A reversible synthetic rotary molecular motor

Science

Volumn 306, Issue 5701, 2004, Pages 1532-1537

  Hernández, José V ^a   Kay, Euan R ^a   Leigh, David A ^a  

^a UNIVERSITY OF EDINBURGH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BROWNIAN MOVEMENT; ROTATION;

CHEMICAL TRANSFORMATIONS; MOLECULAR MOTORS; POSITIONAL DISPLACEMENTS;

MOLECULAR STRUCTURE;

ADENOSINE TRIPHOSPHATE; AMINO ACID; CATENANE; MALEIMIDE; MOLECULAR MOTOR; ROTAXANE;

MOLECULAR ANALYSIS;

ARTICLE; BINDING SITE; CHEMICAL STRUCTURE; ENERGY; MOTION; PHOTODYNAMICS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; ROTATION; THERMODYNAMICS;

BINDING SITES; CATENANES; CHEMISTRY, PHYSICAL; ISOMERISM; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; MOLECULAR MOTOR PROTEINS; MOLECULAR STRUCTURE; MOTION; ROTATION; THERMODYNAMICS;

EID: 9444256373     PISSN: 00368075     EISSN: None     Source Type: Journal    
DOI: 10.1126/science.1103949     Document Type: Article

References (43)

1. E. M. Purcell, Am. J. Phys. 45, 3 (1977).
2. M. Schliwa, Ed., Molecular Motors (Wiley-VCH, Weinheim, Germany, 2003).
3. P. D. Boyer, Angew. Chem. Int. Ed. 37, 2296 (1998).
4. R. P. Feynman, R. B. Leighton, M. Sands, The Feynman Lectures on Physics (Addison-Wesley, Reading, MA, 1963), vol. 1, chap. 46.
5. M. von Smoluchowski, Physik. Zeitschr. 13, 1069 (1912).
6. T. R. Kelly, I. Tellitu, J. P. Sestelo, Angew. Chem. Int. Ed. Engl. 36, 1866 (1997).
7. A. P. Davis, Angew. Chem. Int. Ed. 37, 909 (1998).
8. V. Balzani, A. Credi, F. M. Raymo, J. F. Stoddart, Angew. Chem. Int. Ed. 39, 3349 (2000).
9. M. F. Hawthorne et al., Science 303, 1849 (2004).
10. C. P. Mandl, B. König, Angew. Chem. Int. Ed. 43, 1622 (2004).
11. T. R. Kelly, H. De Silva, R. A. Silva, Nature 401, 150 (1999).
12. T. R. Kelly, R. A. Silva, H. De Silva, S. Jasmin, Y. J. Zhao, J. Am. Chem. Soc. 122, 6935 (2000).
13. N. Koumura, R. W. J. Zijlstra, R. A. van Delden, N. Harada, B. L. Feringa, Nature 401, 152 (1999).
14. N. Koumura, E. M. Ceertsema, M. B. van Gelder, A. Meetsma, B. L. Feringa, J. Am. Chem. Soc. 124, 5037 (2002).
15. M. K. J. ter Wiel, R. A. van Delden, A. Meetsma, B. L. Feringa, J. Am. Chem. Soc. 125, 15076 (2003).
16. R. A. van Delden, M. K. J. ter Wiel, H. De Jong, A. Meetsma, B. L. Feringa, Org. Biomol. Chem. 2, 1531 (2004).
17. D. A. Leigh, J. K. Y. Wong, F. Dehez, F. Zerbetto, Nature 424, 174 (2003).
18. P. Reimann, Phys. Rep. 361, 57 (2002).
19. J. M. R. Parrondo, L. Dinis, Contemp. Phys. 45, 147 (2004).
20. R. D. Astumian, Science 276, 917 (1997).
21. Randomizing influences other than Brownian motion can be used in ratchet mechanisms. For example, in quantum ratchets, quantum effects such as tunneling play this role.
22. The principle of detailed balance (23) tells us that no net task can be performed by the fluxional exchange of components at equilibrium, because transitions take place at the same rate in opposite directions. The structure of catenane 1 is remarkable in that it separates the kinetic (ability to exchange) and thermodynamic (impetus for net transport) requirements for detailed balance.
23. L. Onsager, Phys. Rev. 37, 405 (1931).
24. R. D. Astumian, P. Hänggi, Phys. Today 55, 33 (November 2002).
25. R. D. Astumian, I. Derényi, Eur. Biophys. J. 27, 474 (1998).
26. Special issue on quot;Ratchets and Brownian Motors: Basics, Experiments and Applications,quot; H. Linke, Ed., Appl. Phys. A 75, 167 (2002).
27. G. Oster, H. Y. Wang, Trends Cell Biol. 13, 114 (2003).
28. J. Rousselet, L. Salome, A. Ajdari, J. Prost, Nature 370, 446 (1994).
29. L. P. Faucheux, L. S. Bourdieu, P. D. Kaplan, A. J. Libchaber, Phys. Rev. Lett. 74, 1504 (1995).
30. J. S. Bader et al., Proc. Natl. Acad. Sci. U.S.A. 96, 13165 (1999).
31. S. Matthias, F. Müller, Nature 424, 53 (2003).
32. A. Altieri et al., Angew. Chem. Int. Ed. 42, 2296 (2003).
33. The prefix indicates the position of the smaller macrocycle on the larger one.
34. Although catenane fum-E-1 was originally prepared as its O-t-butyldiphenylsilyl (TBDPS) derivative, the steric bulk caused low yields during the re-silylation protocol of step k, so it was replaced with the smaller TBDMS group for all the directional rotation studies.
35. Materials and methods are available as supporting material on Science Online.
36. The photoisomerization reaction gives a 50:50 E:Z mixture in the photostationary state. No accompanying photodegradation or decomposition was detected (37).
37. F. G. Gatti et al., Proc. Natl. Acad. Sci. U.S.A. 100,10 (2003).
38. By raising or lowering the energy minima, the balance-breaking reactions intrinsically affect the kinetic barriers as well.
39. This is not quite as simple as the ΔG values of the forward and reverse covalent bond forming and breaking reactions canceling each other out. When unlinking takes place, the restriction in freedom of movement reduces the entropy of the small macrocycle in addition to the ΔG change associated with the chemical reaction; however, when linking occurs, the entropy increases by the same amount.
40. Certain aspects of Feynman's discussion of the ratchet and pawl as a motor have been shown to be flawed (41, 42).
41. J. M. R. Parrondo, P. Español, Am. J. Phys. 64, 1125 (1996).
42. M. O. Magnasco, G. Stolovitzky, J. Stat. Phys. 93, 615 (1998).
43. This work was supported by the Carnegie Trust (a scholarship to E.R.K.) and the European Union (a Marie Curie Fellowship to J.V.H.).