Carbohydrate Nanotubes

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 13-14, 1997, Pages 1451-1454

  Gattuso, Giuseppe ^a   Menzer, Stephan ^b   Nepogodiev, Sergey A ^a   Stoddart, J Fraser ^a   Williams, David J ^b  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^b IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

Carbohydrates; Cyclodextrins; Oligosaccharides; Supramolecular chemistry

Indexed keywords

EID: 0030794769     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199714511     Document Type: Article

References (28)

1. Natural and semi-synthetic examples: a) higher members of the CD family such as δ-CD, ε-CD, xi-CD, and η-CD, which are composed of 9, 10, 11, and 12 D-glucopyranose repeating residues, respectively (D. French, A. O. Pulley, J. Effendberger, M. Rougvie, M. Abdullach, M., Arch. Biochem. Biophys. 1965, 111, 153-160); b) cyclic β-(1→ 2)-glucans incorporating 17 to 40 D-glucopyranose residues (M. W. Breedveld, K. Miller, Microbiol. Rev. 1994, 58, 145161); c) cyclic β-(1→ 3)-glucans with 10 repeating units (P. E. Pfeffer, S. F. Osman, A. Hotchkiss, A. A. Bhagwat, D. L. Keister, K. M. Valentine, Carbohydr. Res. 1996, 296, 23-37); d) cyclic glucans with β-(1→3) and β-(1 → 6) types of interglycosidic linkages containing more than 11 monosaccharides (N. Iñón de Iannino, R. A. Ugalde, Arch. Microbiol 1993, 159, 30-38); e) a unique microbial dodecasaccharide related to an enterobacterial common antigen (E. V. Vinogradov, Y. A. Knirel, J. Thomas-Oates, A. S. Shashkov, V. L. L'vov, Carbohydr. Res. 1994, 258, 223-232).
2. Natural and semi-synthetic examples: a) higher members of the CD family such as δ-CD, ε-CD, xi-CD, and η-CD, which are composed of 9, 10, 11, and 12 D-glucopyranose repeating residues, respectively (D. French, A. O. Pulley, J. Effendberger, M. Rougvie, M. Abdullach, M., Arch. Biochem. Biophys. 1965, 111, 153-160); b) cyclic β-(1→ 2)-glucans incorporating 17 to 40 D-glucopyranose residues (M. W. Breedveld, K. Miller, Microbiol. Rev. 1994, 58, 145161); c) cyclic β-(1→ 3)-glucans with 10 repeating units (P. E. Pfeffer, S. F. Osman, A. Hotchkiss, A. A. Bhagwat, D. L. Keister, K. M. Valentine, Carbohydr. Res. 1996, 296, 23-37); d) cyclic glucans with β-(1→3) and β-(1 → 6) types of interglycosidic linkages containing more than 11 monosaccharides (N. Iñón de Iannino, R. A. Ugalde, Arch. Microbiol 1993, 159, 30-38); e) a unique microbial dodecasaccharide related to an enterobacterial common antigen (E. V. Vinogradov, Y. A. Knirel, J. Thomas-Oates, A. S. Shashkov, V. L. L'vov, Carbohydr. Res. 1994, 258, 223-232).
3. Natural and semi-synthetic examples: a) higher members of the CD family such as δ-CD, ε-CD, xi-CD, and η-CD, which are composed of 9, 10, 11, and 12 D-glucopyranose repeating residues, respectively (D. French, A. O. Pulley, J. Effendberger, M. Rougvie, M. Abdullach, M., Arch. Biochem. Biophys. 1965, 111, 153-160); b) cyclic β-(1→ 2)-glucans incorporating 17 to 40 D-glucopyranose residues (M. W. Breedveld, K. Miller, Microbiol. Rev. 1994, 58, 145161); c) cyclic β-(1→ 3)-glucans with 10 repeating units (P. E. Pfeffer, S. F. Osman, A. Hotchkiss, A. A. Bhagwat, D. L. Keister, K. M. Valentine, Carbohydr. Res. 1996, 296, 23-37); d) cyclic glucans with β-(1→3) and β-(1 → 6) types of interglycosidic linkages containing more than 11 monosaccharides (N. Iñón de Iannino, R. A. Ugalde, Arch. Microbiol 1993, 159, 30-38); e) a unique microbial dodecasaccharide related to an enterobacterial common antigen (E. V. Vinogradov, Y. A. Knirel, J. Thomas-Oates, A. S. Shashkov, V. L. L'vov, Carbohydr. Res. 1994, 258, 223-232).
4. Natural and semi-synthetic examples: a) higher members of the CD family such as δ-CD, ε-CD, xi-CD, and η-CD, which are composed of 9, 10, 11, and 12 D-glucopyranose repeating residues, respectively (D. French, A. O. Pulley, J. Effendberger, M. Rougvie, M. Abdullach, M., Arch. Biochem. Biophys. 1965, 111, 153-160); b) cyclic β-(1→ 2)-glucans incorporating 17 to 40 D-glucopyranose residues (M. W. Breedveld, K. Miller, Microbiol. Rev. 1994, 58, 145161); c) cyclic β-(1→ 3)-glucans with 10 repeating units (P. E. Pfeffer, S. F. Osman, A. Hotchkiss, A. A. Bhagwat, D. L. Keister, K. M. Valentine, Carbohydr. Res. 1996, 296, 23-37); d) cyclic glucans with β-(1→3) and β-(1 → 6) types of interglycosidic linkages containing more than 11 monosaccharides (N. Iñón de Iannino, R. A. Ugalde, Arch. Microbiol 1993, 159, 30-38); e) a unique microbial dodecasaccharide related to an enterobacterial common antigen (E. V. Vinogradov, Y. A. Knirel, J. Thomas-Oates, A. S. Shashkov, V. L. L'vov, Carbohydr. Res. 1994, 258, 223-232).
5. Natural and semi-synthetic examples: a) higher members of the CD family such as δ-CD, ε-CD, xi-CD, and η-CD, which are composed of 9, 10, 11, and 12 D-glucopyranose repeating residues, respectively (D. French, A. O. Pulley, J. Effendberger, M. Rougvie, M. Abdullach, M., Arch. Biochem. Biophys. 1965, 111, 153-160); b) cyclic β-(1→ 2)-glucans incorporating 17 to 40 D-glucopyranose residues (M. W. Breedveld, K. Miller, Microbiol. Rev. 1994, 58, 145161); c) cyclic β-(1→ 3)-glucans with 10 repeating units (P. E. Pfeffer, S. F. Osman, A. Hotchkiss, A. A. Bhagwat, D. L. Keister, K. M. Valentine, Carbohydr. Res. 1996, 296, 23-37); d) cyclic glucans with β-(1→3) and β-(1 → 6) types of interglycosidic linkages containing more than 11 monosaccharides (N. Iñón de Iannino, R. A. Ugalde, Arch. Microbiol 1993, 159, 30-38); e) a unique microbial dodecasaccharide related to an enterobacterial common antigen (E. V. Vinogradov, Y. A. Knirel, J. Thomas-Oates, A. S. Shashkov, V. L. L'vov, Carbohydr. Res. 1994, 258, 223-232).
6. Review on synthetic cyclic oligosaccharides: G. Gattuso, S. A. Nepogodiev, J. F. Stoddart, Chem. Rev. 1997, submitted.
7. A few large ring synthetic cyclic oligosaccharides have been reported: a) N. K. Kochetkov, S.A. Nepogodiev, L. V. Backinowsky, Tetrahedron 1990, 46, 139-150; b) H. Kuyama, T. Nukada, Y. Ito, Y. Nakahara, T. Ogawa, Carbohydr. Res. 1995, 268, C1-C6; H. Driguez, J.-P. Utille, Carbohydr. Lett. 1994, 1, 125128.
8. A few large ring synthetic cyclic oligosaccharides have been reported: a) N. K. Kochetkov, S.A. Nepogodiev, L. V. Backinowsky, Tetrahedron 1990, 46, 139-150; b) H. Kuyama, T. Nukada, Y. Ito, Y. Nakahara, T. Ogawa, Carbohydr. Res. 1995, 268, C1-C6; H. Driguez, J.-P. Utille, Carbohydr. Lett. 1994, 1, 125128.
9. A few large ring synthetic cyclic oligosaccharides have been reported: a) N. K. Kochetkov, S.A. Nepogodiev, L. V. Backinowsky, Tetrahedron 1990, 46, 139-150; b) H. Kuyama, T. Nukada, Y. Ito, Y. Nakahara, T. Ogawa, Carbohydr. Res. 1995, 268, C1-C6; H. Driguez, J.-P. Utille, Carbohydr. Lett. 1994, 1, 125128.
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15. c) K. Harata in Comprehensive Supramolecular Chemistry, Vol 3 (Eds.: J. Szejtli, T. Osa), Elsevier, Oxford, 1996, pp. 279-304.
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17. T. Fujiwara, N. Tanaka, S. Kobayashi, Chem. Lett. 1990, 739-742.
18. P. R. Ashton, C. L. Brown, S. Menzer, S. A. Nepogodiev, J. F. Stoddart, D. J. Williams, Chem. Eur. J. 1996, 2, 580-591.
19. a) S.A. Nepogodiev, G. Gattuso, J. F. Stoddart in Proceedings of the 8th International Symposium on Cyclodextrins (Eds. : J. Szejtli, L. Szente), Kluwer, Dordrecht, 1996, pp. 89-94;
20. b) P. R. Ashton, S. J. Cantrill, G. Gattuso, S. Menzer, S. A. Nepogodiev, A. N. Shipway, J. F. Stoddart, D. J. Williams, Chem. Eur. J., 1997, 3, 1299-1314.
21. a) M. R. Ghadiri, K. Kobayashi, J. R. Granja, R. K. Chadha, D. E. McRee, Angew. Chem. 1995, 107, 76-78; Angew. Chem. Int. Ed. Engl. 1995, 34, 93-95;
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28. 2. All computations were carried out with the SHELXTL 5.03 package. The crystallographic data (excluding structure factors) for the structure reported in this paper has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-100130. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB21EZ, UK deposit@chemcrys.cam.ac.uk