Sugar-controlled aggregate formation in boronic acid-appended porphyrin amphiphiles

Journal of the American Chemical Society

Volumn 118, Issue 1, 1996, Pages 245-246

  Arimori, Susumu ^a   Takeuchi, Masayuki ^a   Shinkai, Seiji ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0346528311     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953323h     Document Type: Article

References (39)

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30. For saccharide recognition studies reported by other groups, see: Wulff. G.; Krieger, S.; Kubnewes, B.; Steisel, A. J. Am. Chem. Soc. 1994, 116, 409. Paugan, M.-F.; Smith, B. D. Tetrahedron Lett. 1993, 34, 3723. Mohler, L. K.; Czarnic, A. W J. Am. Chem. Soc. 1993, 115, 7037
31. For saccharide recognition studies reported by other groups, see: Wulff. G.; Krieger, S.; Kubnewes, B.; Steisel, A. J. Am. Chem. Soc. 1994, 116, 409. Paugan, M.-F.; Smith, B. D. Tetrahedron Lett. 1993, 34, 3723. Mohler, L. K.; Czarnic, A. W J. Am. Chem. Soc. 1993, 115, 7037
32. For saccharide recognition studies reported by other groups, see: Wulff. G.; Krieger, S.; Kubnewes, B.; Steisel, A. J. Am. Chem. Soc. 1994, 116, 409. Paugan, M.-F.; Smith, B. D. Tetrahedron Lett. 1993, 34, 3723. Mohler, L. K.; Czarnic, A. W J. Am. Chem. Soc. 1993, 115, 7037
33. 19a,b
34. Because of the similar solubility problem. we could not measure DSC and TEM in the absence of saccharides.
35. -3 M and [fructose] = 0.50 M in water - methanol, 15:1 v/v (pH 10.0 with 0.10 M carbonate buffer). The methanol concentration is higher than the standard concentration (i.e., water - methanol, 300:1 v/v) in order to carry out the measurement at the higher 2 concentration.
36. This propasal is consistent with recent NMR spectroscopic studies: Norrild, J. C.; Eggert, H J Am. Chem. Soc. 1995, 117, 1479 and references cited therein, James, T. D.; Sandanayake, K. R. A S.; Iguchi, R.; Shinkai, S. J. Am. Chem. Soc. 1995, 117, 8982.
37. This propasal is consistent with recent NMR spectroscopic studies: Norrild, J. C.; Eggert, H J Am. Chem. Soc. 1995, 117, 1479 and references cited therein, James, T. D.; Sandanayake, K. R. A S.; Iguchi, R.; Shinkai, S. J. Am. Chem. Soc. 1995, 117, 8982.
38. In Furhop's porphyrin system it took 3 months for 1 to grow as fibrous aggregates. In our system, 30 s sonication reproducibly resulted in the oriented aggregates.
39. Since the addition of uranyl acetate before sonicarion changes the solution pH and affects the boronic acid-monosaccharide complexation equilibrium, this method cannot be used. However, even though uranyl acetate was added after sonication, a shadowy string was observed in the center of a fibrous aggregate (see Figure 2). This suggests that the aggregates are tubular hollow fibers