Synthesis of a molecular trefoil knot by folding and closing on an octahedral coordination template

Nature Chemistry

Volumn 2, Issue 3, 2010, Pages 218-222

  Guo, Jun ^a,c   Mayers, Paul C ^a   Breault, Gloria A ^b   Hunter, Christopher A ^a  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

^c UNIVERSITY OF GEORGIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77649103938     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.544     Document Type: Article

References (49)

1. Raymo, F. M. & Stoddart, J. F. Interlocked macromolecules. Chem. Rev. 99, 1643-1663 (1999).
2. Breault, G. A., Hunter, C. A. & Mayers, P. C. Supramolecular topology. Tetrahedron 55, 5265-5293 (1999).
3. Chambron, J.-C. et al. Rotaxanes and catenanes built around octahedral transition metals. Eur. J. Org. Chem. 1627-1638 (2004).
4. Schalley, C. A., Reckien, W., Peyerimhoff, S., Baytekin, B. & V̈gtle, F. Theory and experiment in concert: templated synthesis of amide rotaxanes, catenanes, and knots. Chem. Eur. J. 10, 4777-4789 (2004).
5. Vickers, M. S. & Beer, P. D. Anion templated assembly of mechanically interlocked structures. Chem. Soc. Rev. 36, 211-225 (2007).
6. Fenlon, E. E. Open problems in chemical topology. Eur. J. Org. Chem. 30, 5023-5035 (2008).
7. Crowley, J. D., Goldup, S. M., Lee, A.-L., Leigh, D. A. & McBurney, R. T. Active metal template synthesis of rotaxanes, catenanes and molecular shuttles. Chem. Soc. Rev. 38, 1530-1541 (2009).
8. Amabilino, D. B. & Pérez-García, L. Topology in molecules inspired, seen and represented. Chem. Soc. Rev. 38, 1562-1571 (2009).
9. Stoddart, J. F. The chemistry of the mechanical bond. Chem. Soc. Rev. 38, 1802-1820 (2009).
10. Balzani, V., Credi, A., Raymo, F. M. & Stoddart, J. F. Artificial molecular machines. Angew. Chem. Int. Ed. 39, 3348-3391 (2000).
11. Harada, A. Cyclodextrin-based molecular machines. Acc. Chem. Res. 34, 456-464 (2001).
12. Schalley, C. A., Beizai, K. & V̈gtle, F. On the way to rotaxane-based molecular motors: studies in molecular mobility and topological chirality. Acc. Chem. Res. 34, 465-476 (2001).
13. Kay, E. R., Leigh, D. A. & Zerbetto, F. Synthetic molecular motors and mechanical machines. Angew. Chem. Int. Ed. 46, 72-191 (2007).
14. Champin, B., Mobian, P. & Sauvage, J.-P. Transition metal complexes as molecular machine prototypes. Chem. Soc. Rev. 36, 358-366 (2007).
15. Liu, L. F., Depew, R. E. & Wang, J. C. Knotted single-stranded DNA rings: a novel topological isomer of circular single-stranded DNA formed by treatment with Escherichia coli v protein. J. Mol. Biol. 106, 439-452 (1976).
16. Liu, L. F., Perkocha, L., Calender, R. & Wang, J. C. Knotted DNA from bacteriophage capsids. J. Proc. Natl Acad. Sci. USA 78, 5498-5502 (1981).
17. Krasnow, M. A. et al. Determination of the absolute handedness of knots and catenanes of DNA. Nature 304, 559-560 (1983).
18. Liang, C. Z. & Mislow, K. Knots in proteins. J. Am. Chem. Soc. 116, 11189-11190 (1994).
19. Takusagawa, F. & Kamitori, S. A real knot in protein. J. Am. Chem. Soc. 118, 8945-8946 (1996).
20. Taylor, W. R. A deeply knotted protein structure and how it might fold. Nature 406, 916-919 (2000).
21. Dietrich-Buchecker, C., Colasson, B. X. & Sauvage, J.-P. Molecular knots. Top. Curr. Chem. 249, 261-283 (2005).
22. Lukin, O. & V̈gtle, F. Knotting and threading of molecules: chemistry and chirality of molecular knots and their assemblies. Angew. Chem. Int. Ed. 44, 1456-1477 (2005).
23. Dietrich-Buchecker, C. O. & Sauvage, J.-P. A synthetic molecular trefoil knot. Angew. Chem. Int. Ed. Engl. 28, 189-192 (1989).
24. Ashton, P. R. et al. Molecular meccano, 27 - a template-directed synthesis of a molecular trefoil knot. Liebigs Ann. Recueil 2485-2494 (1997).
25. Safarowsky, O., Nieger, M., Fr̈hlich, R. & V̈gtle, F. A molecular knot with twelve amide groups - one-step synthesis, crystal structure, chirality. Angew. Chem. Int. Ed. 39, 1616-1618 (2000).
26. Feigel, M., Ladberg, R., Engels, S., Herbst-Irmer, R. & Fr̈hlich, R. A trefoil knot made of amino acids and steroids. Angew. Chem. Int. Ed. 45, 5698-5720 (2006).
27. Adams, H. et al. Knot tied around an octahedral metal centre. Nature 411, 763 (2003).
28. Chang, S. & Grubbs, R. H. Recent advances in olefin metathesis and its application in organic synthesis. Tetrahedron 54, 4413-4450 (1998).
29. Armstrong, S. K. Ring closing diene metathesis in organic synthesis. J. Chem. Soc. Perkin Trans. I 371-388 (1998).
30. F̈rstner, A. Olefin metathesis and beyond. Angew. Chem. Int. Ed. 39, 3012-3043 (2000).
31. Felpin, F.-X. & Lebreton, J. Recent advances in the total synthesis of piperidine and pyrrolidine natural alkaloids with ring-closing metathesis as a key step. Eur. J. Org. Chem. 3693-3712 (2003).
32. Conrad, J. C. & Fogg, D. E. Ruthenium-catalyzed ring-closing metathesis: recent advances, limitations and opportunities. Curr. Org. Chem. 10, 185-202 (2006).
33. Majumdar, K. C., Rahaman, H. & Roy, B. Synthesis of macrocyclic compounds by ring closing metathesis. Curr. Org. Chem. 11, 1339-1365 (2007).
34. Mohr, B., Weck, M., Sauvage, J.-P. & Grubbs, R. H. High-yield synthesis of [2]catenanes by intramolecular ring-closing metathesis. Angew. Chem. Int. Ed. 36, 1308-1310 (1997).
35. Rapenne, G., Dietrich-Buchecker, C. & Sauvage, J.-P. Copper(I)- or iron(II)- templated synthesis of molecular knots containing two tetrahedral or octahedral coordination sites. J. Am. Chem. Soc. 121, 994-1001 (1999).
36. Leigh, D. A., Lusby, P. J., Teat, S. J.,Wilson, A. J. &Wong, J. K. Y. Benzylic imine catenates: readily accessible octahedral analogues of the Sauvage catenates. Angew. Chem. Int. Ed. 40, 1538-1543 (2001).
37. Hamann, C., Kern, J.-M. & Sauvage, J.-P. Zinc(II)-templated synthesis of a [2]- catenane 2,20,60,20 0-terpyridine-incorporating cycle and a 1,10-phenanthrolinecontaining ring. Inorg. Chem. 42, 1877-1883 (2003).
38. Fuller, A.-M. L., Leigh, D. A., Lusby, P. J., Slawin, A. M. Z. & Walker, D. B. Selecting topology and connectivity through metal-directed macrocyclization reactions: a square planar palladium [2]catenate and two noninterlocked isomers. J. Am. Chem. Soc. 127, 12612-12619 (2005).
39. Tsunoda, T., Yamamiya, Y. & Itâ, S. 1,10-(azodicarbonyl) dipiperidinetributylphosphine, a new reagent system for Mitsunobu reaction. Tetrahedr. Lett. 34, 1639-1642 (1993).
40. Carina, R. F., Dietrich-Buchecker, C. & Sauvage, J.-P. J. Am. Chem. Soc. 118, 9110-9116 (1996).
41. Perrin, D. D. Stability Constants of Metal-Ion Complexes. Part B: Organic Ligands (Pergamon, 1979).
42. Ḧgfeldt, E. (ed.) Stability Constants of Metal-Ion Complexes. Part A: Inorganic Ligands (Pergamon, 1982).
43. Albrecht-Gary, A.-M., Saad, Z., Dietrich-Buchecker, C. O. & Sauvage, J.-P. Interlocked macrocyclic ligands: a kinetic catenand effect in copper(I) complexes. J. Am. Chem. Soc. 107, 3205-3209 (1985).
44. Albrecht-Gary, A.-M., Dietrich-Buchecker, C. O., Saad, Z. & Sauvage, J.-P. Topological kinetic effects: complexation of interlocked macrocyclic ligands by cationic species. J. Am. Chem. Soc. 110, 1467-1472 (1988).
45. Meyer, M., Albrecht-Gary, A.-M., Dietrich-Buchecker, C., Sauvage, J.-P. Dicopper(I) trefoil knots: topological and structural effects on the demetalation rates and mechanism. J. Am. Chem. Soc. 119, 4599-4607 (1997).
46. Mohamadi, F. et al. Macromodel - an integrated software system for modeling organic and bioorganic molecules using molecular mechanics. J. Comput. Chem. 11, 440-467 (1990).
47. Sokolov, V. I. Topological ideas in stereochemistry. Russ. Chem. Rev. 42, 452-463 (1973).
48. Rapenne, G., Dietrich-Buchecker, C. & Sauvage, J.-P. Resolution of a molecular trefoil knot. J. Am. Chem. Soc. 118, 10932-10933 (1996).
49. V̈gtle, F. et al. Novel amide-based molecular knots: complete enantiomeric separation, chiroptical properties, and absolute configuration. Angew. Chem. Int. Ed. 40, 2468-2471 (2001).