. V.T. D'Souza and M.L. Bender, Acc. Chem. Res., 20 (1987) 146-152.
6. L. Jullien, J. Canceill, B. Valeur, E. Bardez, and J.M. Lehn, Angew. Chem., Int. Ed. Engl., 33 (1994) 2438-2439.
7. I. Tabushi, Y. Kuroda, and T. Mizutani, J. Am. Chem. Soc., 108 (1986) 4514-4518.
8. K. Jsujihara, H. Kurita, and M. Kawazu, Bull. Chem. Soc. Jpn., 50 (1977) 1571-1576.
9. S.E. Brown, J.H. Coates, P.A. Durkworth, S.F. Lincoln, C.J. Easton, and B.L. May, J. Chem. Soc., Faraday Trans., 89 (1993) 1035-1040.
10. A.V. Eliseev and H.-J. Schneider, J. Am. Chem. Soc., 116 (1994) 6081-6088.
11. A.K. Yatsimirskii and A.V. Eliseev, J. Chem. Soc., Perkin Trans. 2, (1991) 1769-1865.
12. M. Yashiro, S. Miyama, T. Takarada, and M. Komiyama, J. Inclus. Phenom., 17 (1994) 393-397.
13. P. Klufers and J. Schuhmacher, Angew. Chem., Int. Ed. Engl., 33 (1994) 1863-1865.
14. R. Fuchs, N. Habermann, and P. Klufers, Angew. Chem., Int. Ed. Engl., 32 (1993) 852-858.
15. J. Szejtli, Staerke, 42 (1990) 444-447, and references therein.
16. I. Tabushi, Coord. Chem. Rev., 86 (1988) 1-42.
17. R. Breslow and L. Overman, J. Am. Chem. Soc., 92 (1970) 1075-1077.
18. I. Tabushi, N. Shimizu, T. Sugimoto, M. Shiozuka, and K. Yamamura, J. Am. Chem. Soc., 99 (1977) 7100-7102.
19. G. Maccarrone, E. Rizzarelli, and G. Vecchio, in L. Fabbrizi and A. Poggi (Eds.), Transition Metals in Supramolecular Chemistry, Kluwer Academic, Dordrecht, 1994, pp 351-370.
20. R. Corradini, A. Dossena, G. Impellizzeri, G. Maccarrone, R. Marchelli, E. Rizzarelli, G. Sartor, and G. Vecchio, J. Am. Chem. Soc., 116 (1994) 10267-10274.
21. S.E. Brown, J.H. Coates, C.J. Easton, and S.F. Lincoln, J. Chem. Soc., Faraday Trans., 90 (1994) 739-743.
22. V. Cucinotta, F. D'Alessandro, G. Impellizzeri, and G. Vecchio, J. Chem. Soc., Chem. Commun., (1992) 1743-1745.
23. R.P. Bonomo, V. Cucinotta, F. D'Alessandro, G. Impellizzeri, G. Maccarrone, E. Rizzarelli, and G. Vecchio, J. Incl. Phenom., 15 (1993) 167-180.
24. I. Tabushi, K. Shimokawa, and K. Fujita, Tetrahedron Lett., 18 (1977) 1527-1530.
25. I. Tabushi, T. Nabeshima, K. Fujita, A. Matsunaga, and T. Imoto, J. Org. Chem., 50 (1985) 2638-2643.
26. V. Cucinotta, F. D'Alessandro, G. Impellizzeri, and G. Vecchio, Carbohydr. Res., 224 (1992) 95-102.
27. H Parrot-Lopez, H. Galons, S. Dupas, M. Miocque, and G. Tsoucaris, Bull. Soc. Chim. Fr., 127 (1990) 568-571.
28. G.M. Sheldrick, SHELX 76: Programs for Crystal Structure Determination, University of Cambridge, UK, 1975.
29. E. Egert and G.M. Sheldrick, Acta Crystallogr., Sect. A, 41 (1985) 262-268.
30. G. Germain, P. Main, and M.M. Woolfson, Acta Crystallogr., Sect. A, 27 (1971) 368-376.
31. A. Altomare, M.C. Burla, M. Camalli, G. Cascarano, C. Giacovazzo, C. Gugliardi, and G. Polidori, J. Appl. Cryst., (1994) 435.
32. R.P. Bonono, B. Di Blasio, G. Maccarone, V. Pavone, C. Pedone, E. Rizzarelli, M. Saviano, and G. Vecchio, J. Inorg. Biochem., submitted for publication.
33. E. Egert, Acta Crystallogr., Sect. A, 39 (1983) 936.
34. B.A. Frenk, and Associated Int., Structure Determination Package, A System of Computer Programs, College Station, TX, and Enraf-Nonius, Delft, Holland, 1986.
35. D.T. Cromer and J.T. Waber, International Tables for X-Ray Crystallography, Vol. 4, Kynoch, Birmingham 1974, Table 2.2B, p 99.
36. D. Cremer and J.A. Pople, J. Am. Chem. Soc., 97 (1975) 1354-1358.
37. B. Di Blasio, V. Pavone, F. Nastri, C. Isernia, M. Saviano, C. Pedone, V. Cucinotta, G. Impellizzeri, E. Rizzarelli, and G. Vecchio, Proc. Natl. Acad. Sci. USA, 89 (1992) 7218-7221.
38. P.C. Jones and A.J. Kirby, J. Chem. Soc., Chem. Commun., (1979) 288-289.
39. P.O. Jones and A.J. Kirby, J. Am. Chem. Soc., 106 (1984) 6207-6212.
40. G. Condorelli, L.L. Costanzo, G. De Guidi, S. Giuffrida, E. Rizzarelli, and G. Vecchio, J. Inorg. Biochem., 54 (1994) 257-265.
41. V. Cucinotta, A. Mangano, G. Nobile, A.M. Santoro, and G. Vecchio, J. Inorg. Biochem., 52 (1993) 183-190.