Skip to main content
SpringerLink
Log in

Interlocked and Knotted Rings in Biology and Chemistry

  • Conference paper
Bioorganic Chemistry Frontiers

Part of the book series: Bioorganic Chemistry Frontiers ((BIOORGANIC,volume 2))

Abstract

Catenanes are chemical entities consisting of two or more interlocked rings. Such systems, as well as knotted molecules, belong to a branch of chemistry which is related to mathematics, molecular biology and graphic art. Many endeavours have been made to build such topologicaly novel compounds. The statistical methods of preparation, although very simple to conceive and to attempt, are of little practical utility. The directed strategy, using the classical reactions of organic synthesis, offers an interesting alternative route to prepare interlocked ring systems. The most recent approaches, utilizing templated reactions either on transition metals or on organic electron donoracceptor pairs are certainly the most efficient ones for making catenanes. For instance, a gram-scale preparation of [3]-catenanes (two peripheral rings separately interlocked to a central cycle) has been achieved using the transition metal template approach. The metal is able to gather and pre-oriente the several fragments to be incorporated into the target molecule. Although knotted forms of DNA are relatively common, no synthetic molecular knot had been obtained until recently. Here again, the success of the synthetic approach relies on the use of transition metals as templating species. Multinuclear double-stranded helices are interesting intermediate compounds which should allow the preparation of molecular knots and catenanes of increasing topological complexity. The first molecular trefoil knot has only been synthesized and fully characterized recently, although theoretical discussions on chemical knots were published over thirty years ago.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 84.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. a) Woodward RB, Fukunaga T, Kelly RC (1964) J Am Chem Soc 86: 3162

    Google Scholar 

  2. Eaton PE (1979) Tetrahedron 35: 2189

    Article  CAS  Google Scholar 

  3. First synthesis of Dodecahedrane: Ternansky RJ, Balogh DW, Paquette LA (1982) J Am Chem Soc 104: 4503

    Google Scholar 

  4. Crystallographic study: Gallucci JC, Doecke CW, Paquette LA (1986) J Am Chem Soc 108: 1343

    Google Scholar 

  5. Chini P, Longoni G, Albano VG, (1976) Adv Organomet Chem 14: 285 and references therein

    Google Scholar 

  6. Deisenhofer J, Epp O, Miki K, Huber R, Michel H (1984) J Mol Biol 180: 385.

    Article  CAS  Google Scholar 

  7. Deisenhofer J, Epp O, Miki K, Huber R, Michel H (1985) 318: 618

    Google Scholar 

  8. Deisenhofer J, Michel H (1989) the EMBO Journal 8: 2149. Hubber R (1989) Angew Chem Int Ed Engl 28: 848

    Google Scholar 

  9. Bain G (1973) In: The methods of construction of Celtic art, Dover, New York

    Google Scholar 

  10. Locher JC (1971) In: The world of MC Escher, HN Abram, New York

    Google Scholar 

  11. Michel F, Weber C (1988) In Noeuds et Entrelacs, Publication of the Institut de Mathematiques, University of Geneva, Switzerland

    Google Scholar 

  12. Conway JH (1970) In: Computational Problems in Abstract Algebra, Pergamon: New York, p 329

    Google Scholar 

  13. Walba DM (1985) Tetrahedron 41: 3161

    Article  CAS  Google Scholar 

  14. Schill G (1971) In: Catenanes, Rotaxanes and Knots, Academic New York

    Google Scholar 

  15. Schill G, In: Catenanes, Rotaxanes and Knots, Academic New York, 1971, p. 1. Frisch HL, Wasserman E (1961) J Am Chem Soc 83: 3790

    Google Scholar 

  16. Frisch HL, Wasserman E (1961) J Am Chem Soc 83: 3789

    Article  CAS  Google Scholar 

  17. Wasserman E (1960) J Am Chem Soc 82: 4433

    Article  CAS  Google Scholar 

  18. Simmons III, HE; Maggio JE (1981) Tetrahedron Lett 22: 287

    Article  CAS  Google Scholar 

  19. Paquette LA, Yazeux M (1981) Tetrahedron Lett 22: 291

    Article  CAS  Google Scholar 

  20. Kuck D, Schuster A (1988) Angew Chem Int Ed Engl 27: 1192

    Article  Google Scholar 

  21. Walba DM, Richard RM, Haltiwanger RC (1982) J Am Chem Soc 104: 3219

    Article  CAS  Google Scholar 

  22. Van Gulick N (1960) In: Theoretical Aspects of the Linked Ring Problem, unpublished work of August

    Google Scholar 

  23. Sokolov VI (1973) Russian Chemical Reviews 42: 452

    Article  Google Scholar 

  24. Fiers W, Sinsheimer RL (1962) J Mol Biol 5: 408, 420 and 424

    Google Scholar 

  25. Cairns J (1963) J Mol Biol 6: 208.

    Article  CAS  Google Scholar 

  26. Dulbecco R, Vogt M (1963) Proc. Natl. Acad Sci U.S.A. 50: 236.

    Google Scholar 

  27. Weil R, Vinograd J (1963) Proc. Natl. Acad Sci U.S.A. 50: 730

    Google Scholar 

  28. Wasserman SA, Cozzarelli NR (1986) Science 232: 951

    Article  CAS  Google Scholar 

  29. Wang JC (1982) Sci Am 247 (1): 84

    Article  Google Scholar 

  30. Watson JD, Crick FHC (1953) Nature (London) 171: 737 and 964

    Google Scholar 

  31. Wang JC (1979) Proc Natl Acad Sci USA 76: 200 and ref 34 and 35

    Google Scholar 

  32. Vinograd J, Lebowitz J, Radloff R, Watson R, Laipis P (1965) Proc Natl Acad Sci USA 53: 1104

    Article  CAS  Google Scholar 

  33. Bauer WR (1978) Annu Rev Biophys Bioeng 7: 287

    Article  CAS  Google Scholar 

  34. Brown PO, Cozzarelli NR (1979) Science 206: 1081.

    Article  CAS  Google Scholar 

  35. Crick FHC (1976) Proc Natl Acad Sci USA 73: 2639.

    Article  CAS  Google Scholar 

  36. Bauer WR, Crick FHC, White JH (1980) Sci Am 243 (1): 100

    CAS  Google Scholar 

  37. Hudson B, Vinograd J (1967) Nature (London) 216: 647.

    Article  CAS  Google Scholar 

  38. Clayton DA, Vinograd J (1967) Nature (London) 216: 652

    Google Scholar 

  39. Radloff R, Bauer W, Vinograd J (1967) Proc Natl Acad Sci U.S.A. 57, 1514.

    Article  CAS  Google Scholar 

  40. Goebel, W.; Helinski, D.R. (1968) Proc Natl Acad Sci U.S.A. 61:1406.

    Google Scholar 

  41. Riou G, Delain E (1969) Proc Natl Acad Sci U.S.A. 62: 210.

    Google Scholar 

  42. Jaenisch R, Levine AJ (1971) Virology 44: 480.

    Article  CAS  Google Scholar 

  43. MacGregor HC, Vlad M (1972) Chromosoma 39: 205.

    Article  CAS  Google Scholar 

  44. Kreuzer KN, Cozzarelli NR (1980) Cell 20: 245

    Article  CAS  Google Scholar 

  45. Liu LF, Depew RE, Wang JC (1976) J Mol Biol 106: 439

    Article  CAS  Google Scholar 

  46. Liu LF, Liu C.-C, Alberts BM (1980) Cell 19: 697

    Article  CAS  Google Scholar 

  47. Wasserman SA, Cozzarelli NR (1985) Proc Natl Acad Sci USA 82: 1079

    Article  CAS  Google Scholar 

  48. Krasnow MA, Stasiak A, Spengler SJ, Dean F, Koller T, Cozzarelli NR (1983) Nature 304: 559

    Article  CAS  Google Scholar 

  49. Griffith JD, Nash HA (1985) Proc Natl Acad Sci USA 82: 3124

    Article  CAS  Google Scholar 

  50. Wang JC (1971) J Mol Biol 55: 523

    Article  CAS  Google Scholar 

  51. Gellert M, Mizuuchi K, O’Dea MH, Nash HA (1976) Proc Natl Acad Sci USA 73: 3872

    Article  CAS  Google Scholar 

  52. Yang L, Wold MS, Li JJ, Kelly TJ, Liu LF (1987) Proc Natl Acad Sci USA 84: 950

    Article  CAS  Google Scholar 

  53. In Refs. (10 and 11) it is related that “Professor R Willstater discussed interlocked rings in a seminar in Zurich prior to 1912” (V Prelog, “relata refero”)

    Google Scholar 

  54. Agam G, Graiver D, Zilkha A (1976) J Am Chem Soc 98: 5206 Agam G, Zilkha A (1976) ibid 98: 5214

    Google Scholar 

  55. Schill G, Schweickert N, Fritz H, Vetter W (1983) Angew Chem Int Ed Engl 22: 889

    Article  Google Scholar 

  56. Luttringhaus A, Cramer F, Prinzbach H, Henglein FM (1958) Liebigs Ann Chem 613: 185

    Article  CAS  Google Scholar 

  57. Ogino H (1981) J Am Chem Soc 103: 1303. Ogino H, Ohata K (1984) Inorg Chem 23: 3312

    Google Scholar 

  58. Yamanari K, Shimura Y (1983) Bull Chem Soc Jpn 56: 2283

    Article  CAS  Google Scholar 

  59. Wasserman E, Ben-Efraim DA, Wolovsky R (1968) J Am Chem Soc 90: 3286.

    Article  CAS  Google Scholar 

  60. Wolovsky RJ (1970) J Am Chem Soc 92: 2132.

    Google Scholar 

  61. Ben-Efraim DA, Batich C, Wasserman E (1970) J Am Chem Soc 92: 2133

    Google Scholar 

  62. Schill G, Luttringhaus A (1964) Angew Chem 76: 567. Schill G (1967) Chem Ber 100: 2021

    Google Scholar 

  63. Schill G, Zollenkopf H (1969) Liebigs Ann Chem 721: 53

    Article  CAS  Google Scholar 

  64. Schill G (1971) In: Catenanes Rotaxanes and Knots, Academic, New York p 115. Schill G, Ziircher C (1971) Naturwissenschaften 58: 40

    Google Scholar 

  65. See footnote p. 3790 of ref 11

    Google Scholar 

  66. Melson GA (ed) (1979) Coordination chemistry of macrocyclic compounds, Plenum, New York, and references cited therein

    Google Scholar 

  67. Reppe W, Schlichting O, Klager K, Toepel T (1948) Liebigs Ann Chem 560: 1

    Article  CAS  Google Scholar 

  68. Lever ABP (1965) Adv Inorg Radiochem 7: 28

    Google Scholar 

  69. Curtis NF (1960) J Chem Soc 4409. Curtis NF, House DA (1961) Chem Ind (London) 1708

    Google Scholar 

  70. Busch DH (1967) Helv Chim Acta Fasciculus Extraordinarius Alfred Werner 174 and references therein

    Google Scholar 

  71. Boston DR, Rose NJ (1968) J Am Chem Soc 90: 6859

    Article  CAS  Google Scholar 

  72. Parks JE, Wagner BE, Holm RH (1970) J Am Chem Soc 92: 3500. Parks JE, Wagner BE, Holm RH (1971) Inorg Chem 10: 2472

    Google Scholar 

  73. Creaser II, Harrowfield J MacB, Herlt AJ, Sargeson AM, Springborg J, Geue RJ, Snow MR (1977) J Am Chem Soc 99: 3181.

    Article  CAS  Google Scholar 

  74. Creaser II, Geue RJ, Harrowfield JMacB, Herlt AJ, Sargeson AM, Snow MR, Springborg J (1982) J Am Chem Soc 1982 104: 6016

    Article  CAS  Google Scholar 

  75. McMurry TJ, Rodgers SJ, Raymond KN (1987) J Am Chem Soc 109: 345

    Google Scholar 

  76. Belser P, De Cola L, Von Zelewsky A (1988) J Chem Soc Chem Commun 1057

    Google Scholar 

  77. Grammenudi S, Vogtle F (1986) Angew Chem Int Ed Engl 25: 1122

    Article  Google Scholar 

  78. a) Dietrich-Buchecker CO, Marnot PA, Sauvage J.-P, Kirchhoff JR, McMillin DR (1983) J Chem Soc Chem Commun 513.

    Google Scholar 

  79. Dietrich-Buchecker CO, Marnot PA, Sauvage J.-P (1982) Tetrahedron Lett 23: 5291

    Article  CAS  Google Scholar 

  80. Dietrich-Buchecker CO, Marnot PA, Sauvage J.-P, Kintzinger J.-P, Maltese P (1984) Nouv J Chim 8: 573

    CAS  Google Scholar 

  81. Dietrich-Buchecker CO, Sauvage J.-P. Kintzinger J.-P (1983) Tetrahedron Lett 24: 5095

    Google Scholar 

  82. Dietrich-Buchecker CO, Sauvage J.-P (1983) Tetrahedron Lett 24: 5091

    Article  CAS  Google Scholar 

  83. Dietrich-Buchecker CO, Sauvage J.-P, Kern J.-M (1984) J Am Chem Soc 106: 3043

    Article  CAS  Google Scholar 

  84. Vetter W, Logemann E, Schill G (1977) Org Mass Spectrom 12: 351 and references cited therein

    Google Scholar 

  85. Cesario M, Dietrich-Buchecker CO, Guilhem J, Pascard C, Sauvage J.-P (1985) J Chem Soc Chem Commun 244

    Google Scholar 

  86. Schill G, Rissler K, Fritz H, Vetter W (1981) Angew Chem Int Ed Engl 20: 187

    Article  Google Scholar 

  87. Schill G, Schweickert N, Fritz H, Vetter W (1983) Angew Chem Int Ed Engl 22: 889

    Article  Google Scholar 

  88. Albrecht-Gary AM, Dietrich-Buchecker CO, Saad Z, Sauvage J.-P, Weiss J (1986) J Chem Soc Chem Commun 1325

    Google Scholar 

  89. Dietrich-Buchecker CO, Sauvage J.-P, Weiss J (1986) Tetrahedron Lett 27: 2257

    Article  CAS  Google Scholar 

  90. Prelog V, Gerlach H (1964) Helv Chim Acta 47: 2228. Gerlach H, Owtschinnikow JA, Prelog V (1964) Helv Chim Acta 47: 2294

    Google Scholar 

  91. Mitchell DK, Sauvage J.-P (1988) Angew Chem Int Ed Engl 27: 930

    Article  Google Scholar 

  92. Case FH (1951) J Org Chem 16: 1541

    Article  CAS  Google Scholar 

  93. Pirkle W, Hoekstra MS (1976) J Am Chem Soc 98: 1832

    Article  CAS  Google Scholar 

  94. Albrecht-Gary A.-M, Saad Z, Dietrich-Buchecker CO, Sauvage J.-P (1985) J Am Chem Soc 107: 3205.

    Article  CAS  Google Scholar 

  95. Albrecht-Gary A.-M, Saad Z, Dietrich-Buchecker CO, Sauvage J.-P, (1988) 110: 1467

    CAS  Google Scholar 

  96. Arnaud-Neu F, Marques E, Schwing M.-J, Dietrich-Buchecker CO, Sauvage J.-P, Weiss J (1988) J Nouv J Chim 12: 15

    CAS  Google Scholar 

  97. Dietrich-Buchecker CO, Sauvage J.-P, Kern J.-M (1989) J Am Chem Soc 111: 7791

    Article  CAS  Google Scholar 

  98. Norden B, Tjerneld F (1976) FEBS Lett 67: 368. Barton JK (1986) Science 233: 727 and references cited therein

    Google Scholar 

  99. Ortholand J.-Y, Slawin AMZ, Spencer N, Stoddart JF, Williams DJ (1989) Angew Chem Int Ed Engl 28: 1394. Aston PR, Goodnow TT, Kaifer AE, Reddington M, Slawin AMZ, Spencer N, Stoddart JF, Vicent C, Williams DJ (1989) Angew Chem Int. Ed Engl 28: 1396

    Google Scholar 

  100. a) Schill G, Murjahn K (1970) Liebigs Ann Chem 740: 18. (b) Schill G, Rissler K, Fritz H, Vetter W (1981) Angew Chem Int. Ed Engl 20: 187

    Google Scholar 

  101. Schill G, Zurcher C (1969) Angew Chem 81: 996. Schill G, ZCircher C (1977) Chem Ber 110: 2046

    Google Scholar 

  102. Sauvage J.-P, Weiss J (1985) J Am Chem Soc 107: 6108

    Article  CAS  Google Scholar 

  103. Guilhem J, Pascard C, Sauvage J-P, Weiss J (1988) J Am Chem Soc 110: 8711

    Article  CAS  Google Scholar 

  104. Dietrich-Buchecker CO, Khemiss A, Sauvage J-P (1986) J Chem Soc Chem Commun 1376

    Google Scholar 

  105. Eglinton G, Galbraith AR (1956) Chem Ind (London) 737. Eglinton G, Galbraith AR (1959) J Chem Soc 889

    Google Scholar 

  106. Sondheimer F, Amiel Y (1957) J Am Chem Soc 79: 5817. Sondheimer F, Amiel Y, Wolovsky R (1957) J Am Chem Soc 79: 6263

    CAS  Google Scholar 

  107. Jarvi ET, Whitlock HW Jr (1980) J Am Chem Soc 102: 657. Miller SP, Whitlock HW Jr (1984) J Am Chem Soc 106: 1492.

    Google Scholar 

  108. O’Krongly D, Denmeade SR, Chiang MY, Breslow R (1985) J Am Chem Soc 107: 5544

    Article  Google Scholar 

  109. Dietrich-Buchecker CO, Guilhem J, Khemiss AK, Kintzinger J-P, Pascard C, Sauvage J-P (1987) Angew Chem Int Ed Engl 26: 661

    Article  Google Scholar 

  110. Colquhoun HM, Stoddart JF, Williams DJ (1986) Angew Chem Int Ed Engl 25: 487 and references therein

    Google Scholar 

  111. Walba DM, Armstrong JD, Perry AE, Richards RM, Homan TC, Haltiwanger RC (1986) Tetrahedron 42: 1883

    Article  CAS  Google Scholar 

  112. Schill G, Tafelmair L (1971) Synthesis 10: 546

    Article  Google Scholar 

  113. Schill G, Doerjer G, Logemann E, Fritz H (1979) Chem Ber 112: 3603. Schill G, Boeckmann J (1974) Tetrahedron 30: 1945

    Google Scholar 

  114. Walba DM (1987) In Graph Theory and Topology in Chemistry, R B King and DH Rouvray ed, Elsevier

    Google Scholar 

  115. Fuhrhop JH, Struckmeier G, Thewalt U (1976) J Am Chem Soc 98: 278

    Article  Google Scholar 

  116. Sheldrick WS, Engel J (1980) J Chem Soc Chem Commun 5

    Google Scholar 

  117. Bonfiglio JV, Bonnett R, Buckley DG, Hamzetash D, Hursthouse MB, Malick KMA, McDonald AF, Trotter (1983) J Tetrahedron 39: 1865

    Article  CAS  Google Scholar 

  118. Van Stein GC, Van der Poel H, Van Koten G (1980) J Chem Soc Chem Commun 1016. Van Stein GC, Van Koten G, Vrieze K, Brevard C, Spek AL (1984) J Am Chem Soc 106: 4486

    Google Scholar 

  119. Van Stein GC, Van Koten G, Passenier H, Steinebach O, Vrieze K (1984) Inorg Chim Acta 89: 79

    Article  Google Scholar 

  120. Lehn J-M, Rigault A, Siegel J, Harrowfield J, Chevrier B, Moras D (1987) Proc Natl Acad Sci USA 84: 2565. Lehn J-M, Rigault A (1988) Angew Chem Int Ed Engl 27: 1095

    Article  Google Scholar 

  121. Constable EC, Drew MGB, Ward MD (1987) J Chem Soc Chem Commun 1600.

    Google Scholar 

  122. Barley M, Constable EC, Corr SA, McQueen RCS, Nutkins JC, Ward MD, Drew MGB (1988) J Chem Soc Dalton Trans 2655

    Google Scholar 

  123. Libman J, Tor Y, Shanzer A (1987) J Am Chem Soc 109: 5880

    Article  CAS  Google Scholar 

  124. Dietrich-Buchecker CO, Sauvage J-P (1989) Angew Chem Int Ed Engl 28: 189

    Article  Google Scholar 

  125. West R, Rochow EG (1953) J Org Chem 18: 1739. McDermott JX, White JF, Whitesides GM (1976) J Am Chem Soc 98: 6529

    Google Scholar 

  126. Curphey TJ, Hoffman EJ, McDonald C (1967) Chem and Ind (London) 1138

    Google Scholar 

  127. Dietrich-Buchecker CO, Guilhem J, Pascard C, Sauvage J-P (1990) Angew Chem Int Ed Engl 29: 1154

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Laboratoire de Chimie Organo-Minérale, UA 422, Institut de Chimie, F-67008, Strasbourg, France

    Christiane O. Dietrich-Buchecker & Jean-Pierre Sauvage

Authors
  1. Christiane O. Dietrich-Buchecker
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jean-Pierre Sauvage
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Département de Chimie, Université de Montréal, Montréal, Quebec, H3C 3J7, Canada

    H. Dugas

Rights and permissions

Reprints and permissions

Copyright information

© 1991 Springer-Verlag Berlin Heidelberg

About this paper

Cite this paper

Dietrich-Buchecker, C.O., Sauvage, JP. (1991). Interlocked and Knotted Rings in Biology and Chemistry. In: Dugas, H. (eds) Bioorganic Chemistry Frontiers. Bioorganic Chemistry Frontiers, vol 2. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-76241-3_6

Download citation

  • DOI: https://doi.org/10.1007/978-3-642-76241-3_6

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-76243-7

  • Online ISBN: 978-3-642-76241-3

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation