Tailored polymer-supported templates in dynamic combinatorial libraries: Simultaneous selection, amplification and isolation of synthetic receptors

Chemistry - A European Journal

Volumn 14, Issue 29, 2008, Pages 9006-9019

  Besenius, Pol ^a   Cormack, Peter A G ^a   Liu, Jingyuan ^b   Otto, Sijbren ^b   Sanders, Jeremy K M ^b   Sherrington, David C ^a  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

^b UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

Affinity chromatography; Dynamic combinatorial chemistry; Molecular recognition; Polymer supported templates; Synthetic receptors

Indexed keywords

ABS RESINS; AFFINITY CHROMATOGRAPHY; AMPLIFICATION; BIOASSAY; BIOCHIPS; CHROMATOGRAPHIC ANALYSIS; LIBRARIES; LIQUID CHROMATOGRAPHY; MICROARRAYS; MOLECULAR BIOLOGY; MOLECULAR RECOGNITION; OPTICAL DEVICES; PHASE SEPARATION; SEPARATION;

BUILDING BLOCKS; CHROMATOGRAPHIC SEPARATIONS; CINCHONA ALKALOIDS; CONTROLLED SYNTHESES; DIASTEREOSELECTIVE; DYNAMIC COMBINATORIAL LIBRARIES; ENANTIO; MACROCYCLIC RECEPTORS; POLYMER MORPHOLOGIES; POLYMER SUPPORTS; SINGLE STEPS; SUPPORTED TEMPLATES; SYNTHETIC RECEPTORS; SYNTHETIC ROUTES; SYSTEMATIC STUDIES; TEMPLATING;

POLYMERS;

CINCHONA ALKALOID; POLYMER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SURFACE PROPERTY; TRANSMISSION ELECTRON MICROSCOPY;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CINCHONA ALKALOIDS; COMBINATORIAL CHEMISTRY TECHNIQUES; MICROSCOPY, ELECTRON, TRANSMISSION; MOLECULAR STRUCTURE; POLYMERS; SURFACE PROPERTIES;

EID: 55049136453     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200800326     Document Type: Article

References (90)

1. A. Krasinski, Z. Radic, R. Manetsch, J. Raushel, P. Taylor, K. B. Sharpless, H. C. Kolb, J. Am. Chem. Soc. 2005, 127, 6686.
2. H. C. Kolb, K. B. Sharpless, Drug Discovery Today 2003, 8, 1128.
3. O. Ramström, J.-M. Lehn, ChemBioChem 2000, 1, 41.
4. O. Ramström, J.-M. Lehn, Nat. Rev. Drug Discovery 2002, 1, 26.
5. O. Ramström, T. Bunyapaiboonsri, S. Lohmann, J.-M. Lehn, Biochim. Biophys. Acta 2002, 1572, 178.
6. C. Karan, B. L. Miller, Drug Discovery Today 2000, 5, 67.
7. S. J. Rowan, S. J. Cantrill, G. R. L. Cousins, J. K. M. Sanders, J. F. Stoddart, Angew. Chem. 2002, 114, 938;
8. Angew. Chem. Int. Ed. 2002, 41, 898.
9. S. Otto, R. L. E. Furlan, J. K. M. Sanders, Drug Discovery Today 2002, 7, 117.
10. J. K. M. Sanders, Phil. Trans. Roy. Soc. 2004, 362, 1239.
11. S. Otto, R. L. E. Furlan, J. K. M. Sanders, Curr. Op. Chem. Biol. 2002, 6, 321.
12. S. Otto, Curr. Opin. Drug Discovery Dev. 2003, 6, 509.
13. S. Otto, J. K. M. Sanders, in Encyclopedia of Supramolecular Chemistry (Eds.: J. L. Atwood, J. W. Steed), Marcel Dekker, New York, 2004, p. 1427.
14. P. T. Corbett, J. Leclaire, L. Vial, K. R. West, J.-L. Wietor, J. K. M. Sanders, S. Otto, Chem. Rev. 2006, 106, 3652.
15. S. Otto, K. Severin, Top. Curr. Chem. 2007, 277, 267.
16. S. Ladame, Org. Biomol. Chem. 2008, 6, 219.
17. B. Brisig, J. K. M. Sanders, S. Otto, Angew. Chem. 2003, 115, 1308;
18. Angew. Chem. Int. Ed. 2003, 42, 1270.
19. L. Vial, J. K. M. Sanders, S. Otto, New J. Chem. 2005, 29, 1001.
20. A. Buryak, K. Severin, Angew. Chem. 2005, 117, 8149;
21. Angew. Chem. Int. Ed. 2005, 44, 7935.
22. K. R. West, K. Bake, S. Otto, Org. Lett. 2005, 7, 2615.
23. K. R. West, S. Otto, Curr. Drug Discovery Technol. 2005, 2, 123.
24. A. V. Eliseev, M. I. Nelen, J. Am. Chem. Soc. 1997, 119, 1147.
25. A. V. Eliseev, M. I. Nelen, Chem. Eur. J. 1998, 4, 825.
26. H. Hioki, W. C. Still, J. Org. Chem. 1998, 63, 904.
27. B. Klekota, M. H. Hammond, B. L. Miller, Tetrahedron Lett. 1997, 38, 8639.
28. B. Klekota, B. L. Miller, Tetrahedron 1999, 55, 11687.
29. S. L. Roberts, R. L. E. Furlan, O. R. L. Cousins, J. K. M. Sanders, Chem. Commun. 2002, 938.
30. B. R. McNaughton, B. L. Miller, Org. Lett. 2006, 8, 1803.
31. B. R. McNaughton, P. C. Gareiss, B. L. Miller, J. Am. Chem. Soc. 2007, 129, 11306.
32. K. Severin, Chem. Eur. J. 2004, 10, 2565.
33. J. S. Moore, N. W. Zimmerman, Org. Lett. 2000, 2, 915.
34. S. C. Zimmerman, K. W. Saoinz, Z. Zeng, Proc. Natl. Acad. Sci. USA 1993, 90, 1190.
35. S. C. Zimmerman, K. W. Saoinz, J. Am. Chem. Soc. 1995, 117, 1175.
36. M. Kamieth, U. Burkert, P. S. Corbin, S. J. Dell, S. C. Zimmerman, F.-G.. Klärner, Eur. J. Org. Chem. 1999, 2741.
37. S. C. Zimmerman, W.-S. Kwan, Angew. Chem. 1995, 107, 2589;
38. Angew. Chem. Int. Ed. Engl. 1995, 34, 2404.
39. F. Gasparrini, D. Misiti, C. Villani, A. Borchardt, M. T. Burger, W. C. Still, J. Org. Chem. 1995, 60, 4314.
40. F. Gasparrini, D. Misiti, W. C. Still, C. Villani, H. Wennemers, J. Org. Chem. 1997, 62, 8221.
41. A. Bianco, F. Gasparrini, M. Maggini, D. Misiti, A. Polese, M. Prato, G. Scorrano, C. Toniolo, C. Villani, J. Am. Chem. Soc. 1997, 119, 7550.
42. F. Gasparrini, D. Misiti, F. D. Negra, M. Maggini, G. Scorrano, C. Villani, Tetrahedron 2001, 57, 6997.
43. F. Gasparrini, D. Misiti, M. Pierini, C. Villani, Org. Lett. 2002, 4, 3993.
44. R. J. Pieters, J. Cuntze, M. Bonnet, F. Diederich, J. Chem. Soc. Perkin Trans. 2 1997, 1891.
45. L. J. D'Souza, U. Maitra, J. Org. Chem. 1996, 61, 9494.
46. R. L. E. Furlan, Y.-F. Ng, S. Otto, J. K. M. Sanders, J. Am. Chem. Soc. 2001, 123, 8876.
47. S. L. Roberts, R. L. E. Furlan, S. Otto, J. K. M. Sanders, Org. Biomol. Chem. 2003, 1, 1625.
48. R. T. S. Lam, A. Belenguer, S. L. Roberts, C. Neumann, T. Jarrosson, S. Otto, J. K. M. Sanders, Science 2005, 308, 667.
49. J. Liu, K. R. West, C. R. Bondy, J. K. M. Sanders, Org. Biomol. Chem. 2007, 5, 778.
50. F. Bulos, S. L. Roberts, R. L. E. Furlan, J. K. M. Sanders, Chem. Commun. 2007, 3092.
51. J. Liu, R. F. Ludlow, R. L. E. Furlan, S. Otto, J. K. M. Sanders, unpublished results.
52. R. F. Ludlow, J. Liu, H.-X. Li, S. L. Roberts, J. K. M. Sanders, S. Otto, Angew. Chem. 2007, 119, 5864;
53. Angew. Chem. Int. Ed. 2007, 46, 5762.
54. G. R. L. Cousins, R. L. E. Furlan, Y.-F. Ng, J. E. Redman, J. K. M. Sanders, Angew. Chem. 2001, 113, 437;
55. Angew. Chem. Int. Ed. 2001, 40, 423.
56. D. C. Sherrington, Chem. Commun. 1998, 2275.
57. F. S. Macintyre, D. C. Sherrington, Macromolecules 2004, 37, 7628.
58. R. B. Merrifield, J. Am. Chem. Soc. 1963, 85, 2149.
59. S. M. Howdle, K. Jerábek, V. Leocorbo, P. C. Marr, D. C. Sherrington, Polymer 2000, 41, 7273.
60. E. R. Francotte, J. Chromatogr. A 2001, 906, 379.
61. F. Gasparrini, D. Misiti, C. Villani, J. Chromatogr. A 2001, 906, 35.
62. Q.-H. Fan, Y.-M. Li, A. S. C. Chan, Chem. Rev. 2002, 102, 3385.
63. S. V. Ley, I. R. Baxendale, R. N. Bream, P. S. Jackson, A. G. Leach, D. A. Longbottom, M. Nesi, J. S. Scott, R. I. Storer, S. J. Taylor, J. Chem. Soc. Perkin Trans. 1 2000, 3815.
64. D. Obrecht, J. M. Villalgordo, Tetrahedron Organic Chemistry Series, Vol. 17, Solid-Supported Combinatorial and Parallel Synthesis of Small Molecular Weight Compound Libraries, Pergamon, Elsevier, Oxford (UK) 1998.
65. M. R. Buchmeiser, Polymeric Materials in Organic Synthesis and Catalysis, Wiley-VCH, Weinheim, 2003.
66. M. Benaglia, A. Puglisi, F. Cozzi, Chem. Rev. 2003, 103, 3401.
67. C. Bolm, A. Gerlach, Eur. J. Org. Chem. 1998, 21.
68. S. J. Shuttleworth, S. M. Allin, P. K. Sharma, Synthesis 1997, 1217.
69. K. Hermann, H. Wynberg, Helv. Chim. Acta 1977, 60, 2208.
70. B. Thierry, D. Paramelle, J.-C. Plaquevent, D. Cahard, in http://www.mdpi.net, ESCSOC-6 Proceedings, Poster B01, 2002.
71. T. Danelli, R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, G. Tocco, Tetrahedron: Asymmetry 2003, 14, 461.
72. W. Lindner, M. Lämmerhofer, N. M. Maier, 2001, US 6313247.
73. J. Hiratake, M. Inagaki, Y. Yamamoto, J. Oda, J. Chem. Soc. Perkin Trans. 1 1987, 1053.
74. S. J. Rowan, J. K. M. Sanders, J. Org. Chem. 1998, 63, 1536.
75. M. Inagaki, J. Hiratake, Y. Yamamoto, J. Oda, Bull. Chem. Soc. Jpn. 1987, 60, 4121.
76. D. Pini, A. Petri, P. Salvadori, Tetrahedron 1994, 50, 11321.
77. M. Heidelberger, W. A. Jacobs, J. Am. Chem. Soc. 1919, 41, 817.
78. E. J. Corey, J. Zhang, Org. Lett. 2001, 3, 3211.
79. P. G. Williard, C. B. Fryhle, Tetrahedron Lett. 1980, 21, 3731.
80. G. Majetich, Y. Zhang, K. Wheless, Tetrahedron Lett. 1994, 35, 8727.
81. D. C. Sherrington, J. Polym. Sci. Part A: Polym. Chem. 2001, 39, 2364.
82. H. C. Henderson, D. C. Sherrington, Polymer 1994, 35, 2867.
83. J. G. Heffernan, W. M. McKenzie, D. C. Sherrington, J. Chem. Soc. Perkin Trans. 2 1981, 514.
84. W. M. McKenzie, D. C. Sherrington, J. Chem. Soc. Chem. Commun. 1978, 541.
85. D. C. Sherrington, A. Lanver, H.-G. Schmalz, Angew. Chem. 2002, 114, 3808;
86. Angew. Chem. Int. Ed. 2002, 41, 3656.
87. W.-H. Li, H. D. H. Stöver, J. Polym. Sci., Part A: Polym. Chem. 1998, 36, 1543.
88. W.-H. Li, K. Li, H.D.H. Stöver, J. Polym. Sci. Part A: Polym. Chem. 1999, 37, 2295.
89. M. J. T. Morrison, PhD Thesis, Department of Pure & Applied Chemistry, University of Strathclyde (Glasgow), 2000.
90. K. W. Pepper, D. Reichenburg, D. K. J. Hale, J. Chem. Soc. 1952, 4, 3129.