'Smart' rotaxanes: Shape memory and control in tertiary amide peptido[2]rotaxanes

Journal of the American Chemical Society

Volumn 121, Issue 17, 1999, Pages 4124-4129

  Clegg, William ^b,c   Gimenez Saiz, Carlos ^d   Leigh, David A ^a   Murphy, Aden ^a   Slawin, Alexandra M Z ^d   Teat, Simon J ^b,c  

^a UNIVERSITY OF WARWICK   (United Kingdom)

^b NEWCASTLE UNIVERSITY   (United Kingdom)

^c DARESBURY LABORATORY   (United Kingdom)

^d NONE

Author keywords

[No Author keywords available]

Indexed keywords

SOLVENT; TAXANE DERIVATIVE; TERTIARY AMINE;

AMINO ACID SEQUENCE; ARTICLE; CHEMICAL ANALYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN CONFORMATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0033526329     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9841310     Document Type: Article

References (63)

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28. For examples of rotaxanes where intramolecular interactions bring about changes in the photochemical and/or electrochemical behavior of the individual components see ref 2g or: Amabilino, D. B.; Ashton, P. R.; Balzani, V.; Brown, C. L.; Credi, A.; Fréchet, J. M. J.; Leon, J. W.; Raymo, F. M.; Spencer, N.; Stoddart, J. F.; Venturi, M. J. Am. Chem. Soc. 1996, 118, 12012-12020 and references therein.
29. For hydrogen bond-assembled host-guest complexes which stabilize a particular secondary amide bond rotamer see: (a) Vicent, C.; Hirst, S. C.; Garcia-Tellado, F.; Hamilton, A. D. J. Am. Chem. Soc. 1991, 113, 5466-5467. (b) Pernía, G. J.; Kilburn, J. D.; Essex, J. W.; Mortishire-Smith, R. J.; Rowley, M. J. Am. Chem. Soc. 1996, 118, 10220-10227. (c) Moraczewski, A. L.; Banaszynski, L. A.; From, A. M.; White, C. E.; Smith, B. D. J. Org. Chem. 1998, 63, 7258-7262.
30. For hydrogen bond-assembled host-guest complexes which stabilize a particular secondary amide bond rotamer see: (a) Vicent, C.; Hirst, S. C.; Garcia-Tellado, F.; Hamilton, A. D. J. Am. Chem. Soc. 1991, 113, 5466- 5467. (b) Pernía, G. J.; Kilburn, J. D.; Essex, J. W.; Mortishire-Smith, R. J.; Rowley, M. J. Am. Chem. Soc. 1996, 118, 10220-10227. (c) Moraczewski, A. L.; Banaszynski, L. A.; From, A. M.; White, C. E.; Smith, B. D. J. Org. Chem. 1998, 63, 7258-7262.
31. For hydrogen bond-assembled host-guest complexes which stabilize a particular secondary amide bond rotamer see: (a) Vicent, C.; Hirst, S. C.; Garcia-Tellado, F.; Hamilton, A. D. J. Am. Chem. Soc. 1991, 113, 5466- 5467. (b) Pernía, G. J.; Kilburn, J. D.; Essex, J. W.; Mortishire-Smith, R. J.; Rowley, M. J. Am. Chem. Soc. 1996, 118, 10220-10227. (c) Moraczewski, A. L.; Banaszynski, L. A.; From, A. M.; White, C. E.; Smith, B. D. J. Org. Chem. 1998, 63, 7258-7262.
32. For control over the shape of macromolecules with flexible backbones through intramolecular interactions see: Percec, V.; Ahn, C.-H.; Ungar, G.; Yeardley, D. J. P.; Möller, M.; Sheiko, S. S. Nature 1998, 391, 161-164.
33. For a comprehensive account of smart materials with a recoverable inherent or predetermined shape, function, or property see: Shape Memory Materials; Otsuka, K., Wayman, C. M., Eds.; Cambridge University Press: Cambridge, 1998. For other conformationally switchable molecules which respond to changes in their environment see: (a) Höger, S.; Enkelmann, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 2713-2716. (b) Höger, S.; Meckenstock, A. D.; Muller, S. Chem. Eur. J. 1998, 4, 2423-2434. (c) Leigh, D. A.; Moody, K.; Smart, J. P.; Watson, K. J.; Slawin, A. M. Z. Angew. Chem., Int. Ed. Engl. 1996, 35, 306-310. (d) Janout, V.; Lanier, M.; Regen, S. L. J. Am. Chem. Soc. 1996, 118, 1573-1574. (e) Janout, V.; Lanier, M.; Regen, S. L. J. Am. Chem. Soc. 1997, 119, 640-647.
34. For a comprehensive account of smart materials with a recoverable inherent or predetermined shape, function, or property see: Shape Memory Materials; Otsuka, K., Wayman, C. M., Eds.; Cambridge University Press: Cambridge, 1998. For other conformationally switchable molecules which respond to changes in their environment see: (a) Höger, S.; Enkelmann, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 2713-2716. (b) Höger, S.; Meckenstock, A. D.; Muller, S. Chem. Eur. J. 1998, 4, 2423-2434. (c) Leigh, D. A.; Moody, K.; Smart, J. P.; Watson, K. J.; Slawin, A. M. Z. Angew. Chem., Int. Ed. Engl. 1996, 35, 306-310. (d) Janout, V.; Lanier, M.; Regen, S. L. J. Am. Chem. Soc. 1996, 118, 1573-1574. (e) Janout, V.; Lanier, M.; Regen, S. L. J. Am. Chem. Soc. 1997, 119, 640-647.
35. For a comprehensive account of smart materials with a recoverable inherent or predetermined shape, function, or property see: Shape Memory Materials; Otsuka, K., Wayman, C. M., Eds.; Cambridge University Press: Cambridge, 1998. For other conformationally switchable molecules which respond to changes in their environment see: (a) Höger, S.; Enkelmann, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 2713-2716. (b) Höger, S.; Meckenstock, A. D.; Muller, S. Chem. Eur. J. 1998, 4, 2423-2434. (c) Leigh, D. A.; Moody, K.; Smart, J. P.; Watson, K. J.; Slawin, A. M. Z. Angew. Chem., Int. Ed. Engl. 1996, 35, 306-310. (d) Janout, V.; Lanier, M.; Regen, S. L. J. Am. Chem. Soc. 1996, 118, 1573-1574. (e) Janout, V.; Lanier, M.; Regen, S. L. J. Am. Chem. Soc. 1997, 119, 640-647.
36. For a comprehensive account of smart materials with a recoverable inherent or predetermined shape, function, or property see: Shape Memory Materials; Otsuka, K., Wayman, C. M., Eds.; Cambridge University Press: Cambridge, 1998. For other conformationally switchable molecules which respond to changes in their environment see: (a) Höger, S.; Enkelmann, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 2713-2716. (b) Höger, S.; Meckenstock, A. D.; Muller, S. Chem. Eur. J. 1998, 4, 2423-2434. (c) Leigh, D. A.; Moody, K.; Smart, J. P.; Watson, K. J.; Slawin, A. M. Z. Angew. Chem., Int. Ed. Engl. 1996, 35, 306-310. (d) Janout, V.; Lanier, M.; Regen, S. L. J. Am. Chem. Soc. 1996, 118, 1573-1574. (e) Janout, V.; Lanier, M.; Regen, S. L. J. Am. Chem. Soc. 1997, 119, 640-647.
37. For a comprehensive account of smart materials with a recoverable inherent or predetermined shape, function, or property see: Shape Memory Materials; Otsuka, K., Wayman, C. M., Eds.; Cambridge University Press: Cambridge, 1998. For other conformationally switchable molecules which respond to changes in their environment see: (a) Höger, S.; Enkelmann, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 2713-2716. (b) Höger, S.; Meckenstock, A. D.; Muller, S. Chem. Eur. J. 1998, 4, 2423-2434. (c) Leigh, D. A.; Moody, K.; Smart, J. P.; Watson, K. J.; Slawin, A. M. Z. Angew. Chem., Int. Ed. Engl. 1996, 35, 306-310. (d) Janout, V.; Lanier, M.; Regen, S. L. J. Am. Chem. Soc. 1996, 118, 1573-1574. (e) Janout, V.; Lanier, M.; Regen, S. L. J. Am. Chem. Soc. 1997, 119, 640-647.
38. For a comprehensive account of smart materials with a recoverable inherent or predetermined shape, function, or property see: Shape Memory Materials; Otsuka, K., Wayman, C. M., Eds.; Cambridge University Press: Cambridge, 1998. For other conformationally switchable molecules which respond to changes in their environment see: (a) Höger, S.; Enkelmann, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 2713-2716. (b) Höger, S.; Meckenstock, A. D.; Muller, S. Chem. Eur. J. 1998, 4, 2423-2434. (c) Leigh, D. A.; Moody, K.; Smart, J. P.; Watson, K. J.; Slawin, A. M. Z. Angew. Chem., Int. Ed. Engl. 1996, 35, 306-310. (d) Janout, V.; Lanier, M.; Regen, S. L. J. Am. Chem. Soc. 1996, 118, 1573-1574. (e) Janout, V.; Lanier, M.; Regen, S. L. J. Am. Chem. Soc. 1997, 119, 640-647.
39. For other amide-based rotaxanes see: Vögtle, F.; Dünnwald, T.; Schmidt T. Acc. Chem. Res. 1996, 29, 451-460.
40. The preference of pyridine-2,6-dicarbamido units for a syn conformation with two intramolecular NH⋯N(pyr) hydrogen bonds is now well established [Newkome, G. R.; Fronczek, F. R.; Kohli, D. K. Acta Crystallogr. 1981, B37, 2114-2117. Hunter, C. A.; Purvis, D. H. Angew. Chem., Int. Ed. Engl. 1992, 31, 792-795. Johnston, A. G.; Leigh, D. A.; Nezhat, L.; Smart, J. P.; Deegan, M. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1212-1216. Hamuro, Y.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Sec. 1997, 119, 10587-10593]. This reduces the number of low-energy conformations available to the macrocycle and, in particular, dramatically increases the energy required to make the kind of out-of-plane distortions required of the aromatic dicarbonyl system to accommodate steric hindrances around the hydrogen bonding template sites.
41. The preference of pyridine-2,6-dicarbamido units for a syn conformation with two intramolecular NH⋯N(pyr) hydrogen bonds is now well established [Newkome, G. R.; Fronczek, F. R.; Kohli, D. K. Acta Crystallogr. 1981, B37, 2114-2117. Hunter, C. A.; Purvis, D. H. Angew. Chem., Int. Ed. Engl. 1992, 31, 792-795. Johnston, A. G.; Leigh, D. A.; Nezhat, L.; Smart, J. P.; Deegan, M. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1212-1216. Hamuro, Y.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Sec. 1997, 119, 10587-10593]. This reduces the number of low-energy conformations available to the macrocycle and, in particular, dramatically increases the energy required to make the kind of out-of-plane distortions required of the aromatic dicarbonyl system to accommodate steric hindrances around the hydrogen bonding template sites.
42. The preference of pyridine-2,6-dicarbamido units for a syn conformation with two intramolecular NH⋯N(pyr) hydrogen bonds is now well established [Newkome, G. R.; Fronczek, F. R.; Kohli, D. K. Acta Crystallogr. 1981, B37, 2114-2117. Hunter, C. A.; Purvis, D. H. Angew. Chem., Int. Ed. Engl. 1992, 31, 792-795. Johnston, A. G.; Leigh, D. A.; Nezhat, L.; Smart, J. P.; Deegan, M. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1212-1216. Hamuro, Y.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Sec. 1997, 119, 10587-10593]. This reduces the number of low-energy conformations available to the macrocycle and, in particular, dramatically increases the energy required to make the kind of out-of-plane distortions required of the aromatic dicarbonyl system to accommodate steric hindrances around the hydrogen bonding template sites.
43. The preference of pyridine-2,6-dicarbamido units for a syn conformation with two intramolecular NH⋯N(pyr) hydrogen bonds is now well established [Newkome, G. R.; Fronczek, F. R.; Kohli, D. K. Acta Crystallogr. 1981, B37, 2114-2117. Hunter, C. A.; Purvis, D. H. Angew. Chem., Int. Ed. Engl. 1992, 31, 792-795. Johnston, A. G.; Leigh, D. A.; Nezhat, L.; Smart, J. P.; Deegan, M. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1212-1216. Hamuro, Y.; Geib, S. J.; Hamilton, A. D. J. Am. Chem. Sec. 1997, 119, 10587-10593]. This reduces the number of low-energy conformations available to the macrocycle and, in particular, dramatically increases the energy required to make the kind of out-of-plane distortions required of the aromatic dicarbonyl system to accommodate steric hindrances around the hydrogen bonding template sites.
44. "Co-conformation" refers to the relative positions and orientations of the mechanically interlocked components with respect to each other [Fyfe, M. C. T.; Glink, P. T.; Menzer, S.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 2068-2069].
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47. b in ROESY experiments. Similarly, in the minor, Z, isomer a strong enhancement was observed between Hb′ and Hc′.
48. This is consistent with conformational studies on other tertiary amides, e.g.: LaPlanche, L. A.; Rogers, M. T. J. Am. Chem. Soc. 1963, 85, 3728-3730. The major rotamers observed in all the threads and rotaxanes reported here were found to be E by ROESY experiments.
49. The extent of deshielding is much less than that for the same proton in the glycylglycine system [ref 3f], suggesting a greater population of macrocycle conformations with all four amide carbonyls exo to the cavity.
50. For other examples of the stabilization of tertiary amide rotamers by intramolecular hydrogen bonding see: (a) Madison, V.; Atreyi, M.; Deber, C. M.; Blout, E. R. J. Am. Chem. Soc. 1974, 96, 6725-6734. (b) Tamaki, M.; Komiya, S.; Yabu, M.; Watanabe, E.; Akabori, S.; Muramatsu, I. J. Chem. Soc., Perkin Trans. 1 1997, 3497-3500.
51. For other examples of the stabilization of tertiary amide rotamers by intramolecular hydrogen bonding see: (a) Madison, V.; Atreyi, M.; Deber, C. M.; Blout, E. R. J. Am. Chem. Soc. 1974, 96, 6725-6734. (b) Tamaki, M.; Komiya, S.; Yabu, M.; Watanabe, E.; Akabori, S.; Muramatsu, I. J. Chem. Soc., Perkin Trans. 1 1997, 3497-3500.
52. -1 at 298 K [refs 17 and 18]. The other rotaxanes are not soluble below the coalescence temperatures of the exchange phenomena.
53. Calculated from the coalescence temperature using a modified Eyring equation [Shanan-Atidi, H.; Bari-Eli, K. H. J. Phys. Chem. 1970, 74, 961-963].
54. For an account of the SPT-SIR technique applied to catenane architectures see: (a) Leigh, D. A.; Murphy, A.; Smart, J. P.; Deleuze, M. S.; Zerbetto F. J. Am. Chem. Soc. 1998, 120, 6458-6467. For recent examples of SPT-SIR in other systems see: (b) Ben-David Blanca, M.; Maimon, E.; Kost, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 2216-2219. (c) Kelly, T. R.; Tellitu, I.; Sestelo, J. P. Angew. Chem., Int. Ed. Engl. 1997, 36, 1866-1868. (d) Abdourazak, A. H.; Sygula, S.; Rabideau, P. W. J. Am. Chem. Soc. 1993, 115, 3010-3011. (e) Frim, R.; Zilber, G.; Rabinovitz, M. J. Chem. Soc. Chem. Commun. 1991, 1202-1203. For a review of 2D methods for determining the kinetics of exchange processes see: (f) Perrin, C. L.; Dwyer, T. J. Chem. Rev. 1990, 90, 935-967.
55. For an account of the SPT-SIR technique applied to catenane architectures see: (a) Leigh, D. A.; Murphy, A.; Smart, J. P.; Deleuze, M. S.; Zerbetto F. J. Am. Chem. Soc. 1998, 120, 6458-6467. For recent examples of SPT-SIR in other systems see: (b) Ben-David Blanca, M.; Maimon, E.; Kost, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 2216-2219. (c) Kelly, T. R.; Tellitu, I.; Sestelo, J. P. Angew. Chem., Int. Ed. Engl. 1997, 36, 1866-1868. (d) Abdourazak, A. H.; Sygula, S.; Rabideau, P. W. J. Am. Chem. Soc. 1993, 115, 3010-3011. (e) Frim, R.; Zilber, G.; Rabinovitz, M. J. Chem. Soc. Chem. Commun. 1991, 1202-1203. For a review of 2D methods for determining the kinetics of exchange processes see: (f) Perrin, C. L.; Dwyer, T. J. Chem. Rev. 1990, 90, 935-967.
56. For an account of the SPT-SIR technique applied to catenane architectures see: (a) Leigh, D. A.; Murphy, A.; Smart, J. P.; Deleuze, M. S.; Zerbetto F. J. Am. Chem. Soc. 1998, 120, 6458-6467. For recent examples of SPT-SIR in other systems see: (b) Ben-David Blanca, M.; Maimon, E.; Kost, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 2216-2219. (c) Kelly, T. R.; Tellitu, I.; Sestelo, J. P. Angew. Chem., Int. Ed. Engl. 1997, 36, 1866-1868. (d) Abdourazak, A. H.; Sygula, S.; Rabideau, P. W. J. Am. Chem. Soc. 1993, 115, 3010-3011. (e) Frim, R.; Zilber, G.; Rabinovitz, M. J. Chem. Soc. Chem. Commun. 1991, 1202-1203. For a review of 2D methods for determining the kinetics of exchange processes see: (f) Perrin, C. L.; Dwyer, T. J. Chem. Rev. 1990, 90, 935-967.
57. For an account of the SPT-SIR technique applied to catenane architectures see: (a) Leigh, D. A.; Murphy, A.; Smart, J. P.; Deleuze, M. S.; Zerbetto F. J. Am. Chem. Soc. 1998, 120, 6458-6467. For recent examples of SPT-SIR in other systems see: (b) Ben-David Blanca, M.; Maimon, E.; Kost, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 2216-2219. (c) Kelly, T. R.; Tellitu, I.; Sestelo, J. P. Angew. Chem., Int. Ed. Engl. 1997, 36, 1866-1868. (d) Abdourazak, A. H.; Sygula, S.; Rabideau, P. W. J. Am. Chem. Soc. 1993, 115, 3010-3011. (e) Frim, R.; Zilber, G.; Rabinovitz, M. J. Chem. Soc. Chem. Commun. 1991, 1202-1203. For a review of 2D methods for determining the kinetics of exchange processes see: (f) Perrin, C. L.; Dwyer, T. J. Chem. Rev. 1990, 90, 935-967.
58. For an account of the SPT-SIR technique applied to catenane architectures see: (a) Leigh, D. A.; Murphy, A.; Smart, J. P.; Deleuze, M. S.; Zerbetto F. J. Am. Chem. Soc. 1998, 120, 6458-6467. For recent examples of SPT-SIR in other systems see: (b) Ben-David Blanca, M.; Maimon, E.; Kost, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 2216-2219. (c) Kelly, T. R.; Tellitu, I.; Sestelo, J. P. Angew. Chem., Int. Ed. Engl. 1997, 36, 1866-1868. (d) Abdourazak, A. H.; Sygula, S.; Rabideau, P. W. J. Am. Chem. Soc. 1993, 115, 3010-3011. (e) Frim, R.; Zilber, G.; Rabinovitz, M. J. Chem. Soc. Chem. Commun. 1991, 1202-1203. For a review of 2D methods for determining the kinetics of exchange processes see: (f) Perrin, C. L.; Dwyer, T. J. Chem. Rev. 1990, 90, 935-967.
59. For an account of the SPT-SIR technique applied to catenane architectures see: (a) Leigh, D. A.; Murphy, A.; Smart, J. P.; Deleuze, M. S.; Zerbetto F. J. Am. Chem. Soc. 1998, 120, 6458-6467. For recent examples of SPT-SIR in other systems see: (b) Ben-David Blanca, M.; Maimon, E.; Kost, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 2216-2219. (c) Kelly, T. R.; Tellitu, I.; Sestelo, J. P. Angew. Chem., Int. Ed. Engl. 1997, 36, 1866-1868. (d) Abdourazak, A. H.; Sygula, S.; Rabideau, P. W. J. Am. Chem. Soc. 1993, 115, 3010-3011. (e) Frim, R.; Zilber, G.; Rabinovitz, M. J. Chem. Soc. Chem. Commun. 1991, 1202-1203. For a review of 2D methods for determining the kinetics of exchange processes see: (f) Perrin, C. L.; Dwyer, T. J. Chem. Rev. 1990, 90, 935-967.
60. For steric effects on tertiary amide rotamer equilibria see: Beausoleil, E.; Lubell, W. D. J. Am. Chem. Soc. 1996, 118, 12902-12908 and references therein.
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