Advertisement

Pyridine and Pyridinium-Based Anion Receptors

  • Nathan L. Kilah
  • Paul D. BeerEmail author
Chapter
Part of the Topics in Heterocyclic Chemistry book series (TOPICS, volume 24)

Abstracts

Abstract

Pyridine and pyridinium heterocycles play an important role in anion receptor chemistry. Hydrogen bond arrays are frequently preorganized by the presence of the pyridine nitrogen lone pair of electrons, whilst the positively charged pyridinium group is capable of interacting with anions via a number of polarized noncovalent interactions. This review describes the development of pyridine and pyridinium-based anion receptors, separated into topologically distinct acyclic, macrocyclic, macrobicyclic and interlocked host systems.

Graphical Abstract

Keywords

Anion Pyridine Pyridinium Receptor 

Abbreviations

ADP

Adenosine 5′-diphosphate

Ala

Alanine

AMP

Adenosine 5′-monophosphate

ATP

Adenosine 5′-triphosphate

Boc

tert-Butoxycarbonyl

CD

Circular dichroism

DFT

Density functional theory

FT

Fourier transform

Gln

Glutamate

Gly

Glycine

HEPES

4-(2-Hydroxyethyl)-1-piperazineethanesulfonic acid

IR

Infrared

ITC

Isothermal titration calorimetry

MOPS

3-(N-morpholino)propanesulfonic acid

NMR

Nuclear magnetic resonance

NOESY

Nuclear Overhauser effect spectroscopy

Phe

Phenylalanine

Pic

Picrate

ROESY

Rotational frame nuclear Overhauser effect spectroscopy

TBA

Tetra(n-butyl)ammonium

Trp

Tryptophan

Val

Valine

Notes

Acknowledgments

NLK gratefully acknowledges the Royal Commission for the Exhibition of 1851 for a research fellowship.

References

  1. 1.
    Berg JM, Tymoczko JL, Stryer L (2006) Biochemistry. W. H. Freeman and Co., New YorkGoogle Scholar
  2. 2.
    Berger AL, Randak CO, Ostedgaard LS, Karp PH, Vermeer DW, Welsh MJ (2005) J Biol Chem 280:5221CrossRefGoogle Scholar
  3. 3.
    Pearce JMS (2002) J Neurol Neurosurg Psychiatry 72:412CrossRefGoogle Scholar
  4. 4.
    Moss B (1996) Chem Ind (London):407Google Scholar
  5. 5.
    O'Hara MJ, Burge SR, Grate JW (2009) Anal Chem 81:1068CrossRefGoogle Scholar
  6. 6.
    Rice CR (2006) Coord Chem Rev 250:3190CrossRefGoogle Scholar
  7. 7.
    Bayly SR, Beer PD (2008) Struct Bond 129:45CrossRefGoogle Scholar
  8. 8.
    Hamuro Y, Geib SJ, Hamilton AD (1996) J Am Chem Soc 118:7529CrossRefGoogle Scholar
  9. 9.
    Hunter CA, Purvis DH (1992) Angew Chem Int Ed 31:792CrossRefGoogle Scholar
  10. 10.
    Kavallieratos K, Bertao CM, Crabtree RH (1999) J Org Chem 64:1675CrossRefGoogle Scholar
  11. 11.
    Liao J-H, Chen C-T, Fang J-M (2002) Org Lett 4:561CrossRefGoogle Scholar
  12. 12.
    Xu K-X, Qing G-Y, He Y-B, Qin H-J, Hu L (2007) Supramol Chem 19:403CrossRefGoogle Scholar
  13. 13.
    Duke RM, O'Brien JE, McCabe T, Gunnlaugsson T (2008) Org Biomol Chem 6:4089CrossRefGoogle Scholar
  14. 14.
    Bates GW, Gale PA, Light ME (2007) Chem Commun:2121Google Scholar
  15. 15.
    Zieliński T, Dydio P, Jurczak J (2008) Tetrahedron 64:568CrossRefGoogle Scholar
  16. 16.
    Beer PD, Graydon AR, Johnson AOM, Smith DK (1997) Inorg Chem 36:2112CrossRefGoogle Scholar
  17. 17.
    Otón F, Tárraga A, Espinosa A, Velasco MD, Molina P (2006) Dalton Trans:3685Google Scholar
  18. 18.
    Kyne GM, Light ME, Hursthouse MB, de Mendoza J, Kilburn JD (2001) J Chem Soc Perkin Trans 1:1258CrossRefGoogle Scholar
  19. 19.
    Yang R, Liu W-X, Shen H, Huang H-H, Jiang Y-B (2008) J Phys Chem B 112:5105CrossRefGoogle Scholar
  20. 20.
    Beer PD, Drew MGB, Graydon AR (1996) J Chem Soc Dalton Trans:4129Google Scholar
  21. 21.
    Sun S-S, Lees AJ, Zavalij PY (2003) Inorg Chem 42:3445CrossRefGoogle Scholar
  22. 22.
    Schmuck C, Machon U (2005) Chem Eur J 11:1109CrossRefGoogle Scholar
  23. 23.
    Ranganathan D, Haridas V, Karle IL (1998) J Am Chem Soc 120:2695CrossRefGoogle Scholar
  24. 24.
    Szumna A, Jurczak J (2001) Eur J Org Chem:4031Google Scholar
  25. 25.
    Szumna A, Jurczak J (2001) Helv Chim Acta 84:3760CrossRefGoogle Scholar
  26. 26.
    Chmielewski M, Jurczak J (2004) Tetrahedron Lett 45:6007CrossRefGoogle Scholar
  27. 27.
    Chmielewski MJ, Szumna A, Jurczak J (2004) Tetrahedron Lett 45:8699CrossRefGoogle Scholar
  28. 28.
    Chmielewski MJ, Jurczak J (2005) Tetrahedron Lett 46:3085CrossRefGoogle Scholar
  29. 29.
    Chmielewski MJ, Jurczak J (2005) Chem Eur J 11:6080CrossRefGoogle Scholar
  30. 30.
    Huang H, Mu L, He J, Cheng J-P (2002) Tetrahedron Lett 43:2255CrossRefGoogle Scholar
  31. 31.
    Zhang Y, Yin Z, He J, Cheng J-P (2007) Tetrahedron Lett 48:6039CrossRefGoogle Scholar
  32. 32.
    Sessler JL, Katayev E, Pantos GD, Ustynyuk YA (2004) Chem Commun:1276Google Scholar
  33. 33.
    Sessler JL, Katayev E, Pantos GD, Scherbakov P, Reshetova MD, Khrustalev VN, Lynch VM, Ustynyuk YA (2005) J Am Chem Soc 127:11442CrossRefGoogle Scholar
  34. 34.
    Katayev EA, Pantos GD, Reshetova MD, Khrustalev VN, Lynch VM, Ustynyuk YA, Sessler JL (2005) Angew Chem Int Ed 44:7386CrossRefGoogle Scholar
  35. 35.
    Katayev EA, Sessler JL, Khrustalev VN, Ustynyuk YA (2007) J Org Chem 72:7244CrossRefGoogle Scholar
  36. 36.
    Brooks SJ, García-Garrido SE, Light ME, Cole PA, Gale PA (2007) Chem Eur J 13:3320CrossRefGoogle Scholar
  37. 37.
    Hossain MA, Kang SO, Powell D, Bowman-James K (2003) Inorg Chem 42:1397CrossRefGoogle Scholar
  38. 38.
    Hossain MA, Kang SO, Llinares JM, Powell D, Bowman-James K (2003) Inorg Chem 42:5043CrossRefGoogle Scholar
  39. 39.
    Kang SO, Day VW, Bowman-James K (2009) Org Lett 11:3654CrossRefGoogle Scholar
  40. 40.
    Kubik S, Goddard R, Kirchner R, Nolting D, Seidel J (2001) Angew Chem Int Ed 40:2648CrossRefGoogle Scholar
  41. 41.
    Kubik S, Goddard R (2002) Proc Natl Acad Sci USA 99:5127Google Scholar
  42. 42.
    Kubik S, Kirchner R, Nolting D, Seidel J (2002) J Am Chem Soc 124:12752CrossRefGoogle Scholar
  43. 43.
    Kubik S, Goddard R, Otto S, Pohl S, Reyheller C, Stüwe S (2005) Biosens Bioelectron 20:2364CrossRefGoogle Scholar
  44. 44.
    Otto S, Kubik S (2003) J Am Chem Soc 125:7804CrossRefGoogle Scholar
  45. 45.
    Reyheller C, Hay BP, Kubik S (2007) New J Chem 31:2095CrossRefGoogle Scholar
  46. 46.
    Reyheller C, Kubik S (2007) Org Lett 9:5271CrossRefGoogle Scholar
  47. 47.
    Li Y, Pink M, Karty JA, Flood AH (2008) J Am Chem Soc 130:17293CrossRefGoogle Scholar
  48. 48.
    Ghosh S, Roehm B, Begum RA, Kut J, Hossain MA, Day VW, Bowman-James K (2007) Inorg Chem 46:9519CrossRefGoogle Scholar
  49. 49.
    Chellappan K, Singh NJ, Hwang I-C, Lee JW, Kim KS (2005) Angew Chem Int Ed 44:2899CrossRefGoogle Scholar
  50. 50.
    Niu H-T, Yin Z, Su D, Niu D, Ao Y, He J, Cheng J-P (2008) Tetrahedron 64:6300CrossRefGoogle Scholar
  51. 51.
    Yuan Y, Gao G, Jiang Z-L, You J-S, Zhou Z-Y, Yuan D-Q, Xie R-G (2002) Tetrahedron 58:8993CrossRefGoogle Scholar
  52. 52.
    Khatri VK, Chahar M, Pavani K, Pandey PS (2007) J Org Chem 72:10224CrossRefGoogle Scholar
  53. 53.
    Sansone F, Baldini L, Casnati A, Lazzarotto M, Ugozzoli F, Ungaro R (2002) Proc Natl Acad Sci USA 99:4842CrossRefGoogle Scholar
  54. 54.
    Bisson AP, Lynch VM, Monahan M-KC, Anslyn EV (1997) Angew Chem Int Ed 36:2340CrossRefGoogle Scholar
  55. 55.
    Niikura K, Bisson AP, Anslyn EV (1999) J Chem Soc Perkin Trans 2:1111Google Scholar
  56. 56.
    Kang SO, Llinares JM, Powell D, VanderVelde D, Bowman-James K (2003) J Am Chem Soc 125:10152CrossRefGoogle Scholar
  57. 57.
    Kang SO, Day VW, Bowman-James K (2010) J Org Chem 75:277CrossRefGoogle Scholar
  58. 58.
    Kang SO, VanderVelde D, Powell D, Bowman-James K (2004) J Am Chem Soc 126:12272CrossRefGoogle Scholar
  59. 59.
    Kang SO, Hossain MA, Powell D, Bowman-James K (2005) Chem Commun:328Google Scholar
  60. 60.
    Kang SO, Powell D, Bowman-James K (2005) J Am Chem Soc 127:13478CrossRefGoogle Scholar
  61. 61.
    Esteban-Gómez D, Platas-Iglesias C, de Blas A, Fabbrizzi L, Rodríguez-Blas T (2008) Chem Eur J 14:5829CrossRefGoogle Scholar
  62. 62.
    Morgan G, McKee V, Nelson J (1995) J Chem Soc Chem Commun:1649Google Scholar
  63. 63.
    McKee V, Morgan GG (2003) Acta Crystallogr Sect C Cryst Struct Commun 59:o150CrossRefGoogle Scholar
  64. 64.
    Farrell D, Gloe K, Gloe K, Goretzki G, McKee V, Nelson J, Nieuwenhuyzen M, Pál I, Stephan H, Town RM, Wichmann K (2003) Dalton Trans:1961Google Scholar
  65. 65.
    Mateus P, Delgado R, Brandão P, Félix V (2009) J Org Chem 74:8638CrossRefGoogle Scholar
  66. 66.
    Jeong K-S, Cho YL (1997) Tetrahedron Lett 38:3279CrossRefGoogle Scholar
  67. 67.
    Amendola V, Boiocchi M, Fabbrizzi L, Palchetti A (2005) Chem Eur J 11:120CrossRefGoogle Scholar
  68. 68.
    Beer PD, Wheeler JW, Grieve A, Moore C, Wear T (1992) J Chem Soc Chem Commun:1225Google Scholar
  69. 69.
    Beer PD, Fletcher NC, Grieve A, Wheeler JW, Moore CP, Wear T (1996) J Chem Soc Perkin Trans 2:1545Google Scholar
  70. 70.
    Beer PD, Fletcher NC, Wear T (1996) Inorg Chim Acta 251:335CrossRefGoogle Scholar
  71. 71.
    Abouderbala LO, Belcher WJ, Boutelle MG, Cragg PJ, Dhaliwal J, Fabre M, Steed JW, Turner DR, Wallace KJ (2002) Chem Commun:358Google Scholar
  72. 72.
    Abouderbala LO, Belcher WJ, Boutelle MG, Cragg PJ, Steed JW, Turner DR, Wallace KJ (2002) Proc Natl Acad Sci USA 99:5001CrossRefGoogle Scholar
  73. 73.
    Turner DR, Paterson MJ, Steed JW (2006) J Org Chem 71:1598CrossRefGoogle Scholar
  74. 74.
    Dickson SJ, Wallace EVB, Swinburne AN, Paterson MJ, Lloyd GO, Beeby A, Belcher WJ, Steed JW (2008) New J Chem 32:786CrossRefGoogle Scholar
  75. 75.
    Swinburne AN, Steed JW (2009) CrystEngComm 11:433CrossRefGoogle Scholar
  76. 76.
    Swinburne AN, Paterson MJ, Fischer KH, Dickson SJ, Wallace EVB, Belcher WJ, Beeby A, Steed JW (2010) Chem Eur J 16:1480CrossRefGoogle Scholar
  77. 77.
    Shinoda S, Tadokoro M, Tsukube H, Arakawa R (1998) Chem Commun:181Google Scholar
  78. 78.
    Atilgan S, Akkaya EU (2004) Tetrahedron Lett 45:9269CrossRefGoogle Scholar
  79. 79.
    Beer PD, Drew MGB, Gradwell K (2000) J Chem Soc Perkin Trans 2:511Google Scholar
  80. 80.
    Tabakci M, Memon S, Yilmaz M, Roundhill DM (2003) J Inclusion Phenom Macrocyclic Chem 45:265CrossRefGoogle Scholar
  81. 81.
    Filby MH, Dickson SJ, Zaccheroni N, Prodi L, Bonacchi S, Montalti M, Paterson MJ, Humphries TD, Chiorboli C, Steed JW (2008) J Am Chem Soc 130:4105CrossRefGoogle Scholar
  82. 82.
    Murakami Y, Ohno T, Hayashida O, Hisaeda Y (1991) J Chem Soc Chem Commun:950Google Scholar
  83. 83.
    Murakami Y, Ohno T, Hayashida O, Hisaeda Y (1991) Chem Lett:1595Google Scholar
  84. 84.
    Murakami Y, Hayashida O, Ito T, Hisaeda Y (1993) Pure Appl Chem 65:551CrossRefGoogle Scholar
  85. 85.
    Murakami Y, Hayashida O, Nagai Y (1994) J Am Chem Soc 116:2611CrossRefGoogle Scholar
  86. 86.
    Hayashida O, Ono K, Hisaeda Y, Murakami Y (1995) Tetrahedron 51:8423CrossRefGoogle Scholar
  87. 87.
    Pflugrath JW, Quiocho FA (1985) Nature 314:257CrossRefGoogle Scholar
  88. 88.
    Luecke H, Quiocho FA (1990) Nature 347:402CrossRefGoogle Scholar
  89. 89.
    He JJ, Quiocho FA (1991) Science 251:1479CrossRefGoogle Scholar
  90. 90.
    Kanyo ZF, Christianson DW (1991) J Biol Chem 266:4264Google Scholar
  91. 91.
    Wisner JA, Beer PD, Drew MGB (2001) Angew Chem Int Ed 40:3606CrossRefGoogle Scholar
  92. 92.
    Wisner JA, Beer PD, Berry NG, Tomapatanaget B (2002) Proc Natl Acad Sci USA 99:4983CrossRefGoogle Scholar
  93. 93.
    Wisner JA, Beer PD, Drew MGB, Sambrook MR (2002) J Am Chem Soc 124:12469CrossRefGoogle Scholar
  94. 94.
    Sambrook MR, Beer PD, Lankshear MD, Ludlow RF, Wisner JA (2006) Org Biomol Chem 4:1529CrossRefGoogle Scholar
  95. 95.
    Curiel D, Beer PD (2005) Chem Commun:1909Google Scholar
  96. 96.
    Hancock LM, Beer PD (2009) Chem Eur J 15:42CrossRefGoogle Scholar
  97. 97.
    Bayly SR, Gray TM, Chmielewski MJ, Davis JJ, Beer PD (2007) Chem Commun:2234Google Scholar
  98. 98.
    Brown A, Mullen KM, Ryu J, Chmielewski MJ, Santos SM, Félix V, Thompson AL, Warren JE, Pascu SI, Beer PD (2009) J Am Chem Soc 131:4937CrossRefGoogle Scholar
  99. 99.
    Lin T-C, Lai C-C, Chiu S-H (2009) Org Lett 11:613CrossRefGoogle Scholar
  100. 100.
    Sambrook MR, Beer PD, Wisner JA, Paul RL, Cowley AR (2004) J Am Chem Soc 126:15364CrossRefGoogle Scholar
  101. 101.
    Ng K-Y, Cowley AR, Beer PD (2006) Chem Commun:3676Google Scholar
  102. 102.
    Huang B, Santos SM, Félix V, Beer PD (2008) Chem Commun:4610Google Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2010

Authors and Affiliations

  1. 1.Department of Chemistry, Inorganic Chemistry LaboratoryUniversity of OxfordOxfordUK

Personalised recommendations