Unconventional Amphiphilic Polymers Based on Chiral Polyethylene Oxides

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 1-2, 1997, Pages 122-125

  Janssen, Henk M ^a   Peeters, Emiel ^a   Van Zundert, Marga F ^a   Van Genderen, Marcel H P ^a   Meijer, E W ^a  

^a EINDHOVEN UNIVERSITY OF TECHNOLOGY   (Netherlands)

Author keywords

Amphiphiles; Chirality; Crown ethers; Helical structures; Polymers

Indexed keywords

EID: 0030788429     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199701221     Document Type: Article

References (58)

1. P. B. Hurbury, T. Zhang, P. S. Kim, T. Alber, Science, 1993. 262, 1401; A. M. Gronenborn, G. M. Clore, Ibid. 1994, 263, 536; C. Cohen, D. A. D. Parry, ibid. 1994, 263, 488; P. Lavigne, F. D. Sönnichsen, C. M. Kay, R. S. Hodges, K. J. Lumb, P. S. Kim, Ibid. 1996, 271, 1136; W.M. Kazmierski, J. McDermed, A. Aulabaugh, Chem. Eur. J. 1996, 2, 403.
2. P. B. Hurbury, T. Zhang, P. S. Kim, T. Alber, Science, 1993. 262, 1401; A. M. Gronenborn, G. M. Clore, Ibid. 1994, 263, 536; C. Cohen, D. A. D. Parry, ibid. 1994, 263, 488; P. Lavigne, F. D. Sönnichsen, C. M. Kay, R. S. Hodges, K. J. Lumb, P. S. Kim, Ibid. 1996, 271, 1136; W.M. Kazmierski, J. McDermed, A. Aulabaugh, Chem. Eur. J. 1996, 2, 403.
3. P. B. Hurbury, T. Zhang, P. S. Kim, T. Alber, Science, 1993. 262, 1401; A. M. Gronenborn, G. M. Clore, Ibid. 1994, 263, 536; C. Cohen, D. A. D. Parry, ibid. 1994, 263, 488; P. Lavigne, F. D. Sönnichsen, C. M. Kay, R. S. Hodges, K. J. Lumb, P. S. Kim, Ibid. 1996, 271, 1136; W.M. Kazmierski, J. McDermed, A. Aulabaugh, Chem. Eur. J. 1996, 2, 403.
4. P. B. Hurbury, T. Zhang, P. S. Kim, T. Alber, Science, 1993. 262, 1401; A. M. Gronenborn, G. M. Clore, Ibid. 1994, 263, 536; C. Cohen, D. A. D. Parry, ibid. 1994, 263, 488; P. Lavigne, F. D. Sönnichsen, C. M. Kay, R. S. Hodges, K. J. Lumb, P. S. Kim, Ibid. 1996, 271, 1136; W.M. Kazmierski, J. McDermed, A. Aulabaugh, Chem. Eur. J. 1996, 2, 403.
5. P. B. Hurbury, T. Zhang, P. S. Kim, T. Alber, Science, 1993. 262, 1401; A. M. Gronenborn, G. M. Clore, Ibid. 1994, 263, 536; C. Cohen, D. A. D. Parry, ibid. 1994, 263, 488; P. Lavigne, F. D. Sönnichsen, C. M. Kay, R. S. Hodges, K. J. Lumb, P. S. Kim, Ibid. 1996, 271, 1136; W.M. Kazmierski, J. McDermed, A. Aulabaugh, Chem. Eur. J. 1996, 2, 403.
6. R. S. Hodges, J. Sodek, L. B. Smillie, L. Jurasek, Cold Spring Harbor Symp. Quant. Biol. 1972, 37, 299; E. K. O'Shea, R. Rutkowski, W. F. Statford III. P. S. Kim, Science 1989, 245, 646; E. K. O'Shea, J. D. Klemm, P. S. Kim, T. Alber, ibid, 1991, 254, 539; F. K. Junius, A. S. Weiss, G. F. King, Eur. J. Biochew. 1993, 214, 415.
7. R. S. Hodges, J. Sodek, L. B. Smillie, L. Jurasek, Cold Spring Harbor Symp. Quant. Biol. 1972, 37, 299; E. K. O'Shea, R. Rutkowski, W. F. Statford III. P. S. Kim, Science 1989, 245, 646; E. K. O'Shea, J. D. Klemm, P. S. Kim, T. Alber, ibid, 1991, 254, 539; F. K. Junius, A. S. Weiss, G. F. King, Eur. J. Biochew. 1993, 214, 415.
8. R. S. Hodges, J. Sodek, L. B. Smillie, L. Jurasek, Cold Spring Harbor Symp. Quant. Biol. 1972, 37, 299; E. K. O'Shea, R. Rutkowski, W. F. Statford III. P. S. Kim, Science 1989, 245, 646; E. K. O'Shea, J. D. Klemm, P. S. Kim, T. Alber, ibid, 1991, 254, 539; F. K. Junius, A. S. Weiss, G. F. King, Eur. J. Biochew. 1993, 214, 415.
9. R. S. Hodges, J. Sodek, L. B. Smillie, L. Jurasek, Cold Spring Harbor Symp. Quant. Biol. 1972, 37, 299; E. K. O'Shea, R. Rutkowski, W. F. Statford III. P. S. Kim, Science 1989, 245, 646; E. K. O'Shea, J. D. Klemm, P. S. Kim, T. Alber, ibid, 1991, 254, 539; F. K. Junius, A. S. Weiss, G. F. King, Eur. J. Biochew. 1993, 214, 415.
10. K. T. O'Neill, R. H. Hoess, W. F. DeGrado, Science 1990, 249, 774; N. E. Zhou, C. M. Kay, R. S. Hodges, Biochemistry 1992, 31, 5739; T. J. Graddis, D. G. Myszka, I. M. Chaiken, ibid. 1993, 32, 12644.
11. K. T. O'Neill, R. H. Hoess, W. F. DeGrado, Science 1990, 249, 774; N. E. Zhou, C. M. Kay, R. S. Hodges, Biochemistry 1992, 31, 5739; T. J. Graddis, D. G. Myszka, I. M. Chaiken, ibid. 1993, 32, 12644.
12. K. T. O'Neill, R. H. Hoess, W. F. DeGrado, Science 1990, 249, 774; N. E. Zhou, C. M. Kay, R. S. Hodges, Biochemistry 1992, 31, 5739; T. J. Graddis, D. G. Myszka, I. M. Chaiken, ibid. 1993, 32, 12644.
13. F. C. H. Crick, Acta Crystallogr. 1953, 6, 689; W. H. Landschulz, P. F. Johnson, S. L. McKnight, Science 1988, 240, 1759; E. K. O'Shea, R. Rutkowski, P. S. Kim, ibid. 1989, 243, 538.
14. F. C. H. Crick, Acta Crystallogr. 1953, 6, 689; W. H. Landschulz, P. F. Johnson, S. L. McKnight, Science 1988, 240, 1759; E. K. O'Shea, R. Rutkowski, P. S. Kim, ibid. 1989, 243, 538.
15. F. C. H. Crick, Acta Crystallogr. 1953, 6, 689; W. H. Landschulz, P. F. Johnson, S. L. McKnight, Science 1988, 240, 1759; E. K. O'Shea, R. Rutkowski, P. S. Kim, ibid. 1989, 243, 538.
16. Z. Tuzar, P. Kratochvil in Micelles of Block and Graft Copolymers in Solutions (Surface and Colloid Science, Vol. 15 (Ed.: E. Matijevic)). Plenum Press, New York, 1993, p. 1-85; G. Riess, J. Nervo, D. Rogez, Polym. Eng. Sci. 1977, 8, 634; A. Desjardins, A, Eisenberg, Macromolecules, 1991, 24, 5779; J. M. Denton, D. C. Duecker, E. D. Sprague, J. Phys. Chem. 1993, 97, 756; V. Toncheva, R. Velichkova, G. Trossaert, E. J. Goethals, Polym. Int. 1993, 31, 335.
17. Z. Tuzar, P. Kratochvil in Micelles of Block and Graft Copolymers in Solutions (Surface and Colloid Science, Vol. 15 (Ed.: E. Matijevic)). Plenum Press, New York, 1993, p. 1-85; G. Riess, J. Nervo, D. Rogez, Polym. Eng. Sci. 1977, 8, 634; A. Desjardins, A, Eisenberg, Macromolecules, 1991, 24, 5779; J. M. Denton, D. C. Duecker, E. D. Sprague, J. Phys. Chem. 1993, 97, 756; V. Toncheva, R. Velichkova, G. Trossaert, E. J. Goethals, Polym. Int. 1993, 31, 335.
18. Z. Tuzar, P. Kratochvil in Micelles of Block and Graft Copolymers in Solutions (Surface and Colloid Science, Vol. 15 (Ed.: E. Matijevic)). Plenum Press, New York, 1993, p. 1-85; G. Riess, J. Nervo, D. Rogez, Polym. Eng. Sci. 1977, 8, 634; A. Desjardins, A, Eisenberg, Macromolecules, 1991, 24, 5779; J. M. Denton, D. C. Duecker, E. D. Sprague, J. Phys. Chem. 1993, 97, 756; V. Toncheva, R. Velichkova, G. Trossaert, E. J. Goethals, Polym. Int. 1993, 31, 335.
19. Z. Tuzar, P. Kratochvil in Micelles of Block and Graft Copolymers in Solutions (Surface and Colloid Science, Vol. 15 (Ed.: E. Matijevic)). Plenum Press, New York, 1993, p. 1-85; G. Riess, J. Nervo, D. Rogez, Polym. Eng. Sci. 1977, 8, 634; A. Desjardins, A, Eisenberg, Macromolecules, 1991, 24, 5779; J. M. Denton, D. C. Duecker, E. D. Sprague, J. Phys. Chem. 1993, 97, 756; V. Toncheva, R. Velichkova, G. Trossaert, E. J. Goethals, Polym. Int. 1993, 31, 335.
20. Z. Tuzar, P. Kratochvil in Micelles of Block and Graft Copolymers in Solutions (Surface and Colloid Science, Vol. 15 (Ed.: E. Matijevic)). Plenum Press, New York, 1993, p. 1-85; G. Riess, J. Nervo, D. Rogez, Polym. Eng. Sci. 1977, 8, 634; A. Desjardins, A, Eisenberg, Macromolecules, 1991, 24, 5779; J. M. Denton, D. C. Duecker, E. D. Sprague, J. Phys. Chem. 1993, 97, 756; V. Toncheva, R. Velichkova, G. Trossaert, E. J. Goethals, Polym. Int. 1993, 31, 335.
21. A. M. Liquori, G. Anzuino, V. M. Coiro, M. D'Alagni, P. De Santis, M. Savino, Nature. 1965, 206, 358; E. Schomaker, G. Challa, Macromolecules, 1989, 22, 3337; C. Lavalee, R. E. Prud'homme, ibid. 1989, 22, 2438, and references therein.
22. A. M. Liquori, G. Anzuino, V. M. Coiro, M. D'Alagni, P. De Santis, M. Savino, Nature. 1965, 206, 358; E. Schomaker, G. Challa, Macromolecules, 1989, 22, 3337; C. Lavalee, R. E. Prud'homme, ibid. 1989, 22, 2438, and references therein.
23. A. M. Liquori, G. Anzuino, V. M. Coiro, M. D'Alagni, P. De Santis, M. Savino, Nature. 1965, 206, 358; E. Schomaker, G. Challa, Macromolecules, 1989, 22, 3337; C. Lavalee, R. E. Prud'homme, ibid. 1989, 22, 2438, and references therein.
24. S. Denzinger, A. Dittrich, W. Paulus, H. Ringsdorff in From simplicity to complexity in chemistry - and beyond, Part I (Eds.: A: Müller, A. Dress, F. Vögtle), Vieweg, Braunschweig, 1996, p. 63.
25. H. Matsuura, K. Fukuhara, J. Mol. Struct. 1985, 126, 251; M. J. Hey, S. M. Ilett, G. Davidson, J. Chem. Soc. Faraday Trans. 1995, 91, 3897.
26. H. Matsuura, K. Fukuhara, J. Mol. Struct. 1985, 126, 251; M. J. Hey, S. M. Ilett, G. Davidson, J. Chem. Soc. Faraday Trans. 1995, 91, 3897.
27. B. Chu, G. Wu, Macromol. Symp. 1994, 87, 55, and references therein; K. Mortensen, J. S. Pedersen, Macromolecules, 1993, 26, 805. and references therein; Z. Yang, S. Pickard, N.J. Deng, R. J. Barlow, D. Attwood, C. Booth, Macromolecules, 1994, 27, 2371, and references therein.
28. B. Chu, G. Wu, Macromol. Symp. 1994, 87, 55, and references therein; K. Mortensen, J. S. Pedersen, Macromolecules, 1993, 26, 805. and references therein; Z. Yang, S. Pickard, N.J. Deng, R. J. Barlow, D. Attwood, C. Booth, Macromolecules, 1994, 27, 2371, and references therein.
29. B. Chu, G. Wu, Macromol. Symp. 1994, 87, 55, and references therein; K. Mortensen, J. S. Pedersen, Macromolecules, 1993, 26, 805. and references therein; Z. Yang, S. Pickard, N.J. Deng, R. J. Barlow, D. Attwood, C. Booth, Macromolecules, 1994, 27, 2371, and references therein.
30. The exact experimental data will be published elsewhere.
31. E. J. Corey, K. C. Nicolaou, J. Am. Chem. Soc. 1974, 96, 5614. A 0.03 M solution of the ω-hydroxycarboxylic acid in xylene and 1.5 equiv dithiodipyridine and triphenylphosphane was stirred at room temperature for 40 h. Chromatographic purification gave oxocrown ether 4 in a 50% yield.
32. The same technique has been applied to the cyclization of monosuccinates: A. Bachrach, A. Zilkha, Eur. Polym. J. 1982, 18, 421.
33. A. J, Nijenhuis, D. W Grijpma, A. J. Pennings, Macromolecules 1992, 25, 6419; H. R. Kricheldorf, I. Kreisner-Saunders, C. Boettcher, Polymer 1995, 36, 1252; J. Dahlmann, G. Rafler, Acta Polym. 1993, 44, 103; T. Mathisen, K. Masus. A.-C. Albertsson, Macromolecules 1989, 22, 3842; E. Peeters, H. M. Janssen, M. H. P. van Genderen, E. W. Meijer, Acta Polym. in press.
34. A. J, Nijenhuis, D. W Grijpma, A. J. Pennings, Macromolecules 1992, 25, 6419; H. R. Kricheldorf, I. Kreisner-Saunders, C. Boettcher, Polymer 1995, 36, 1252; J. Dahlmann, G. Rafler, Acta Polym. 1993, 44, 103; T. Mathisen, K. Masus. A.-C. Albertsson, Macromolecules 1989, 22, 3842; E. Peeters, H. M. Janssen, M. H. P. van Genderen, E. W. Meijer, Acta Polym. in press.
35. A. J, Nijenhuis, D. W Grijpma, A. J. Pennings, Macromolecules 1992, 25, 6419; H. R. Kricheldorf, I. Kreisner-Saunders, C. Boettcher, Polymer 1995, 36, 1252; J. Dahlmann, G. Rafler, Acta Polym. 1993, 44, 103; T. Mathisen, K. Masus. A.-C. Albertsson, Macromolecules 1989, 22, 3842; E. Peeters, H. M. Janssen, M. H. P. van Genderen, E. W. Meijer, Acta Polym. in press.
36. A. J, Nijenhuis, D. W Grijpma, A. J. Pennings, Macromolecules 1992, 25, 6419; H. R. Kricheldorf, I. Kreisner-Saunders, C. Boettcher, Polymer 1995, 36, 1252; J. Dahlmann, G. Rafler, Acta Polym. 1993, 44, 103; T. Mathisen, K. Masus. A.-C. Albertsson, Macromolecules 1989, 22, 3842; E. Peeters, H. M. Janssen, M. H. P. van Genderen, E. W. Meijer, Acta Polym. in press.
37. A. J, Nijenhuis, D. W Grijpma, A. J. Pennings, Macromolecules 1992, 25, 6419; H. R. Kricheldorf, I. Kreisner-Saunders, C. Boettcher, Polymer 1995, 36, 1252; J. Dahlmann, G. Rafler, Acta Polym. 1993, 44, 103; T. Mathisen, K. Masus. A.-C. Albertsson, Macromolecules 1989, 22, 3842; E. Peeters, H. M. Janssen, M. H. P. van Genderen, E. W. Meijer, Acta Polym. in press.
38. K. Kalyanasundaram, J. K. Thomas, J. Am. Chem. Soc. 1977, 99, 2039; M. Wilhelm, C.-L. Zhao, Y. Wang, R. Xu, M. A. Winnik, J.-L. Mura, G. Riess, M. D. Croucher, Macromolecule 1991, 24, 1033; I. Astafieva, X. F. Zhong, A. Eisenberg, ibid. 1993, 26, 7339; Polymers 1 und 3 have not yet been analyzed with this technique.
39. K. Kalyanasundaram, J. K. Thomas, J. Am. Chem. Soc. 1977, 99, 2039; M. Wilhelm, C.-L. Zhao, Y. Wang, R. Xu, M. A. Winnik, J.-L. Mura, G. Riess, M. D. Croucher, Macromolecule 1991, 24, 1033; I. Astafieva, X. F. Zhong, A. Eisenberg, ibid. 1993, 26, 7339; Polymers 1 und 3 have not yet been analyzed with this technique.
40. K. Kalyanasundaram, J. K. Thomas, J. Am. Chem. Soc. 1977, 99, 2039; M. Wilhelm, C.-L. Zhao, Y. Wang, R. Xu, M. A. Winnik, J.-L. Mura, G. Riess, M. D. Croucher, Macromolecule 1991, 24, 1033; I. Astafieva, X. F. Zhong, A. Eisenberg, ibid. 1993, 26, 7339; Polymers 1 und 3 have not yet been analyzed with this technique.
41. I. Z. Steinberg, W. F. Harrington, A. Berger, M. Sela, E. Katchalski, J. Am. Chem. Soc. 1960, 82, 5263; E. R. Blout, J. P. Carver, J. Gross, ibid. 1963, 85, 644; W. B. Gratzer, W. Rhodes, D. G. Fasman, Biopolymers 1963, 1, 319; F. M. Pohl, T. M. Jovan, J. Mol. Biol. 1972, 67, 375; R. L. Letsinger, Proc. Robert A. Welch Found, Conf. Chem. Res. 1985, 29, 459; R. Cosstick, F. Eckstein, Biochemistry 1985, 24, 3630; L. P. McIntosh, W. S. Zielinski, B. W. Kalish, G. P. Pfiefer, M. Sprinzl, J. H. van der Sande, T. M. Jovin, ibid. 1985, 24, 4806; Y.-M. Pu, A. F. McDonagh, D. A. Lightner, J. Am. Chem. Soc. 1993, 115, 377.
42. I. Z. Steinberg, W. F. Harrington, A. Berger, M. Sela, E. Katchalski, J. Am. Chem. Soc. 1960, 82, 5263; E. R. Blout, J. P. Carver, J. Gross, ibid. 1963, 85, 644; W. B. Gratzer, W. Rhodes, D. G. Fasman, Biopolymers 1963, 1, 319; F. M. Pohl, T. M. Jovan, J. Mol. Biol. 1972, 67, 375; R. L. Letsinger, Proc. Robert A. Welch Found, Conf. Chem. Res. 1985, 29, 459; R. Cosstick, F. Eckstein, Biochemistry 1985, 24, 3630; L. P. McIntosh, W. S. Zielinski, B. W. Kalish, G. P. Pfiefer, M. Sprinzl, J. H. van der Sande, T. M. Jovin, ibid. 1985, 24, 4806; Y.-M. Pu, A. F. McDonagh, D. A. Lightner, J. Am. Chem. Soc. 1993, 115, 377.
43. I. Z. Steinberg, W. F. Harrington, A. Berger, M. Sela, E. Katchalski, J. Am. Chem. Soc. 1960, 82, 5263; E. R. Blout, J. P. Carver, J. Gross, ibid. 1963, 85, 644; W. B. Gratzer, W. Rhodes, D. G. Fasman, Biopolymers 1963, 1, 319; F. M. Pohl, T. M. Jovan, J. Mol. Biol. 1972, 67, 375; R. L. Letsinger, Proc. Robert A. Welch Found, Conf. Chem. Res. 1985, 29, 459; R. Cosstick, F. Eckstein, Biochemistry 1985, 24, 3630; L. P. McIntosh, W. S. Zielinski, B. W. Kalish, G. P. Pfiefer, M. Sprinzl, J. H. van der Sande, T. M. Jovin, ibid. 1985, 24, 4806; Y.-M. Pu, A. F. McDonagh, D. A. Lightner, J. Am. Chem. Soc. 1993, 115, 377.
44. I. Z. Steinberg, W. F. Harrington, A. Berger, M. Sela, E. Katchalski, J. Am. Chem. Soc. 1960, 82, 5263; E. R. Blout, J. P. Carver, J. Gross, ibid. 1963, 85, 644; W. B. Gratzer, W. Rhodes, D. G. Fasman, Biopolymers 1963, 1, 319; F. M. Pohl, T. M. Jovan, J. Mol. Biol. 1972, 67, 375; R. L. Letsinger, Proc. Robert A. Welch Found, Conf. Chem. Res. 1985, 29, 459; R. Cosstick, F. Eckstein, Biochemistry 1985, 24, 3630; L. P. McIntosh, W. S. Zielinski, B. W. Kalish, G. P. Pfiefer, M. Sprinzl, J. H. van der Sande, T. M. Jovin, ibid. 1985, 24, 4806; Y.-M. Pu, A. F. McDonagh, D. A. Lightner, J. Am. Chem. Soc. 1993, 115, 377.
45. I. Z. Steinberg, W. F. Harrington, A. Berger, M. Sela, E. Katchalski, J. Am. Chem. Soc. 1960, 82, 5263; E. R. Blout, J. P. Carver, J. Gross, ibid. 1963, 85, 644; W. B. Gratzer, W. Rhodes, D. G. Fasman, Biopolymers 1963, 1, 319; F. M. Pohl, T. M. Jovan, J. Mol. Biol. 1972, 67, 375; R. L. Letsinger, Proc. Robert A. Welch Found, Conf. Chem. Res. 1985, 29, 459; R. Cosstick, F. Eckstein, Biochemistry 1985, 24, 3630; L. P. McIntosh, W. S. Zielinski, B. W. Kalish, G. P. Pfiefer, M. Sprinzl, J. H. van der Sande, T. M. Jovin, ibid. 1985, 24, 4806; Y.-M. Pu, A. F. McDonagh, D. A. Lightner, J. Am. Chem. Soc. 1993, 115, 377.
46. I. Z. Steinberg, W. F. Harrington, A. Berger, M. Sela, E. Katchalski, J. Am. Chem. Soc. 1960, 82, 5263; E. R. Blout, J. P. Carver, J. Gross, ibid. 1963, 85, 644; W. B. Gratzer, W. Rhodes, D. G. Fasman, Biopolymers 1963, 1, 319; F. M. Pohl, T. M. Jovan, J. Mol. Biol. 1972, 67, 375; R. L. Letsinger, Proc. Robert A. Welch Found, Conf. Chem. Res. 1985, 29, 459; R. Cosstick, F. Eckstein, Biochemistry 1985, 24, 3630; L. P. McIntosh, W. S. Zielinski, B. W. Kalish, G. P. Pfiefer, M. Sprinzl, J. H. van der Sande, T. M. Jovin, ibid. 1985, 24, 4806; Y.-M. Pu, A. F. McDonagh, D. A. Lightner, J. Am. Chem. Soc. 1993, 115, 377.
47. I. Z. Steinberg, W. F. Harrington, A. Berger, M. Sela, E. Katchalski, J. Am. Chem. Soc. 1960, 82, 5263; E. R. Blout, J. P. Carver, J. Gross, ibid. 1963, 85, 644; W. B. Gratzer, W. Rhodes, D. G. Fasman, Biopolymers 1963, 1, 319; F. M. Pohl, T. M. Jovan, J. Mol. Biol. 1972, 67, 375; R. L. Letsinger, Proc. Robert A. Welch Found, Conf. Chem. Res. 1985, 29, 459; R. Cosstick, F. Eckstein, Biochemistry 1985, 24, 3630; L. P. McIntosh, W. S. Zielinski, B. W. Kalish, G. P. Pfiefer, M. Sprinzl, J. H. van der Sande, T. M. Jovin, ibid. 1985, 24, 4806; Y.-M. Pu, A. F. McDonagh, D. A. Lightner, J. Am. Chem. Soc. 1993, 115, 377.
48. I. Z. Steinberg, W. F. Harrington, A. Berger, M. Sela, E. Katchalski, J. Am. Chem. Soc. 1960, 82, 5263; E. R. Blout, J. P. Carver, J. Gross, ibid. 1963, 85, 644; W. B. Gratzer, W. Rhodes, D. G. Fasman, Biopolymers 1963, 1, 319; F. M. Pohl, T. M. Jovan, J. Mol. Biol. 1972, 67, 375; R. L. Letsinger, Proc. Robert A. Welch Found, Conf. Chem. Res. 1985, 29, 459; R. Cosstick, F. Eckstein, Biochemistry 1985, 24, 3630; L. P. McIntosh, W. S. Zielinski, B. W. Kalish, G. P. Pfiefer, M. Sprinzl, J. H. van der Sande, T. M. Jovin, ibid. 1985, 24, 4806; Y.-M. Pu, A. F. McDonagh, D. A. Lightner, J. Am. Chem. Soc. 1993, 115, 377.
49. B. Tümmler, G. Maass, E. Weber, W. Wehner, F. Vögtle, J. Am. Chem. Soc. 1977, 99, 14683; B. Tümmler, G. Maass, F. Vögtle, H. Sieger, U. Heimann, E. Weber, ibid. 1979, 101, 10, 2588; F. Vögtle, H. Sieger. Angew. Chem. 1977. 89, 410; Angew. Chem. Int. Ed. Engl. 1977, 16, 396; F. Vögtle, H. Sieger, ibid. 1978, 90, 212; W. Saenger, H. Brand, F. Vögtle, E. Weber in Metal-ligand interactions in organic chemisiry and biochemistry (Eds. : B. Pullman, N. Goldblum). Reidel, Dordrecht, 1977. p. 363.
50. B. Tümmler, G. Maass, E. Weber, W. Wehner, F. Vögtle, J. Am. Chem. Soc. 1977, 99, 14683; B. Tümmler, G. Maass, F. Vögtle, H. Sieger, U. Heimann, E. Weber, ibid. 1979, 101, 10, 2588; F. Vögtle, H. Sieger. Angew. Chem. 1977. 89, 410; Angew. Chem. Int. Ed. Engl. 1977, 16, 396; F. Vögtle, H. Sieger, ibid. 1978, 90, 212; W. Saenger, H. Brand, F. Vögtle, E. Weber in Metal-ligand interactions in organic chemisiry and biochemistry (Eds. : B. Pullman, N. Goldblum). Reidel, Dordrecht, 1977. p. 363.
51. B. Tümmler, G. Maass, E. Weber, W. Wehner, F. Vögtle, J. Am. Chem. Soc. 1977, 99, 14683; B. Tümmler, G. Maass, F. Vögtle, H. Sieger, U. Heimann, E. Weber, ibid. 1979, 101, 10, 2588; F. Vögtle, H. Sieger. Angew. Chem. 1977. 89, 410; Angew. Chem. Int. Ed. Engl. 1977, 16, 396; F. Vögtle, H. Sieger, ibid. 1978, 90, 212; W. Saenger, H. Brand, F. Vögtle, E. Weber in Metal-ligand interactions in organic chemisiry and biochemistry (Eds. : B. Pullman, N. Goldblum). Reidel, Dordrecht, 1977. p. 363.
52. B. Tümmler, G. Maass, E. Weber, W. Wehner, F. Vögtle, J. Am. Chem. Soc. 1977, 99, 14683; B. Tümmler, G. Maass, F. Vögtle, H. Sieger, U. Heimann, E. Weber, ibid. 1979, 101, 10, 2588; F. Vögtle, H. Sieger. Angew. Chem. 1977. 89, 410; Angew. Chem. Int. Ed. Engl. 1977, 16, 396; F. Vögtle, H. Sieger, ibid. 1978, 90, 212; W. Saenger, H. Brand, F. Vögtle, E. Weber in Metal-ligand interactions in organic chemisiry and biochemistry (Eds. : B. Pullman, N. Goldblum). Reidel, Dordrecht, 1977. p. 363.
53. B. Tümmler, G. Maass, E. Weber, W. Wehner, F. Vögtle, J. Am. Chem. Soc. 1977, 99, 14683; B. Tümmler, G. Maass, F. Vögtle, H. Sieger, U. Heimann, E. Weber, ibid. 1979, 101, 10, 2588; F. Vögtle, H. Sieger. Angew. Chem. 1977. 89, 410; Angew. Chem. Int. Ed. Engl. 1977, 16, 396; F. Vögtle, H. Sieger, ibid. 1978, 90, 212; W. Saenger, H. Brand, F. Vögtle, E. Weber in Metal-ligand interactions in organic chemisiry and biochemistry (Eds. : B. Pullman, N. Goldblum). Reidel, Dordrecht, 1977. p. 363.
54. B. Tümmler, G. Maass, E. Weber, W. Wehner, F. Vögtle, J. Am. Chem. Soc. 1977, 99, 14683; B. Tümmler, G. Maass, F. Vögtle, H. Sieger, U. Heimann, E. Weber, ibid. 1979, 101, 10, 2588; F. Vögtle, H. Sieger. Angew. Chem. 1977. 89, 410; Angew. Chem. Int. Ed. Engl. 1977, 16, 396; F. Vögtle, H. Sieger, ibid. 1978, 90, 212; W. Saenger, H. Brand, F. Vögtle, E. Weber in Metal-ligand interactions in organic chemisiry and biochemistry (Eds. : B. Pullman, N. Goldblum). Reidel, Dordrecht, 1977. p. 363.
55. 3OD).
56. This hypothesis is in agreement with the fact that the balance between stereoelectronic gauche effects and electrostatic repulsion, which depends on the solvent applied, directs PEO structures into helical conformations in aqueous solutions: A. Abe, J. E. Mark, J. Am. Chem. Soc. 1976, 95, 6468; G. D. Smith, D. Y. Yoon, R. L Jaffe, Macromolecules 1993, 26, 5213, and references therein.
57. This hypothesis is in agreement with the fact that the balance between stereoelectronic gauche effects and electrostatic repulsion, which depends on the solvent applied, directs PEO structures into helical conformations in aqueous solutions: A. Abe, J. E. Mark, J. Am. Chem. Soc. 1976, 95, 6468; G. D. Smith, D. Y. Yoon, R. L Jaffe, Macromolecules 1993, 26, 5213, and references therein.
58. For steps a) and b), see K. Mori, Tetrahedron, 1976, 32, 1101.