Molecular knot

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Crystal structure of a molecular trefoil knot with two copper(I) templating ions bound within it reported by Sauvage and coworkers [1]
Crystal structure of a molecular trefoil knot reported by Vögtle and coworkers in the Angew. Chem. Int. Ed., 2000, 1616-1618.

In chemistry, a molecular knot, or knotane, is a mechanically-interlocked molecular architecture that is analogous to a macroscopic knot.[2] A molecular knot in a trefoil knot configuration is chiral, having at least two enantiomers. Examples of naturally formed knotanes are DNA and certain proteins. Lactoferrin has an unusual biochemical reactivity compared to its linear analogue. Other synthetic molecular knots have a distinct globular shape and nanometer sized dimensions that make them potential building blocks in nanotechnology. The first knot was synthesised by Jean-Pierre Sauvage in 1989.[3]

The term knotane was coined by Fritz Vögtle et al. in Angewandte Chemie International Edition in 2000 by analogy with rotaxane and catenane.[4][5] The term, however, has yet to be adopted by IUPAC.

Several synthetic knotanes have been reported.[6][7][8][9][10][11] A pentafoil knot prepared using dinamic covalent chemistry has been reported.[12] Later in 2016, a fully organic pentafoil knot was also reported, including the very first use of a molecular knot to allosterically regulate catalysis.[13] In January 2017 an 819 knot (the tightest knot yet synthesized) was reported by David Leigh's group.[14]

See also[edit]

References[edit]

  1. ^ Albrecht-Gary, A. M.; Meyer, M.; Dietrich-Buchecker, C. O.; Sauvage, J. P.; Guilhem, J.; Pascard, C. (2 September 2010). "Dicopper (I) trefoil knots: Demetallation kinetic studies and molecular structures". Recueil des Travaux Chimiques des Pays-Bas. 112 (6): 427–428. doi:10.1002/recl.19931120622. 
  2. ^ Lukin, Oleg; Vögtle, Fritz (25 February 2005). "Knotting and Threading of Molecules: Chemistry and Chirality of Molecular Knots and Their Assemblies". Angewandte Chemie International Edition. 44 (10): 1456–1477. doi:10.1002/anie.200460312. PMID 15704147. 
  3. ^ Dietrich-Buchecker, Christiane O.; Sauvage, Jean-Pierre (February 1989). "A Synthetic Molecular Trefoil Knot". Angewandte Chemie International Edition in English. 28 (2): 189–192. doi:10.1002/anie.198901891. 
  4. ^ Lukin O, Vögtle F (2005). "Knotting and Threading of Molecules: Chemistry and Chirality of Molecular Knots and Their Assemblies". Angewandte Chemie International Edition. 44 (10): 1456–1477. doi:10.1002/anie.200460312. PMID 15704147. 
  5. ^ Safarowsky O, Nieger M, Fröhlich R, Vögtle F (2000). "A Molecular Knot with Twelve Amide Groups - One-Step Synthesis, Crystal Structure, Chirality". Angewandte Chemie International Edition. 39 (9): 1616–1618. doi:10.1002/(SICI)1521-3773(20000502)39:9<1616::AID-ANIE1616>3.0.CO;2-Y. PMID 10820452. 
  6. ^ Ashton, Peter R.; Matthews, Owen A.; Menzer, Stephan; Raymo, Françisco M.; Spencer, Neil; Stoddart, J. Fraser; Williams, David J. (December 1997). "Molecular Meccano, 27. A Template-directed Synthesis of a Molecular Trefoil Knot". Liebigs Annalen. 1997 (12): 2485–2494. doi:10.1002/jlac.199719971210. 
  7. ^ Rapenne, Gwénaël; Dietrich-Buchecker, and Jean-Pierre Sauvage *, Christiane; Sauvage, Jean-Pierre (February 1999). "Copper(I)- or Iron(II)-Templated Synthesis of Molecular Knots Containing Two Tetrahedral or Octahedral Coordination Sites". Journal of the American Chemical Society. 121 (5): 1002–1015. doi:10.1021/ja982239+. 
  8. ^ Feigel, Martin; Ladberg, Rüdiger; Engels, Simon; Herbst-Irmer, Regine; Fröhlich, Roland (25 August 2006). "A Trefoil Knot Made of Amino Acids and Steroids". Angewandte Chemie International Edition. 45 (34): 5698–5702. doi:10.1002/anie.200601111. 
  9. ^ Guo, Jun; Mayers, Paul C.; Breault, Gloria A.; Hunter, Christopher A. (7 February 2010). "Synthesis of a molecular trefoil knot by folding and closing on an octahedral coordination template". Nature Chemistry. 2 (3): 218–222. doi:10.1038/nchem.544. 
  10. ^ Barran, Perdita E.; Cole, Harriet L.; Goldup, Stephen M.; Leigh, David A.; McGonigal, Paul R.; Symes, Mark D.; Wu, Jhenyi; Zengerle, Michael (16 December 2011). "Active-Metal Template Synthesis of a Molecular Trefoil Knot". Angewandte Chemie International Edition. 50 (51): 12280–12284. doi:10.1002/anie.201105012. 
  11. ^ Carina, Riccardo F.; Dietrich-Buchecker, Christiane; Sauvage, Jean-Pierre (January 1996). "Molecular Composite Knots". Journal of the American Chemical Society. 118 (38): 9110–9116. doi:10.1021/ja961459p. 
  12. ^ Ayme, Jean-François; Beves, Jonathon E.; Leigh, David A.; McBurney, Roy T.; Rissanen, Kari; Schultz, David (6 November 2011). "A synthetic molecular pentafoil knot". Nature Chemistry. 4 (1): 15–20. doi:10.1038/nchem.1193. PMID 22169866. 
  13. ^ Marcos, Vanesa; Stephens, Alexander J.; Jaramillo-Garcia, Javier; Nussbaumer, Alina L.; Woltering, Steffen L.; Valero, Alberto; Lemonnier, Jean-François; Vitorica-Yrezabal, Iñigo J.; Leigh, David A. (2016-06-24). "Allosteric initiation and regulation of catalysis with a molecular knot". Science. 352 (6293): 1555–1559. doi:10.1126/science.aaf3673. ISSN 0036-8075. PMID 27339983. 
  14. ^ Danon, Jonathan J.; Krüger, Anneke; Leigh, David A.; Lemonnier, Jean-François; Stephens, Alexander J.; Vitorica-Yrezabal, Iñigo J.; Woltering, Steffen L. (2017-01-13). "Braiding a molecular knot with eight crossings". Science. 355 (6321): 159–162. doi:10.1126/science.aal1619. ISSN 0036-8075. PMID 28082585.