A synthetic molecular pentafoil knot

Nature Chemistry

Volumn 4, Issue 1, 2012, Pages 15-20

  Ayme, Jean François ^a   Beves, Jonathon E ^a   Leigh, David A ^a   McBurney, Roy T ^a   Rissanen, Kari ^b   Schultz, David ^a  

^a UNIVERSITY OF EDINBURGH   (United Kingdom)

^b UNIVERSITY OF JYVÄSKYLÄ   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; AMINE; CHLORIDE; DNA; IMINE; IRON; LIGAND; PYRIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; MACROMOLECULE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALDEHYDES; AMINES; CHLORIDES; CRYSTALLOGRAPHY, X-RAY; DNA; IMINES; IRON; LIGANDS; MACROMOLECULAR SUBSTANCES; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PYRIDINES;

EID: 83655183062     PISSN: 17554330     EISSN: 17554349     Source Type: Journal    
DOI: 10.1038/nchem.1193     Document Type: Article

References (43)

1. Wasserman, S. A. &Cozzarelli, N. R. Biochemical topology: Applications to DNA recombination and replication. Science 232, 951-960 (1986).
2. Taylor, W. R. A deeply knotted protein structure and how it might fold. Nature 406, 916-919 (2000).
3. Taylor,W. R. &Lin, K. Protein knots: A tangled problem. Nature 421, 25 (2003).
4. Wagner, J. R., Brunzelle, J. S., Forest, K. T. &Vierstra, R. D. A light-sensing knot revealed by the structure of the chromophore-binding domain of phytochrome. Nature 438, 325-331 (2005).
5. Taylor,W. R. Protein knots and fold complexity: Some new twists. Comput. Biol. Chem. 31, 151-162 (2007).
6. Saitta, A. M., Soper, P. D., Wasserman, E. &Klein, M. L. Influence of a knot on the strength of a polymer strand. Nature 399, 46-48 (1999).
7. Arai, Y. et al. Tying a molecular knot with optical tweezers. Nature 399, 446-448 (1999).
8. Menasco, W. W. &Thistlethwaite, M. B. (eds) Handbook of Knot Theory (Elsevier, 2005).
9. Fenlon, E. E. Open problems in chemical topology. Eur. J. Org. Chem. 5023-5035 (2008).
10. Beves, J. E., Blight, B. A., Campbell, C. J., Leigh, D. A. &McBurney, R. T. Strategies and tactics for the metal-directed synthesis of rotaxanes, knots, catenanes, and higher order links. Angew. Chem. Int. Ed. 50, 9260-9327 (2011).
11. Alexander, J. W. &Briggs, G. B. On types of knotted curves. Ann. Math. 28, 562-586 (1926-1927).
12. Adams, C. C. The Knot Book (American Mathematical Society, 2004).
13. Dietrich-Buchecker, C. O. &Sauvage, J.-P. A synthetic molecular trefoil knot. Angew. Chem. Int. Ed. Engl. 28, 189-192 (1989).
14. Piguet, C., Bernardinelli, G. &Hopfgartner, G. Helicates as versatile supramolecular complexes. Chem. Rev. 97, 2005-2062 (1997).
15. Ashton, P. R. et al. Molecular meccano 27. A template-directed synthesis of a molecular trefoil knot. Liebigs Ann. Recueil 2485-2494 (1997).
16. 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).
17. Safarowsky, O., Nieger, M., Fröhlich. R. &Vögtle, F. A molecular knot with twelve amide groups-one-step synthesis, crystal structure, chirality. Angew. Chem. Int. Ed. 39, 1616-1618 (2000).
18. Lukin, O. &Vögtle, F. Knotting and threading of molecules: Chemistry and chirality of molecular knots and their assemblies. Angew. Chem. Int. Ed. 44, 1456-1477 (2005).
19. Feigel, M., Ladberg, R., Engels, S., Herbst-Irmer, R. &Fröhlich, R. A trefoil knot made of amino acids and steroids. Angew. Chem. Int. Ed. 45, 5698-5702 (2006).
20. Fenlon, E. E. &Ito, B. R. The thread &cut method: Syntheses of molecular knot precursors. Eur. J. Org. Chem. 3065-3068 (2008).
21. Guo, J., Mayers, P. C., Breault, G. A. &Hunter, C. A. Synthesis of a molecular trefoil knot by folding and closing on an octahedral coordination template. Nature Chem. 2, 218-222 (2010).
22. Barran, P. E. et al. Active metal template synthesis of a molecular trefoil knot. Angew. Chem. Int. Ed. http://dx.doi.org/10.1002/anie.201105012 (2011).
23. Carina, R. F., Dietrich-Buchecker, C. &Sauvage, J.-P. Molecular composite knots. J. Am. Chem. Soc. 118, 9110-9116 (1996).
24. Fujita, M., Ibukuro, F., Hagihara, H. &Ogura, K. Quantitative self-assembly of a [2]catenane from two preformed molecular rings. Nature 367, 720-723 (1994).
25. Wang, L., Vysotsky, M. O., Bogdan, A., Bolte, M. &Böhmer, V. Multiple catenanes derived from calix[4]arenes. Science 304, 1312-1314 (2004).
26. Lam, R. T. S. et al. Amplification of acetylcholine-binding catenanes from dynamic combinatorial libraries. Science 308, 667-669 (2005).
27. Ronson, T. K. et al. Stellated polyhedral assembly of a topologically complicated Pd4L4 'Solomon cube'. Nature Chem. 1, 212-216 (2009).
28. Hasell, T. et al. Triply interlocked covalent organic cages. Nature Chem. 2, 750-755 (2010).
29. Chichak, K. S. et al. Molecular Borromean rings. Science 304, 1308-1312 (2004).
30. Dietrich-Buchecker, C., Colasson, B., Jouvenot, D. &Sauvage, J.-P. Synthesis of multi-1,10-phenanthroline ligands with 1,3-phenylene linkers and their lithium complexes. Chem. Eur. J. 11, 4374-4386 (2005).
31. Hasenknopf, B., Lehn, J-M., Kneisel, B. O., Baum, G. &Fenske, D. Self-assembly of a circular double helicate. Angew. Chem. Int. Ed. Engl. 35, 1838-1840 (1996).
32. Hasenknopf, B. et al. Self-assembly of tetra- and hexanuclear circular helicates. J. Am. Chem. Soc. 119, 10956-10962 (1997).
33. Hasenknopf, B., Lehn, J-M., Boumediene, N., Leize, E. &Van Dorsselaer, A. Kinetic and thermodynamic control in self-assembly: Sequential formation of linear and circular helicates. Angew. Chem. Int. Ed. 37, 3265-3268 (1998).
34. 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).
35. Hogg, L. et al. A simple general ligand system for assembling octahedral metal-rotaxane complexes. Angew. Chem. Int. Ed. 43, 1218-1221 (2004).
36. Hutin, M., Schalley, C. A., Bernardinelli, G. &Nitschke, J. R. Helicate, macrocycle, or catenate: Dynamic topological control over subcomponent selfassembly. Chem. Eur. J. 12, 4069-4076 (2006).
37. Price, J. R. et al. Copper(I)-templated synthesis of a 2,2'-bipyridine derived [2]catenane: Synthetic, modelling, and X-ray studies. Aust. J. Chem. 62, 1014-1019 (2009).
38. Murcko, M. A. &DiPaola, R. A. Ab initio molecular orbital conformational analysis of prototypical organic systems. 1. Ethylene glycol and 1,2-dimethoxyethane. J. Am. Chem. Soc. 114, 10010-10018 (1992).
39. Ohsawa, Y., DeArmond, M. K., Hanck, K.W. &Moreland, C. G. A proton NMR study of reduced paramagnetic tris(2,2'-bipyridine) complexes of iron(II), ruthenium(II) and osmium(II). J. Am. Chem. Soc. 107, 5383-5386 (1985).
40. Mamula, O., von Zelewsky, A. &Bernardinelli, G. Completely stereospecific self-assembly of a circular helicate. Angew. Chem. Int. Ed. 37, 290-293 (1998).
41. Krämer, R., Lehn, J-M. &Marquis-Rigault, A. Self-recognition in helicate self-assembly: Spontaneous formation of helical metal complexes from mixtures of ligands and metal ions. Proc. Natl Acad. Sci. USA 90, 5394-5398 (1993).
42. Albrecht, M. 'Let's twist again'-double-stranded, triple-stranded, and circular helicates. Chem. Rev. 101, 3457-3497 (2001).
43. Nitschke, J. R. Construction, substitution, and sorting of metallo-organic structures via subcomponent self-assembly. Acc. Chem. Res. 40, 103-112 (2007).