Structure-based drug design: Exploring the proper filling of apolar pockets at enzyme active sites

Journal of Organic Chemistry

Volumn 73, Issue 12, 2008, Pages 4345-4361

  Zürcher, Martina ^a   Diederich, François ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; ARCHITECTURAL DESIGN; BINDING ENERGY; BIOCHEMICAL ENGINEERING; BIOCHEMISTRY; CHEMICAL WATER TREATMENT; CHEMOTHERAPY; COAGULATION; COMPUTER NETWORKS; DRUG DELIVERY; DRUG DOSAGE; DRUG THERAPY; EMPLOYMENT; ENZYME ACTIVITY; ENZYMES; FLOCCULATION; FLOW INTERACTIONS; FLUORINE; FOOD ADDITIVES; HEALTH; INDUSTRIAL ECONOMICS; METROPOLITAN AREA NETWORKS; NETWORK PROTOCOLS; POSITIVE IONS; TARGETS;

ACTIVE SITES; AMERICAN CHEMICAL SOCIETY (ACS); BINDING ACTIVITIES; BINDING AFFINITIES; BLOOD COAGULATION; CASCADE (CO); CATECHOL (CC); CAVITY FILLING; CONFORMATIONAL PREORGANIZATION; DESIGN APPROACHES; ENZYME ACTIVE SITES; ENZYME INHIBITORS; FACTOR XA; FREE ENTHALPY; GUANINE (G); HOST GUEST SYSTEMS; ISOPRENOID BIOSYNTHESIS; MEDICINAL CHEMISTRY; NON-MEVALONATE PATHWAY; O METHYLTRANSFERASE; PARKINSON'S DISEASE (PD); PLASMEPSIN II (PM II); SERINE PROTEASES; STRUCTURE BASED DRUG DESIGN (SBDD); THROMBIN INHIBITORS; WATER NETWORKS;

BINDING SITES;

BLOOD CLOTTING FACTOR 10A; CATECHOL METHYLTRANSFERASE; ENZYME INHIBITOR; GLYCOSYLTRANSFERASE; ISOPRENOID; THROMBIN INHIBITOR; TRANSFER RNA;

BINDING AFFINITY; BIOSYNTHESIS; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; CRYSTALLOGRAPHY; DRUG DESIGN; ENTHALPY; ENZYME ACTIVE SITE; HYDROPHOBICITY; MOLECULAR INTERACTION; REVIEW;

BINDING SITES; DRUG DESIGN; ENZYMES; MODELS, MOLECULAR; MOLECULAR STRUCTURE;

EID: 45249108005     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800527n     Document Type: Review

References (135)

1. (a) Klebe, G. J. Mol. Med. 2000, 78, 269-281.
2. (b) Craig, S. P., III; Eakin, A. E. Vitam. Horm. 2000, 58, 149-169.
3. (c) Anderson, A. C. Chem. Biol. 2003, 10, 787-797.
4. (d) Stahl, M.; Guba, W.; Kansy, M. Drug Discovery Today 2006, 11, 326-333.
5. (a) Böhm, H.-J.; Klebe, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 2588-2614.
6. (b) Babine, R. E.; Bender, S. L. Chem. Rev. 1997, 97, 1359-1472.
7. (c) Hunter, C. A. Angew. Chem., Int. Ed. 2004, 43, 5310-5324.
8. (d) Hobza, P.; Zahradník, R.; Muller-Dethlefs, K. Collect. Czech. Chem. Commun. 2006, 71, 443-531.
9. (a) Diederich, F. Angew. Chem., Int. Ed. Engl. 1988, 27, 362-386.
10. (b) Diederich, F.; Smithrud, D. B.; Sanford, E. M.; Wyman, T. B.; Ferguson, S. B.; Carcanague, D. R.; Chao, I.; Houk, K. N. Acta Chem. Scand. 1992, 46, 205-215.
11. (a) Oshovsky, G. V.; Reinhoudt, D. N.; Verboom, W. Angew. Chem., Int. Ed. 2007, 46, 2366-2393.
12. (b) Hooley, R. J.; Van Anda, H. J.; Rebek, J., Jr. J. Am. Chem. Soc. 2007, 129, 13464-13473.
13. (a) Obst, U.; Gramlich, V.; Diederich, F.; Weber, L.; Banner, D. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 1739-1742.
14. (b) Obst, U.; Banner, D. W.; Weber, L.; Diederich, F. Chem. Biol. 1997, 4, 287-295.
15. Meyer, E. A.; Castellano, R. K.; Diederich, F. Angew. Chem., Int. Ed. 2003, 42, 1210-1250.
16. Paulini, R.; Müller, K.; Diederich, F. Angew. Chem., Int. Ed. 2005, 44, 1788-1805.
17. Hirsch, A. K. H.; Fischer, F. R.; Diederich, F. Angew. Chem.. Int. Ed. 2007, 46, 338-352.
18. Gerber, P. R.; Müller, K. J. Comput.-Aided Mol. Design 1995, 9, 251-268.
19. For a recent article addressing proper cavity filling at the thrombin active site, see: Gerlach, C.; Münzel, M.; Baum, B.; Gerber, H.-D.; Craan, T.; Diederich, W. E.; Klebe, G. Angew. Chem., Int. Ed. 2007, 46, 9105-9109.
20. (a) Diederich, F. Cyclophanes; The Royal Society of Chemistry: Cambridge, 1991.
21. (b) Comprehensive Supramolecular Chemistry; Vögtle, F. Ed.; Elsevier-Pergamon: Oxford, 1996; Vol. 2.
22. (c) Schneider, H.-J.; Yatsimirsky, A. Principles and Methods in Supramolecular Chemistry; Wiley: Chichester, 1999.
23. (d) Diederich, F. In Modern Cyclophane Chemistry; Gleiter, R., Hopf, H. Eds; Wiley-VCH: Weinheim, Germany, 2004.
24. (a) Ferguson, S. B.; Seward, E. M.; Diederich, F.; Sanford, E. M.; Chou, A.; Inocencio-Szweda, P.; Knobler, C. B. J. Org. Chem. 1988, 53, 5593-5595.
25. (b) Smithrud, D. B.; Wyman, T. B.; Diederich, F. J. Am. Chem. Soc. 1991, 113, 5420-5426.
26. (c) Peterson, B. R.; Wallimann, P.; Carcanague, D. R.; Diederich, F. Tetrahedron 1995, 51, 401-421.
27. (a) Inoue, Y.; Liu, Y.; Tong, L.-H.; Shen, B.-J.; Jin, D.-S. J. Am. Chem. Soc. 1993, 115, 10637-10644.
28. (b) Dunitz, J. D. Chem. Biol. 1995, 2, 709-712.
29. (a) Benfield, A. P.; Teresk, M. G.; Plake, H. R.; DeLorbe, J. E.; Millspaugh, L. E.; Martin, S. F. Angew. Chem., Int. Ed. 2006, 45, 6830-6835.
30. (b) Krishnamurthy, V. M.; Bohall, B. R.; Semetey, V.; Whitesides, G. M. J. Am. Chem. Soc. 2006, 128, 5802-5812.
31. (a) Cromwell, W. C.; Byström, K.; Eftink, M. R. J. Phys. Chem. 1985, 89, 326-332.
32. (b) For a detailed discussion, see ref 11a, Chapter 7.4.3, pp 254-257.
33. Obst, U.; Betschmann, P.; Lerner, C.; Seiler, P.; Diederich, F.; Gramlich, V.; Weber, L.; Banner, D. W.; Schönholzer, P. Helv. Chim. Acta 2000, 83, 855-909.
34. Fokkens, J.; Klebe, G. Angew. Chem., Int. Ed. 2006, 45, 985-989.
35. Olsen, J. A.; Banner, D. W.; Seiler, P.; Obst Sander, U.; D'Arcy, A.; Stihle, M.; Müller, K.; Diederich, F. Angew. Chem., Int. Ed. 2003, 42, 2507-2511.
36. For reviews on thrombin inhibitors, see: (a) Rewinkel, J. B. M.; Adang, A. E. P. Curr. Pharm. Design 1999, 5 (12), 1043-1075.
37. (b) Srivastava, S.; Goswami, L. N.; Dikshit, D. K. Med. Res. Rev. 2005, 25, 66-92.
38. (c) Di Nisio, M.; Middeldorp, S.; Büller, H. R. N. Engl. J. Med. 2005, 353, 1028-1040.
39. (d) Schwienhorst, A. Cell. Mol. Life Sci. 2006, 63, 2773-2791.
40. (a) Tucker, T. J.; Brady, S. F.; Lumma, W. C.; Lewis, S. D.; Gardell, S. J.; Naylor-Olsen, A. M.; Yan, Y.; Sisko, J. T.; Stauffer, K. J.; Lucas, B. J.; Lynch, J. J.; Cook, J. J.; Stranieri, M. T.; Holahan, M. A.; Lyle, E. A.; Baskin, E. P.; Chen, I-W.; Dancheck, K. B.; Krueger, J. A.; Cooper, C. M.; Vacca, J. P. J. Med. Chem. 1998, 41, 3210-3219.
41. (b) Zhang, M.; Bailey, D. L.; Bastian, J. A.; Briggs, S. L.; Chirgadze, N. Y.; Clawson, D. K.; Denney, M. L.; Gifford-Moore, D. S.; Harper, R. W.; Johnson, L. M.; Klimkowski, V. J.; Kohn, T. J.; Lin, H.-S.; McCowan, J. R.; Richett, M. E.; Sall, D. J.; Smith, A. J.; Smith, G. F.; Snyder, D. W.; Takeuchi, K.; Utterback, B. G.; Yan, S.-C. B. Bioorg. Med. Chem. Lett. 1999, 9, 775-780.
42. (c) Baettig, U.; Brown, L.; Brundish, D.; Dell, C.; Furzer, A.; Garman, S.; Janus, D.; Kane, P. D.; Smith, G.; Walker, C. V.; Cockcroft, X.; Ambler, J.; Mitchelson, A.; Talbot, M. D.; Tweed, M.; Wills, N. Bioorg. Med. Chem. Lett. 2000, 10, 1563-1566.
43. (a) Betschmann, P.; Lemer, C.; Sahli, S.; Obst, U.; Diederich, F. Chimia 2000, 54, 633-639.
44. (b) Betschmann, P.; Sahli, S.; Diederich, F.; Obst, U.; Gramlich, V. Helv. Chim. Acta 2002, 85, 1210-1245.
45. (c) Schweizer, E. ETH Dissertation No. 16531, Zürich, 2006.
46. (a) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881-1886.
47. (b) For another recent review on fluorine in medicinal chemistry, see Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320-330.
48. (a) Olsen, J.; Seiler, P.; Wagner, B.; Fischer, H.; Tschopp, T.; Obst-Sander, U.; Banner, D. W.; Kansy, M.; Müller, K.; Diederich, F. Org. Biomol. Chem. 2004, 2, 1339-1352.
49. (b) Schweizer, E.; Hoffmann-Röder, A.; Schärer, K.; Olsen, J. A.; Fäh, C.; Seiler, P.; Obst-Sander, U.; Wagner, B.; Kansy, M.; Diederich, F. ChemMedChem 2006, 1, 611-621.
50. For a review on tuning amine basicities, see: Morgenthaler, M.; Schweizer, E.; Hoffmann-Röder, A.; Benini, F.; Martin, R. E.; Jaeschke, G.; Wagner, B.; Fischer, H.; Bendels, S.; Zimmerli, D.; Schneider, J.; Diederich, F.; Kansy, M.; Müller, K. ChemMedChem 2007, 2, 1100-1115.
51. Tucker, T. J.; Lumma, W. C.; Lewis, S. D.; Gardell, S. J.; Lucas, B. J.; Sisko, J. T.; Lynch, J. J.; Lyle, E. A.; Baskin, E. P.; Woltmann, R. F.; Appleby, S. D.; Chen, I-W.; Dancheck, K. B.; Naylor-Olsen, A. M.; Krueger, J. A.; Cooper, C. M.; Vacca, J. P. J. Med. Chem. 1997, 40, 3687-3693.
52. Gerlach, C.; Smolinski, M.; Steuber, H.; Sotriffer, C. A.; Heine, A.; Hangauer, D. G.; Klebe, G. Angew. Chem., Int. Ed. 2007, 46, 8511-8514.
53. (a) Sinnokrot, M. O.; Sherrill, C. D. J. Am. Chem. Soc. 2004, 126, 7690-7697.
54. (b) Lee, E. C.; Hong, B. H.; Lee, I. Y.; Kim, J. C.; Kim, D.; Kim, Y.; Tarakeshwar, P.; Kim, K. S. J. Am. Chem. Soc. 2005, 127, 4530-4537.
55. (c) Ringer, A. L.; Sinnokrot, M. O.; Lively, R. P.; Sherrill, C. D. Chem. Eur. J. 2006, 12, 3821-3828.
56. (a) Tsuzuki, S.; Honda, K.; Uchimaru, T.; Mikami, M.; Fujii, A. J. Phys. Chem. A 2006, 110, 10163-10168.
57. (b) Shibasaki, K.; Fujii, A.; Mikami, N.; Tsuzuki, S. J. Phys. Chem. A 2007, 111, 753-758.
58. Olsen, J. A.; Banner, D. W.; Seiler, P.; Wagner, B.; Tschopp, T.; Obst-Sander, U.; Kansy, M.; Müller, K.; Diederich, F. ChemBioChem 2004, 5, 666-675.
59. CSD search: CSD version 5.29, November 2007, inclusive updates January 2008, containing about 440,000 entries. All searches were performed for structures with R factor <0.1 (not distorted, no error, no partial disorder), excluding polymeric, powder, or organometallic compounds.
60. Schweizer, E.; Hoffmann-Röder, A.; Olsen, J. A.; Seiler, P.; Obst-Sander, U.; Wagner, B.; Kansy, M.; Banner, D. W.; Diederich, F. Org. Biomol. Chem. 2006, 4, 2364-2375.
61. Cockroft, S. L.; Hunter, C. A. Chem. Soc. Rev. 2007, 36, 172-188.
62. Bhayana, B.; Wilcox, C. S. Angew. Chem., Int. Ed. 2007, 46, 6833-6836.
63. (a) Hof, F.; Scofield, D. M.; Schweizer, W. B.; Diederich, F. Angew. Chem., Int. Ed. 2004, 43, 5056-5059.
64. (b) Fischer, F. R.; Schweizer, W. B.; Diederich, F. Angew. Chem., Int. Ed. 2007, 46, 8270-8273.
65. Hoffmann-Röder, A.; Schweizer, E.; Egger, J.; Seiler, P.; Obst-Sander, U.; Wagner, B.; Kansy, M.; Banner, D. W.; Diederich, F. ChemMedChem 2006, 1, 1205-1215.
66. Spartan '06, Wavefunction, Inc.: Irvine, 2006.
67. Bondi, A. J. Phys. Chem. 1964, 68, 441-451.
68. Stauffer, D. A.; Dougherty, D. A. Tetrahedron Lett. 1988, 29, 6039-6042.
69. (a) Dougherty, D. A.; Stauffer, D. A. Science 1990, 250, 1558-1560.
70. (b) Dougherty, D. A. Science 1996, 271, 163-168.
71. (c) Ma, J. C.; Dougherty, D. A. Chem. Rev. 1997, 97, 1303-1324.
72. (d) Zacharias, N.; Dougherty, D. A. Trends Pharmacol. Sci. 2002, 23, 281-287.
73. (e) Dougherty, D. A. J. Nutr. 2007, 137, 1504S-1508S.
74. (f) Hughes, R. M.; Benshoff, M. L.; Waters, M. L. Chem. Eur. J. 2007, 13, 5753-5764.
75. Schärer, K.; Morgenthaler, M.; Paulini, R.; Obst-Sander, U.; Banner, D. W.; Schlatter, D.; Benz, J.; Stihle, M.; Diederich, F. Angew. Chem., Int. Ed. 2005, 44, 4400-4404.
76. (a) Davie, E. W.; Fujikawa, K.; Kisiel, W. Biochemistry 1991, 30, 10363-10370.
77. (b) Maignan, S.; Mikol, V. Curr. Top. Med. Chem. 2001, 1, 161-174.
78. (a) For Rivaroxaban (BAY 59-7939), an oral direct factor Xa inhibitor in phase III clinical trials, see: Agnelli, G.; Gallus, A.; Goldhaber, S. Z.; Haas, S.; Huisman, M. V.; Hull, R. D.; Kakkar, A. K.; Misselwitz, F.; Schellong, S. Circulation 2007, 116, 180-187.
79. (b) For a general recent review on factor Xa inhibitors, see: Ieko, M.; Tarumi, T.; Nakabayashi, T.; Yoshida, M.; Naito, S.; Koike, T. Front. Biosci. 2006, 11, 232-248.
80. (a) Molinoff, P. B.; Axelrod, J. Annu. Rev. Biochem. 1971, 40, 465-500.
81. (b) Guldberg, H. C.; Marsden, C. A. Pharmacol. Rev. 1975, 27, 135-206.
82. Keating, G. M.; Lyseng-Williamson, K. A. CNS Drugs 2005, 19 (2), 165-184.
83. Borgulya, J.; Bruderer, H.; Bernauer, K.; Zürcher, G.; Da Prada, M. Helv. Chim. Acta 1989, 72, 952-968.
84. (a) Masjost, B.; Ballmer, P.; Borroni, E.; Zürcher, G.; Winkler, F. K.; Jakob-Roetne, R.; Diederich, F. Chem. Eur. J. 2000, 6, 971-982.
85. (b) Lerner, C.; Ruf, A.; Gramlich, V.; Masjost, B.; Zürcher, G.; Jakob-Roetne, R.; Borroni, E.; Diederich, F. Angew. Chem., Int. Ed. 2001, 40, 4040-4042.
86. Lerner, C.; Masjost, B.; Ruf, A.; Gramlich, V.; Jakob-Roetne, R.; Zürcher, G.; Borroni, E.; Diederich, F. Org. Biomol. Chem. 2003, 1, 42-49.
87. (a) Paulini, R.; Lerner, C.; Jakob-Roetne, R.; Zürcher, G.; Borroni, E.; Diederich, F. ChemBioChem 2004, 5, 1270-1274.
88. (b) Paulini, R.; Lerner, C.; Diederich, F.; Jakob-Roetne, R.; Zürcher, G.; Borroni, E. Helv. Chim. Acta 2006, 89, 1856-1887.
89. (a) Bonifacio, M. J.; Archer, M.; Rodrigues, M. L.; Matias, P. M.; Learmonth, D. A.; Carrondo, M. A.; Soares-da-Silva, P. Mol. Pharmacol. 2002, 62, 795-805.
90. (b) Tervo, A. J.; Nyrönen, T. H.; Rönkkö, T.; Poso, A. J. Comput.-Aided Mol. Des. 2003, 17, 797-810.
91. (a) Rohmer, M.; Knani, M.; Simonin, P.; Sutter, B.; Sahm, H. Biochem. J. 1993, 295, 517-524.
92. (b) Schwarz, M. K. ETH Dissertation No. 10951, Zürich, 1994.
93. (c) Eisenreich, W.; Schwarz, M.; Cartayrade, A.; Arigoni, D.; Zenk, M. H.; Bacher, A. Chem. Biol. 1998, 5, R221-R233.
94. Jomaa, H.; Wiesner, J.; Sanderbrand, S.; Altincicek, B.; Weidemeyer, C.; Hintz, M.; Türbachova, I.; Eberl, M.; Zeidler, J.; Lichtenthaler, H. K.; Soldati, D.; Beck, E. Science 1999, 285, 1573-1576.
95. Hunter, W. N. J. Biol. Chem. 2007, 282, 21573-21577.
96. (a) Kemp, L. E.; Bond, C. S.; Hunter, W. N. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 6591-6596.
97. (b) Steinbacher, S.; Kaiser, J.; Wungsintaweekul, J.; Hecht, S.; Eisenreich, W.; Gerhardt, S.; Bacher, A.; Rohdich, F. J. Mol. Biol. 2002, 316, 79-88, To date, 10 crystal structures of IspF have been published.
98. Crane, C. M.; Kaiser, J.; Ramsden, N. L.; Lauw, S.; Rohdich, F.; Eisenreich, W.; Hunter, W. N.; Bacher, A.; Diederich, F. Angew. Chem., Int. Ed. 2006, 45, 1069-1074.
99. Baumgartner, C.; Eberle, C.; Diederich, F.; Lauw, S.; Rohdich, F.; Eisenreich, W.; Bacher, A. Helv. Chim. Acta 2007, 90, 1043-1068.
100. Hirsch, A. K. H.; Lauw, S.; Gersbach, P.; Schweizer, W. B.; Rohdich, F.; Eisenreich, W.; Bacher, A.; Diederich, F. ChemMedChem 2007, 2, 806-810.
101. (a) Wada, T.; Kuzuyama, T.; Satoh, S.; Kuramitsu, S.; Yokoyama, S.; Unzai, S.; Tame, J. R. H.; Park, S.-Y. J. Biol. Chem. 2003, 278, 30022-30027.
102. (b) Miallau, L.; Alphey, M. S.; Kemp, L. E.; Leonard, G. A.; McSweeney, S. M.; Hecht, S.; Bacher, A.; Eisenreich, W.; Rohdich, F.; Hunter, W. N. Proc. Natl. Acad. Sci. U.S.A. 2003, 100, 9173-9178.
103. (a) Petrov, V.; Petrova, V.; Girichev, G. V.; Oberhammer, H.; Giricheva, N. I.; Ivanov, S. J. Org. Chem. 2006, 71, 2952-2956.
104. S-C interactions.
105. Hirsch, A. K. H.; Alphey, M. S.; Lauw, S.; Seet, M.; Barandun, L.; Rohdich, F.; Hunter, W. N.; Bacher, A.; Diederich, F. Org. Biomol. Chem. 2008, . submitted. PDB code of the crystal structure: 2VF3.
106. We observed the turning away of larger substituents in cocrystal structures: Crane, C. M.; Hirsch, A. K. H.; Alphey, M. S.; Sgraja, T.; Lauw, S.; Illarionova, V.; Rohdich, F.; Eisenreich, W.; Hunter, W. N.; Bacher, A.; Diederich, F. ChemMedChem 2008, 3, 91-101.
107. Romier, C.; Meyer, J. E. W.; Suck, D. FEBS Lett. 1997, 416, 93-98.
108. Okada, N.; Sasakawa, C.; Tobe, T.; Yamada, M.; Nagai, S.; Talukder, K. A.; Komatsu, K.; Kanegasaki, S.; Yoshikawa, M. Mol. Microbiol. 1991, 5, 187-195.
109. Romier, C.; Reuter, K.; Suck, D.; Ficner, R. EMBO J. 1996, 15, 2850-2857.
110. Xie, W.; Liu, X.; Huang, R. H. Nat. Struct. Biol. 2003, 10, 781-788.
111. Meyer, E. A.; Furler, M.; Diederich, F.; Brenk, R.; Klebe, G. Helv. Chim. Acta 2004, 87, 1333-1356.
112. Meyer, E. A.; Donati, N.; Guillot, M.; Schweizer, W. B.; Diederich, F.; Stengl, B.; Brenk, R.; Reuter, K.; Klebe, G. Helv. Chim. Acta 2006, 89, 573-597.
113. (a) Brenk, R.; Meyer, E. A.; Reuter, K.; Stubbs, M. T.; Garcia, G. A.; Diederich, F.; Klebe, G. J. Mol. Biol. 2004, 338, 55-75.
114. (b) Stengl, B.; Meyer, E. A.; Heine, A.; Brenk, R.; Diederich, F.; Klebe, G. J. Mol. Biol. 2007, 370, 492-511.
115. Meyer, E. A.; Brenk, R.; Castellano, R. K.; Furler, M.; Klebe, G.; Diederich, F. ChemBioChem 2002, 3, 250-253.
116. Hörtner, S. R.; Ritschel, T.; Stengl, B.; Kramer, C.; Schweizer, W. B.; Wagner, B.; Kansy, M.; Klebe, G.; Diederich, F. Angew. Chem., Int. Ed. 2007, 46, 8266-8269.
117. Stengl, B.; Reuter, K.; Klebe, G. ChemBioChem. 2005, 6, 1926-1939.
118. Barillari, C.; Taylor, J.; Viner, R.; Essex, J. W. J. Am. Chem. Soc. 2007, 129, 2577-2587.
119. (a) Silva, A. M.; Lee, A. Y.; Gulnik, S. V.; Majer, P.; Collins, J.; Bhat, T. N.; Collins, P. J.; Cachau, R. E.; Luker, K. E.; Gluzman, I. Y.; Francis, S. E.; Oksman, A.; Goldberg, D. E.; Erickson, J. W. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 10034-10039.
120. (b) Boss, C.; Richard-Bildstein, S.; Weller, T.; Fischli, W.; Meyer, S.; Binkert, C. Curr. Med. Chem. 2003, 10, 883-907.
121. Liu, J.; Gluzman, I. Y.; Drew, M. E.; Goldberg, D. E. J. Biol. Chem. 2005, 280, 1432-1437.
122. (a) Asojo, O. A.; Gulnik, S. V.; Afonina, E.; Yu, B.; Ellman, J. A.; Haque, T. S.; Silva, A. M. J. Mol. Biol. 2003, 327, 173-181.
123. (b) Clemente, J. C.; Govindasamy, L.; Madabushi, A.; Fisher, S. Z.; Moose, R. E.; Yowell, C. A.; Hidaka, K.; Kimura, T.; Hayashi, Y.; Kiso, Y.; Agbandje-McKenna, M.; Dame, J. B.; Dunn, B. M.; McKenna, R. Acta Crystallogr. Sect. D 2006, 62, 246-252.
124. (a) Prade, L.; Jones, A. F.; Boss, C.; Richard-Bildstein, S.; Meyer, S.; Binkert, C.; Bur, D. J. Biol. Chem. 2005, 280, 23837-23843.
125. (b) Boss, C.; Corminboeuf, O.; Grisostomi, C.; Meyer, S.; Jones, A. F.; Prade, L.; Binkert, C.; Fischli, W.; Weller, T.; Bur, D. ChemMedChem 2006, 1, 1341-1345.
126. Oefner, C.; Binggeli, A.; Breu, V.; Bur, D.; Clozel, J.-P.; D'Arcy, A.; Dorn, A.; Fischli, W.; Grüninger, F.; Güller, R.; Hirth, G.; Märki, H. P.; Mathews, S.; Müller, M.; Ridley, R. G.; Stadler, H.; Vieira, E.; Wilhelm, M.; Winkler, F. K.; Wostl, W. Chem. Biol. 1999, 6, 127-131.
127. Hof, F.; Schütz, A.; Fäh, C.; Meyer, S.; Bur, D.; Liu, J.; Goldberg, D. E.; Diederich, F. Angew. Chem., Int. Ed. 2006, 45, 2138-2141.
128. Zürcher, M.; Gottschalk, T.; Meyer, S.; Bur, D.; Diederich, F. ChemMedChem 2008, 3, 237-240.
129. Mecozzi, S.; Rebek, J., Jr. Chem. Eur. J. 1998, 4, 1016-1022.
130. (a) Hayashida, O.; Sebo, L.; Rebek, J., Jr. J. Org. Chem. 2002, 67, 8291-8298.
131. (b) Scarso, A.; Trembleau, L.; Rebek., J., Jr. Angew. Chem., Int. Ed. 2003, 42, 5499-5502.
132. (c) Scarso, A.; Trembleau, L.; Rebek, J., Jr. J. Am. Chem. Soc. 2004, 126, 13512-13518.
133. (d) Gottschalk, T.; Jaun, B.; Diederich, F. Angew. Chem., Int. Ed. 2007, 46, 260-264.
134. (a) Schramm, M. P.; Rebek, J., Jr. Chem. Eur. J. 2006, 12, 5924-5933.
135. (b) Rebek, J., Jr. Chem. Commun. 2007, 2777-2789.