Molecular Recognition. 5.1 Molecular Recognition of Sugars via Hydrogen-Bonding Interaction with a Synthetic Polyhydroxy Macrocycle2

Journal of the American Chemical Society

Volumn 111, Issue 14, 1989, Pages 5397-5404

  Aoyama, Yasuhiro ^a   Tanaka, Yasutaka ^a   Sugahara, Shuji ^a  

^a NAGAOKA UNIVERSITY OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845185125     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00196a052     Document Type: Article

References (15)

1. Part 4 of this series: Aoyama, Y.; Uzawa, T.; Saita, K.; Tanaka, Y.; Toi, H.; Ogoshi, H.; Okamoto, Y. Tetrahedron Lett. 1988, 29, 5271.
2. Preliminary accounts of this work: Aoyama, Y.; Tanaka, Y.; Toi, H.; Ogoshi, H. J. Am. Chem. Soc. 1988, 110, 634.
3. (a) Helgeson, R. C.; Koga, K.; Timko, J. M.; Cram, D. J. J. Am. Chem. Soc. 1973, 95, 3021. (b) Rebek, J., Jr.; Askew, B.; Nemeth, D.; Parris, K. J. Am. Chem. Soc. 1987, 109, 2432. (c) Aoyama, Y.; Yamagishi, A.; Asagawa, M.; Toi, H.; Ogoshi, H. J. Am. Chem. Soc. 1988, 110, 4076 and references cited therein.
4. (a) Rebek, J., Jr.; Askew, B.; Ballester, P.; Buhr, C.; Jones, S.; Nemeth, D.; Williams, K. J. Am. Chem. Soc. 1987, 109, 5033. (b) Hamilton, A. D.; Van Engen, D. J. Am. Chem. Soc. 1987, 109, 5053. (c) Kelly, T. R.; Maguire, M. P. J. Am. Chem. Soc. 1987, 109, 6549. (d) Rebek, J., Jr.; Askew, B.; Ballester, P.; Buhr, C.; Costero, A.; Jones, S.; Williams, K. J. Am. Chem. Soc. 1987, 109, 6866. (e) Feibush, B.; Saha, M.; Onan, K.; Karger, B.; Giese, R. J. Am. Chem. Soc. 1987, 109, 7531. (f) Rebek, J., Jr.; Williams, K.; Parris, K.; Ballester, P.; Jeong, K.-S. Angew. Chem., Int. Ed. Engl. 1987, 26, 1244. (g) Chang, S.-K.; Hamilton, A. D. J. Am. Chem. Soc. 1988, 110, 1318. (h) Jeong, K. S.; Rebek, J., Jr. J. Am. Chem. Soc. 1988, 110, 3327. (i) Muehldorf, A. V.; Van Engen, D.; Warner, J. C.; Hamilton, A. D. J. Am. Chem. Soc. 1988, 110, 6561. (j) Lindsey, J. S.; Kearney, P. C.; Duff, R. J.; Tjivikua, P. T.; Rebek, J., Jr. J. Am. Chem. Soc. 1988, 110, 6575.
5. For examples of binding of organic hydroxyl compounds, see; (a) Moneta, W.; Baret, P.; Pierre, J.-L. J. Chem. Soc., Chem. Commun. 1985, 899. (b) Sheridan, R. E.; Whitlock, H. W., Jr. J. Am. Chem. Soc. 1986, 108, 7120. (c) Kobiro, K.; Takahashi, M,; Nishikawa, N.; Kakiuchi, K.; Tobe, Y.; Odaira, Y. Tetrahedron Lett. 1987, 28, 3825. (d) Sheridan, R. E.; Whitlock, H. W., Jr. J. Am. Chem. Soc. 1988, 110, 4071. For a review on the incorporation of various compounds including alcohols in crystal lattices of host compounds, see: Toda, F. Top. Curr. Chem. 1987, 140, 43. (6) (a) Erdtman, H.; Högberg, S.; Abrahamsson, S.; Nilsson, B. Tetrahedron Lett. 1968, 1679. (b) Högberg, A. G. S. J. Org. Chem. 1980, 45, 4498. (c) Högberg, A. G. S. J. Am. Chem. Soc. 1980, 102, 6046.
6. (a) Moran, J. R.; Karbach, S.; Cram, D. J. J. Am. Chem. Soc. 1982, 104, 5826, (b) Cram, D. J.; Stewart, K. D.; Goldberg, I.; Trueblood, K. N. J. Am. Chem. Soc. 1985, 107, 2574. (c) Cram, D. J.; Karbach, S.; Kim, Y. H.; Baczynskyj, L.; Kalleymeyn, G. W. J. Am. Chem. Soc. 1985, 107, 2575. (d) Cram, D. J.; Karbach, S.; Kim, H.-E.; Knobler, C. B.; Maverick, E. F.; Ericson, J. L.; Helgeson, R. C. J. Am. Chem. Soc. 1988, 110, 2229. (e) Cram, D. J.; Karbach, S.; Kim, Y. H.; Baczynskyj, L.; Marti, K.; Sampson, R. M.; Kalleymeyn, G. W. J. Am. Chem. Soc. 1988, 110, 2554.
7. (a) Schneider, H.-J.; Giittes, D.; Schneider, U. Angew. Chem., Int. Ed. Engl. 1986, 25, 647. (b) Schneider, H.-J.; Karmer, R.; Simova, S.; Schneider, U. J. Am. Chem. Soc, 1988, 110, 6442. (c) Schneider, H.-J.; Guttes, D.; Schneider, U. J. Am. Chem. Soc. 1988, 110, 6449.
8. Calixarenes are phenol—formaldehyde cyclocondensation oligomers: Gutsche, C. D.; Nam, K. C. J. Am. Chem. Soc. 1988, 110, 6153 and preceding papers in this series. For a review, see: Gutsche, C. D. Acc. Chem. Res. 1983, 16, 161.
9. 6 For X-ray structure, see: Nilsson, B. Acta Chem. Scand. 1968, 22, 732.
10. Dubois, M.; Gilles, K. A.; Hamilton, J. K.; Rebers, P. A.; Smith, F. Anal. Biochem. 1956, 28, 350.
11. Perlin, A. S.; Casu, B.; Koch, H. J. Can. J. Chem. 1970, 48, 2596.
12. Jones, A. J.; Grant, D. M.; Winkey, M. W.; Robins, R. K. J. Am. Chem. Soc. 1970, 92, 4078.
13. 6, see: Reuben, J. J. Am. Chem. Soc. 1984, 106, 6180.
14. (a) Hayward, L. D.; Angyal, S. J. Carbohydr. Res. 1977, 53, 13. (b) Carbohydrate; Collins, P. M., Ed.; Chapman and Hall: New York, 1987.
15. Johnson, C. E.; Bovey, F. A. J. Chem. Phys. 1958, 29, 1012.