Stereochemical effect of even-odd connecting links on supramolecular assemblies made of 1-glucosamide bolaamphiphiles

Journal of the American Chemical Society

Volumn 119, Issue 12, 1997, Pages 2812-2818

  Shimizu, Toshimi ^a   Masuda, Mitsutoshi ^a  

^a NATL INST OF MAT AND CHEM RES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE DERIVATIVE;

ARTICLE; CRYSTALLIZATION; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030929746     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961226y     Document Type: Article

References (42)

1. Fuhrhop, J.-H.; Helfrich, W. Chem. Rev. 1993, 93, 1565-1582.
2. For recent examples of molecular rods, see: (a) Pfannemueller, B.; Weite, W. Chem. Phys. Lipids 1985, 37, 227-240. (b) Yanagawa, H.; Ogawa, Y.; Furuta, H.; Tsuno, K. J. Am. Chem. Soc. 1989, 111, 4567-4570. (c) Itojima, Y.; Ogawa, Y.; Tsuno, K.; Handa, N.; Yanagawa, H. Biochemistry 1992, 31, 4757-4765. For molecular tubules, see: (d) Schnur, J. M. Science 1993, 262, 1669-1676. (e) Harada, A.; Li, J.; Kamachi, M. Nature 1993, 364, 516-518. (f) Thomas, B. N.; Safinya, C. R.; Plano, R. J.; Clark, N. A. Science 1995, 267, 1635-1638. (g) Kimizuka, N.; Kawasaki, T.; Hirata, K.; Kunitake, K. J. Am. Chem. Soc. 1995, 117, 6360-6361. (h) Hartgerink, J. D.; Granja, J. R.; Milligan, R. A.; Ghadiri, M. R. J. Am. Chem. Soc. 1996, 118, 43-50. (i) Shimizu, T.; Kogiso, M.; Masuda, M. Nature 1996, 383, 487-488. For molecular scrolls, see: (J) Fuhrhop, J.-H.; Demoulin, C.; Rosenberg, J.; Boettcher, C. J. Am. Chem. Soc. 1990, 112, 2827-2829. For molecular ribbons, see: (k) Shimizu, T.; Mori, M.; Minamikawa, H.; Hato, M. J. Chem. Soc., Chem. Commun. 1990, 183-185. (l) Imae, T.; Takahashi, Y.; Muramatsu, H. J. Am. Chem. Soc. 1992, 114, 3414-3419. (m) Shimizu, T.; Hato, M. Biochim. Biophys. Acta 1993, 1147, 50-58. (n) Frankel, D. A.; O'Brien, D. F. J. Am. Chem. Soc. 1994, 116, 10057-10069. (o) Endisch, C.; Bottcher, C.; Fuhrhop, J.-H. J. Am. Chem. Soc. 1995, 117, 8273-8274.
3. For recent examples of molecular rods, see: (a) Pfannemueller, B.; Weite, W. Chem. Phys. Lipids 1985, 37, 227-240. (b) Yanagawa, H.; Ogawa, Y.; Furuta, H.; Tsuno, K. J. Am. Chem. Soc. 1989, 111, 4567-4570. (c) Itojima, Y.; Ogawa, Y.; Tsuno, K.; Handa, N.; Yanagawa, H. Biochemistry 1992, 31, 4757-4765. For molecular tubules, see: (d) Schnur, J. M. Science 1993, 262, 1669-1676. (e) Harada, A.; Li, J.; Kamachi, M. Nature 1993, 364, 516-518. (f) Thomas, B. N.; Safinya, C. R.; Plano, R. J.; Clark, N. A. Science 1995, 267, 1635-1638. (g) Kimizuka, N.; Kawasaki, T.; Hirata, K.; Kunitake, K. J. Am. Chem. Soc. 1995, 117, 6360-6361. (h) Hartgerink, J. D.; Granja, J. R.; Milligan, R. A.; Ghadiri, M. R. J. Am. Chem. Soc. 1996, 118, 43-50. (i) Shimizu, T.; Kogiso, M.; Masuda, M. Nature 1996, 383, 487-488. For molecular scrolls, see: (J) Fuhrhop, J.-H.; Demoulin, C.; Rosenberg, J.; Boettcher, C. J. Am. Chem. Soc. 1990, 112, 2827-2829. For molecular ribbons, see: (k) Shimizu, T.; Mori, M.; Minamikawa, H.; Hato, M. J. Chem. Soc., Chem. Commun. 1990, 183-185. (l) Imae, T.; Takahashi, Y.; Muramatsu, H. J. Am. Chem. Soc. 1992, 114, 3414-3419. (m) Shimizu, T.; Hato, M. Biochim. Biophys. Acta 1993, 1147, 50-58. (n) Frankel, D. A.; O'Brien, D. F. J. Am. Chem. Soc. 1994, 116, 10057-10069. (o) Endisch, C.; Bottcher, C.; Fuhrhop, J.-H. J. Am. Chem. Soc. 1995, 117, 8273-8274.
4. For recent examples of molecular rods, see: (a) Pfannemueller, B.; Weite, W. Chem. Phys. Lipids 1985, 37, 227-240. (b) Yanagawa, H.; Ogawa, Y.; Furuta, H.; Tsuno, K. J. Am. Chem. Soc. 1989, 111, 4567-4570. (c) Itojima, Y.; Ogawa, Y.; Tsuno, K.; Handa, N.; Yanagawa, H. Biochemistry 1992, 31, 4757-4765. For molecular tubules, see: (d) Schnur, J. M. Science 1993, 262, 1669-1676. (e) Harada, A.; Li, J.; Kamachi, M. Nature 1993, 364, 516-518. (f) Thomas, B. N.; Safinya, C. R.; Plano, R. J.; Clark, N. A. Science 1995, 267, 1635-1638. (g) Kimizuka, N.; Kawasaki, T.; Hirata, K.; Kunitake, K. J. Am. Chem. Soc. 1995, 117, 6360-6361. (h) Hartgerink, J. D.; Granja, J. R.; Milligan, R. A.; Ghadiri, M. R. J. Am. Chem. Soc. 1996, 118, 43-50. (i) Shimizu, T.; Kogiso, M.; Masuda, M. Nature 1996, 383, 487-488. For molecular scrolls, see: (J) Fuhrhop, J.-H.; Demoulin, C.; Rosenberg, J.; Boettcher, C. J. Am. Chem. Soc. 1990, 112, 2827-2829. For molecular ribbons, see: (k) Shimizu, T.; Mori, M.; Minamikawa, H.; Hato, M. J. Chem. Soc., Chem. Commun. 1990, 183-185. (l) Imae, T.; Takahashi, Y.; Muramatsu, H. J. Am. Chem. Soc. 1992, 114, 3414-3419. (m) Shimizu, T.; Hato, M. Biochim. Biophys. Acta 1993, 1147, 50-58. (n) Frankel, D. A.; O'Brien, D. F. J. Am. Chem. Soc. 1994, 116, 10057-10069. (o) Endisch, C.; Bottcher, C.; Fuhrhop, J.-H. J. Am. Chem. Soc. 1995, 117, 8273-8274.
5. For recent examples of molecular rods, see: (a) Pfannemueller, B.; Weite, W. Chem. Phys. Lipids 1985, 37, 227-240. (b) Yanagawa, H.; Ogawa, Y.; Furuta, H.; Tsuno, K. J. Am. Chem. Soc. 1989, 111, 4567-4570. (c) Itojima, Y.; Ogawa, Y.; Tsuno, K.; Handa, N.; Yanagawa, H. Biochemistry 1992, 31, 4757-4765. For molecular tubules, see: (d) Schnur, J. M. Science 1993, 262, 1669-1676. (e) Harada, A.; Li, J.; Kamachi, M. Nature 1993, 364, 516-518. (f) Thomas, B. N.; Safinya, C. R.; Plano, R. J.; Clark, N. A. Science 1995, 267, 1635-1638. (g) Kimizuka, N.; Kawasaki, T.; Hirata, K.; Kunitake, K. J. Am. Chem. Soc. 1995, 117, 6360-6361. (h) Hartgerink, J. D.; Granja, J. R.; Milligan, R. A.; Ghadiri, M. R. J. Am. Chem. Soc. 1996, 118, 43-50. (i) Shimizu, T.; Kogiso, M.; Masuda, M. Nature 1996, 383, 487-488. For molecular scrolls, see: (J) Fuhrhop, J.-H.; Demoulin, C.; Rosenberg, J.; Boettcher, C. J. Am. Chem. Soc. 1990, 112, 2827-2829. For molecular ribbons, see: (k) Shimizu, T.; Mori, M.; Minamikawa, H.; Hato, M. J. Chem. Soc., Chem. Commun. 1990, 183-185. (l) Imae, T.; Takahashi, Y.; Muramatsu, H. J. Am. Chem. Soc. 1992, 114, 3414-3419. (m) Shimizu, T.; Hato, M. Biochim. Biophys. Acta 1993, 1147, 50-58. (n) Frankel, D. A.; O'Brien, D. F. J. Am. Chem. Soc. 1994, 116, 10057-10069. (o) Endisch, C.; Bottcher, C.; Fuhrhop, J.-H. J. Am. Chem. Soc. 1995, 117, 8273-8274.
6. For recent examples of molecular rods, see: (a) Pfannemueller, B.; Weite, W. Chem. Phys. Lipids 1985, 37, 227-240. (b) Yanagawa, H.; Ogawa, Y.; Furuta, H.; Tsuno, K. J. Am. Chem. Soc. 1989, 111, 4567-4570. (c) Itojima, Y.; Ogawa, Y.; Tsuno, K.; Handa, N.; Yanagawa, H. Biochemistry 1992, 31, 4757-4765. For molecular tubules, see: (d) Schnur, J. M. Science 1993, 262, 1669-1676. (e) Harada, A.; Li, J.; Kamachi, M. Nature 1993, 364, 516-518. (f) Thomas, B. N.; Safinya, C. R.; Plano, R. J.; Clark, N. A. Science 1995, 267, 1635-1638. (g) Kimizuka, N.; Kawasaki, T.; Hirata, K.; Kunitake, K. J. Am. Chem. Soc. 1995, 117, 6360-6361. (h) Hartgerink, J. D.; Granja, J. R.; Milligan, R. A.; Ghadiri, M. R. J. Am. Chem. Soc. 1996, 118, 43-50. (i) Shimizu, T.; Kogiso, M.; Masuda, M. Nature 1996, 383, 487-488. For molecular scrolls, see: (J) Fuhrhop, J.-H.; Demoulin, C.; Rosenberg, J.; Boettcher, C. J. Am. Chem. Soc. 1990, 112, 2827-2829. For molecular ribbons, see: (k) Shimizu, T.; Mori, M.; Minamikawa, H.; Hato, M. J. Chem. Soc., Chem. Commun. 1990, 183-185. (l) Imae, T.; Takahashi, Y.; Muramatsu, H. J. Am. Chem. Soc. 1992, 114, 3414-3419. (m) Shimizu, T.; Hato, M. Biochim. Biophys. Acta 1993, 1147, 50-58. (n) Frankel, D. A.; O'Brien, D. F. J. Am. Chem. Soc. 1994, 116, 10057-10069. (o) Endisch, C.; Bottcher, C.; Fuhrhop, J.-H. J. Am. Chem. Soc. 1995, 117, 8273-8274.
7. For recent examples of molecular rods, see: (a) Pfannemueller, B.; Weite, W. Chem. Phys. Lipids 1985, 37, 227-240. (b) Yanagawa, H.; Ogawa, Y.; Furuta, H.; Tsuno, K. J. Am. Chem. Soc. 1989, 111, 4567-4570. (c) Itojima, Y.; Ogawa, Y.; Tsuno, K.; Handa, N.; Yanagawa, H. Biochemistry 1992, 31, 4757-4765. For molecular tubules, see: (d) Schnur, J. M. Science 1993, 262, 1669-1676. (e) Harada, A.; Li, J.; Kamachi, M. Nature 1993, 364, 516-518. (f) Thomas, B. N.; Safinya, C. R.; Plano, R. J.; Clark, N. A. Science 1995, 267, 1635-1638. (g) Kimizuka, N.; Kawasaki, T.; Hirata, K.; Kunitake, K. J. Am. Chem. Soc. 1995, 117, 6360-6361. (h) Hartgerink, J. D.; Granja, J. R.; Milligan, R. A.; Ghadiri, M. R. J. Am. Chem. Soc. 1996, 118, 43-50. (i) Shimizu, T.; Kogiso, M.; Masuda, M. Nature 1996, 383, 487-488. For molecular scrolls, see: (J) Fuhrhop, J.-H.; Demoulin, C.; Rosenberg, J.; Boettcher, C. J. Am. Chem. Soc. 1990, 112, 2827-2829. For molecular ribbons, see: (k) Shimizu, T.; Mori, M.; Minamikawa, H.; Hato, M. J. Chem. Soc., Chem. Commun. 1990, 183-185. (l) Imae, T.; Takahashi, Y.; Muramatsu, H. J. Am. Chem. Soc. 1992, 114, 3414-3419. (m) Shimizu, T.; Hato, M. Biochim. Biophys. Acta 1993, 1147, 50-58. (n) Frankel, D. A.; O'Brien, D. F. J. Am. Chem. Soc. 1994, 116, 10057-10069. (o) Endisch, C.; Bottcher, C.; Fuhrhop, J.-H. J. Am. Chem. Soc. 1995, 117, 8273-8274.
8. For recent examples of molecular rods, see: (a) Pfannemueller, B.; Weite, W. Chem. Phys. Lipids 1985, 37, 227-240. (b) Yanagawa, H.; Ogawa, Y.; Furuta, H.; Tsuno, K. J. Am. Chem. Soc. 1989, 111, 4567-4570. (c) Itojima, Y.; Ogawa, Y.; Tsuno, K.; Handa, N.; Yanagawa, H. Biochemistry 1992, 31, 4757-4765. For molecular tubules, see: (d) Schnur, J. M. Science 1993, 262, 1669-1676. (e) Harada, A.; Li, J.; Kamachi, M. Nature 1993, 364, 516-518. (f) Thomas, B. N.; Safinya, C. R.; Plano, R. J.; Clark, N. A. Science 1995, 267, 1635-1638. (g) Kimizuka, N.; Kawasaki, T.; Hirata, K.; Kunitake, K. J. Am. Chem. Soc. 1995, 117, 6360-6361. (h) Hartgerink, J. D.; Granja, J. R.; Milligan, R. A.; Ghadiri, M. R. J. Am. Chem. Soc. 1996, 118, 43-50. (i) Shimizu, T.; Kogiso, M.; Masuda, M. Nature 1996, 383, 487-488. For molecular scrolls, see: (J) Fuhrhop, J.-H.; Demoulin, C.; Rosenberg, J.; Boettcher, C. J. Am. Chem. Soc. 1990, 112, 2827-2829. For molecular ribbons, see: (k) Shimizu, T.; Mori, M.; Minamikawa, H.; Hato, M. J. Chem. Soc., Chem. Commun. 1990, 183-185. (l) Imae, T.; Takahashi, Y.; Muramatsu, H. J. Am. Chem. Soc. 1992, 114, 3414-3419. (m) Shimizu, T.; Hato, M. Biochim. Biophys. Acta 1993, 1147, 50-58. (n) Frankel, D. A.; O'Brien, D. F. J. Am. Chem. Soc. 1994, 116, 10057-10069. (o) Endisch, C.; Bottcher, C.; Fuhrhop, J.-H. J. Am. Chem. Soc. 1995, 117, 8273-8274.
9. For recent examples of molecular rods, see: (a) Pfannemueller, B.; Weite, W. Chem. Phys. Lipids 1985, 37, 227-240. (b) Yanagawa, H.; Ogawa, Y.; Furuta, H.; Tsuno, K. J. Am. Chem. Soc. 1989, 111, 4567-4570. (c) Itojima, Y.; Ogawa, Y.; Tsuno, K.; Handa, N.; Yanagawa, H. Biochemistry 1992, 31, 4757-4765. For molecular tubules, see: (d) Schnur, J. M. Science 1993, 262, 1669-1676. (e) Harada, A.; Li, J.; Kamachi, M. Nature 1993, 364, 516-518. (f) Thomas, B. N.; Safinya, C. R.; Plano, R. J.; Clark, N. A. Science 1995, 267, 1635-1638. (g) Kimizuka, N.; Kawasaki, T.; Hirata, K.; Kunitake, K. J. Am. Chem. Soc. 1995, 117, 6360-6361. (h) Hartgerink, J. D.; Granja, J. R.; Milligan, R. A.; Ghadiri, M. R. J. Am. Chem. Soc. 1996, 118, 43-50. (i) Shimizu, T.; Kogiso, M.; Masuda, M. Nature 1996, 383, 487-488. For molecular scrolls, see: (J) Fuhrhop, J.-H.; Demoulin, C.; Rosenberg, J.; Boettcher, C. J. Am. Chem. Soc. 1990, 112, 2827-2829. For molecular ribbons, see: (k) Shimizu, T.; Mori, M.; Minamikawa, H.; Hato, M. J. Chem. Soc., Chem. Commun. 1990, 183-185. (l) Imae, T.; Takahashi, Y.; Muramatsu, H. J. Am. Chem. Soc. 1992, 114, 3414-3419. (m) Shimizu, T.; Hato, M. Biochim. Biophys. Acta 1993, 1147, 50-58. (n) Frankel, D. A.; O'Brien, D. F. J. Am. Chem. Soc. 1994, 116, 10057-10069. (o) Endisch, C.; Bottcher, C.; Fuhrhop, J.-H. J. Am. Chem. Soc. 1995, 117, 8273-8274.
10. For recent examples of molecular rods, see: (a) Pfannemueller, B.; Weite, W. Chem. Phys. Lipids 1985, 37, 227-240. (b) Yanagawa, H.; Ogawa, Y.; Furuta, H.; Tsuno, K. J. Am. Chem. Soc. 1989, 111, 4567-4570. (c) Itojima, Y.; Ogawa, Y.; Tsuno, K.; Handa, N.; Yanagawa, H. Biochemistry 1992, 31, 4757-4765. For molecular tubules, see: (d) Schnur, J. M. Science 1993, 262, 1669-1676. (e) Harada, A.; Li, J.; Kamachi, M. Nature 1993, 364, 516-518. (f) Thomas, B. N.; Safinya, C. R.; Plano, R. J.; Clark, N. A. Science 1995, 267, 1635-1638. (g) Kimizuka, N.; Kawasaki, T.; Hirata, K.; Kunitake, K. J. Am. Chem. Soc. 1995, 117, 6360-6361. (h) Hartgerink, J. D.; Granja, J. R.; Milligan, R. A.; Ghadiri, M. R. J. Am. Chem. Soc. 1996, 118, 43-50. (i) Shimizu, T.; Kogiso, M.; Masuda, M. Nature 1996, 383, 487-488. For molecular scrolls, see: (J) Fuhrhop, J.-H.; Demoulin, C.; Rosenberg, J.; Boettcher, C. J. Am. Chem. Soc. 1990, 112, 2827-2829. For molecular ribbons, see: (k) Shimizu, T.; Mori, M.; Minamikawa, H.; Hato, M. J. Chem. Soc., Chem. Commun. 1990, 183-185. (l) Imae, T.; Takahashi, Y.; Muramatsu, H. J. Am. Chem. Soc. 1992, 114, 3414-3419. (m) Shimizu, T.; Hato, M. Biochim. Biophys. Acta 1993, 1147, 50-58. (n) Frankel, D. A.; O'Brien, D. F. J. Am. Chem. Soc. 1994, 116, 10057-10069. (o) Endisch, C.; Bottcher, C.; Fuhrhop, J.-H. J. Am. Chem. Soc. 1995, 117, 8273-8274.
11. For recent examples of molecular rods, see: (a) Pfannemueller, B.; Weite, W. Chem. Phys. Lipids 1985, 37, 227-240. (b) Yanagawa, H.; Ogawa, Y.; Furuta, H.; Tsuno, K. J. Am. Chem. Soc. 1989, 111, 4567-4570. (c) Itojima, Y.; Ogawa, Y.; Tsuno, K.; Handa, N.; Yanagawa, H. Biochemistry 1992, 31, 4757-4765. For molecular tubules, see: (d) Schnur, J. M. Science 1993, 262, 1669-1676. (e) Harada, A.; Li, J.; Kamachi, M. Nature 1993, 364, 516-518. (f) Thomas, B. N.; Safinya, C. R.; Plano, R. J.; Clark, N. A. Science 1995, 267, 1635-1638. (g) Kimizuka, N.; Kawasaki, T.; Hirata, K.; Kunitake, K. J. Am. Chem. Soc. 1995, 117, 6360-6361. (h) Hartgerink, J. D.; Granja, J. R.; Milligan, R. A.; Ghadiri, M. R. J. Am. Chem. Soc. 1996, 118, 43-50. (i) Shimizu, T.; Kogiso, M.; Masuda, M. Nature 1996, 383, 487-488. For molecular scrolls, see: (J) Fuhrhop, J.-H.; Demoulin, C.; Rosenberg, J.; Boettcher, C. J. Am. Chem. Soc. 1990, 112, 2827-2829. For molecular ribbons, see: (k) Shimizu, T.; Mori, M.; Minamikawa, H.; Hato, M. J. Chem. Soc., Chem. Commun. 1990, 183-185. (l) Imae, T.; Takahashi, Y.; Muramatsu, H. J. Am. Chem. Soc. 1992, 114, 3414-3419. (m) Shimizu, T.; Hato, M. Biochim. Biophys. Acta 1993, 1147, 50-58. (n) Frankel, D. A.; O'Brien, D. F. J. Am. Chem. Soc. 1994, 116, 10057-10069. (o) Endisch, C.; Bottcher, C.; Fuhrhop, J.-H. J. Am. Chem. Soc. 1995, 117, 8273-8274.
12. For recent examples of molecular rods, see: (a) Pfannemueller, B.; Weite, W. Chem. Phys. Lipids 1985, 37, 227-240. (b) Yanagawa, H.; Ogawa, Y.; Furuta, H.; Tsuno, K. J. Am. Chem. Soc. 1989, 111, 4567-4570. (c) Itojima, Y.; Ogawa, Y.; Tsuno, K.; Handa, N.; Yanagawa, H. Biochemistry 1992, 31, 4757-4765. For molecular tubules, see: (d) Schnur, J. M. Science 1993, 262, 1669-1676. (e) Harada, A.; Li, J.; Kamachi, M. Nature 1993, 364, 516-518. (f) Thomas, B. N.; Safinya, C. R.; Plano, R. J.; Clark, N. A. Science 1995, 267, 1635-1638. (g) Kimizuka, N.; Kawasaki, T.; Hirata, K.; Kunitake, K. J. Am. Chem. Soc. 1995, 117, 6360-6361. (h) Hartgerink, J. D.; Granja, J. R.; Milligan, R. A.; Ghadiri, M. R. J. Am. Chem. Soc. 1996, 118, 43-50. (i) Shimizu, T.; Kogiso, M.; Masuda, M. Nature 1996, 383, 487-488. For molecular scrolls, see: (J) Fuhrhop, J.-H.; Demoulin, C.; Rosenberg, J.; Boettcher, C. J. Am. Chem. Soc. 1990, 112, 2827-2829. For molecular ribbons, see: (k) Shimizu, T.; Mori, M.; Minamikawa, H.; Hato, M. J. Chem. Soc., Chem. Commun. 1990, 183-185. (l) Imae, T.; Takahashi, Y.; Muramatsu, H. J. Am. Chem. Soc. 1992, 114, 3414-3419. (m) Shimizu, T.; Hato, M. Biochim. Biophys. Acta 1993, 1147, 50-58. (n) Frankel, D. A.; O'Brien, D. F. J. Am. Chem. Soc. 1994, 116, 10057-10069. (o) Endisch, C.; Bottcher, C.; Fuhrhop, J.-H. J. Am. Chem. Soc. 1995, 117, 8273-8274.
13. For recent examples of molecular rods, see: (a) Pfannemueller, B.; Weite, W. Chem. Phys. Lipids 1985, 37, 227-240. (b) Yanagawa, H.; Ogawa, Y.; Furuta, H.; Tsuno, K. J. Am. Chem. Soc. 1989, 111, 4567-4570. (c) Itojima, Y.; Ogawa, Y.; Tsuno, K.; Handa, N.; Yanagawa, H. Biochemistry 1992, 31, 4757-4765. For molecular tubules, see: (d) Schnur, J. M. Science 1993, 262, 1669-1676. (e) Harada, A.; Li, J.; Kamachi, M. Nature 1993, 364, 516-518. (f) Thomas, B. N.; Safinya, C. R.; Plano, R. J.; Clark, N. A. Science 1995, 267, 1635-1638. (g) Kimizuka, N.; Kawasaki, T.; Hirata, K.; Kunitake, K. J. Am. Chem. Soc. 1995, 117, 6360-6361. (h) Hartgerink, J. D.; Granja, J. R.; Milligan, R. A.; Ghadiri, M. R. J. Am. Chem. Soc. 1996, 118, 43-50. (i) Shimizu, T.; Kogiso, M.; Masuda, M. Nature 1996, 383, 487-488. For molecular scrolls, see: (J) Fuhrhop, J.-H.; Demoulin, C.; Rosenberg, J.; Boettcher, C. J. Am. Chem. Soc. 1990, 112, 2827-2829. For molecular ribbons, see: (k) Shimizu, T.; Mori, M.; Minamikawa, H.; Hato, M. J. Chem. Soc., Chem. Commun. 1990, 183-185. (l) Imae, T.; Takahashi, Y.; Muramatsu, H. J. Am. Chem. Soc. 1992, 114, 3414-3419. (m) Shimizu, T.; Hato, M. Biochim. Biophys. Acta 1993, 1147, 50-58. (n) Frankel, D. A.; O'Brien, D. F. J. Am. Chem. Soc. 1994, 116, 10057-10069. (o) Endisch, C.; Bottcher, C.; Fuhrhop, J.-H. J. Am. Chem. Soc. 1995, 117, 8273-8274.
14. For recent examples of molecular rods, see: (a) Pfannemueller, B.; Weite, W. Chem. Phys. Lipids 1985, 37, 227-240. (b) Yanagawa, H.; Ogawa, Y.; Furuta, H.; Tsuno, K. J. Am. Chem. Soc. 1989, 111, 4567-4570. (c) Itojima, Y.; Ogawa, Y.; Tsuno, K.; Handa, N.; Yanagawa, H. Biochemistry 1992, 31, 4757-4765. For molecular tubules, see: (d) Schnur, J. M. Science 1993, 262, 1669-1676. (e) Harada, A.; Li, J.; Kamachi, M. Nature 1993, 364, 516-518. (f) Thomas, B. N.; Safinya, C. R.; Plano, R. J.; Clark, N. A. Science 1995, 267, 1635-1638. (g) Kimizuka, N.; Kawasaki, T.; Hirata, K.; Kunitake, K. J. Am. Chem. Soc. 1995, 117, 6360-6361. (h) Hartgerink, J. D.; Granja, J. R.; Milligan, R. A.; Ghadiri, M. R. J. Am. Chem. Soc. 1996, 118, 43-50. (i) Shimizu, T.; Kogiso, M.; Masuda, M. Nature 1996, 383, 487-488. For molecular scrolls, see: (J) Fuhrhop, J.-H.; Demoulin, C.; Rosenberg, J.; Boettcher, C. J. Am. Chem. Soc. 1990, 112, 2827-2829. For molecular ribbons, see: (k) Shimizu, T.; Mori, M.; Minamikawa, H.; Hato, M. J. Chem. Soc., Chem. Commun. 1990, 183-185. (l) Imae, T.; Takahashi, Y.; Muramatsu, H. J. Am. Chem. Soc. 1992, 114, 3414-3419. (m) Shimizu, T.; Hato, M. Biochim. Biophys. Acta 1993, 1147, 50-58. (n) Frankel, D. A.; O'Brien, D. F. J. Am. Chem. Soc. 1994, 116, 10057-10069. (o) Endisch, C.; Bottcher, C.; Fuhrhop, J.-H. J. Am. Chem. Soc. 1995, 117, 8273-8274.
15. For recent examples of molecular rods, see: (a) Pfannemueller, B.; Weite, W. Chem. Phys. Lipids 1985, 37, 227-240. (b) Yanagawa, H.; Ogawa, Y.; Furuta, H.; Tsuno, K. J. Am. Chem. Soc. 1989, 111, 4567-4570. (c) Itojima, Y.; Ogawa, Y.; Tsuno, K.; Handa, N.; Yanagawa, H. Biochemistry 1992, 31, 4757-4765. For molecular tubules, see: (d) Schnur, J. M. Science 1993, 262, 1669-1676. (e) Harada, A.; Li, J.; Kamachi, M. Nature 1993, 364, 516-518. (f) Thomas, B. N.; Safinya, C. R.; Plano, R. J.; Clark, N. A. Science 1995, 267, 1635-1638. (g) Kimizuka, N.; Kawasaki, T.; Hirata, K.; Kunitake, K. J. Am. Chem. Soc. 1995, 117, 6360-6361. (h) Hartgerink, J. D.; Granja, J. R.; Milligan, R. A.; Ghadiri, M. R. J. Am. Chem. Soc. 1996, 118, 43-50. (i) Shimizu, T.; Kogiso, M.; Masuda, M. Nature 1996, 383, 487-488. For molecular scrolls, see: (J) Fuhrhop, J.-H.; Demoulin, C.; Rosenberg, J.; Boettcher, C. J. Am. Chem. Soc. 1990, 112, 2827-2829. For molecular ribbons, see: (k) Shimizu, T.; Mori, M.; Minamikawa, H.; Hato, M. J. Chem. Soc., Chem. Commun. 1990, 183-185. (l) Imae, T.; Takahashi, Y.; Muramatsu, H. J. Am. Chem. Soc. 1992, 114, 3414-3419. (m) Shimizu, T.; Hato, M. Biochim. Biophys. Acta 1993, 1147, 50-58. (n) Frankel, D. A.; O'Brien, D. F. J. Am. Chem. Soc. 1994, 116, 10057-10069. (o) Endisch, C.; Bottcher, C.; Fuhrhop, J.-H. J. Am. Chem. Soc. 1995, 117, 8273-8274.
16. For recent examples of molecular rods, see: (a) Pfannemueller, B.; Weite, W. Chem. Phys. Lipids 1985, 37, 227-240. (b) Yanagawa, H.; Ogawa, Y.; Furuta, H.; Tsuno, K. J. Am. Chem. Soc. 1989, 111, 4567-4570. (c) Itojima, Y.; Ogawa, Y.; Tsuno, K.; Handa, N.; Yanagawa, H. Biochemistry 1992, 31, 4757-4765. For molecular tubules, see: (d) Schnur, J. M. Science 1993, 262, 1669-1676. (e) Harada, A.; Li, J.; Kamachi, M. Nature 1993, 364, 516-518. (f) Thomas, B. N.; Safinya, C. R.; Plano, R. J.; Clark, N. A. Science 1995, 267, 1635-1638. (g) Kimizuka, N.; Kawasaki, T.; Hirata, K.; Kunitake, K. J. Am. Chem. Soc. 1995, 117, 6360-6361. (h) Hartgerink, J. D.; Granja, J. R.; Milligan, R. A.; Ghadiri, M. R. J. Am. Chem. Soc. 1996, 118, 43-50. (i) Shimizu, T.; Kogiso, M.; Masuda, M. Nature 1996, 383, 487-488. For molecular scrolls, see: (J) Fuhrhop, J.-H.; Demoulin, C.; Rosenberg, J.; Boettcher, C. J. Am. Chem. Soc. 1990, 112, 2827-2829. For molecular ribbons, see: (k) Shimizu, T.; Mori, M.; Minamikawa, H.; Hato, M. J. Chem. Soc., Chem. Commun. 1990, 183-185. (l) Imae, T.; Takahashi, Y.; Muramatsu, H. J. Am. Chem. Soc. 1992, 114, 3414-3419. (m) Shimizu, T.; Hato, M. Biochim. Biophys. Acta 1993, 1147, 50-58. (n) Frankel, D. A.; O'Brien, D. F. J. Am. Chem. Soc. 1994, 116, 10057-10069. (o) Endisch, C.; Bottcher, C.; Fuhrhop, J.-H. J. Am. Chem. Soc. 1995, 117, 8273-8274.
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