Electron-density determination of electrophilic building blocks as model compounds for protease inhibitors

European Journal of Organic Chemistry

Volumn , Issue 17, 2007, Pages 2759-2768

  Grabowsky, Simon ^a   Pfeuffer, Thomas ^b   Chȩcińska, Lilianna ^a   Weber, Manuela ^a   Morgenroth, Wolfgang ^c,d,e   Luger, Peter ^a   Schirmeister, Tanja ^b  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

^b UNIVERSITY OF WÜRZBURG   (Germany)

^c UNIVERSITY OF GÖTTINGEN   (Germany)

^d AARHUS UNIVERSITY   (Denmark)

^e DESY   (Germany)

Author keywords

Aziridine; Charge density; Electron density; Nucleophile; Protease

Indexed keywords

EID: 34250875146     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200601074     Document Type: Article

References (54)

1. T. S. Koritsánszky, P. Coppens, Chem. Rev. 2001, 101, 1583-1627.
2. P. Coppens, Angew. Chem. 2005, 117, 6970-6972.
3. R. F. W. Bader, Atoms in Molecules - A Quantum Theory, Clarendon Press, Oxford, 1995.
4. G. Naray-Szabo, J. Mol. Graphics 1989, 7, 76-81.
5. R. Flaig, T. Koritsánszky, R. Soyka, L. Häming, P. Luger, Angew. Chem. Int. Ed. 2001, 40, 355-359.
6. D. E. Hibbs, C. J. Austin-Woods, J. A. Platts, J. Overgaard, P. Turner, Chem. Eur. J. 2003, 9, 1075-1083.
7. N. E. Ghermani, A. Spasojevic-de Bire, N. Bouhmaida, S. Ouharzoune, J. Bouligand, A. Layre, R. Gref, P. Couvreur, Pharm. Res. 2004, 21, 598-607.
8. A. Wagner, R. Flaig, B. Dittrich, H. Schmidt, T. Koritsánszky, P. Luger, Chem. Eur. J. 2004, 10, 2977-2982.
9. a) J. C. Powers, J. L. Asgian, O. D. Ekici, K. E. James, Chem. Rev. 2002, 102, 4639-4750;
10. b) H.-H. Otto, T. Schirmeister, Chem. Rev. 1999, 97, 133-172.
11. B. M. Dunn, Chem. Rev. 2002, 102, 4431-4458.
12. a) R. Vicik, M. Busemann, C. Gelhaus, N. Stiefl, W. Schmitz, F. Schulz, M. Mladenovic, B. Engels, M. Leippe, K. Baumann, T. Schirmeister, ChemMedChem. 2006, 1, 1126-1141;
13. b) R. Vicik, H. Helten, T. Schirmeister, B. Engels, ChemMedChem. 2006, 1, 1021-1028.
14. T. Schirmeister, A. Klockow, Mini-Rev. Med. Chem. 2003, 3, 585-596.
15. a) E. Martina, N. Stiefl, B. Degel, F. Schulz, A. Breuning, M. Schiller, R. Vicik, K. Baumann, J. Ziebuhr, T. Schirmeister, Bioorg. Med. Chem. Lett. 2005, 15, 5365-5369;
16. b) S. H. Verhelst, M. Bogyo, ChemBioChem 2005, 6, 824-827.
17. S. Ro, S. G. Baeck, B. Lee, J. H. Ok, J. Pept. Res. 1999. 54, 242-248.
18. a) R. Vicik, M. Busemann, K. Baumann, T. Schirmeister, Curr. Top. Med. Chem. 2006, 6, 331-353;
19. b) M. S. Lall, R. P. Jain, J. C. Vederas, Curr. Top. Med. Chem. 2004, 4, 1239-1253.
20. U. Kaeppler, N. Stiefl, M. Schiller, R. Vicik, A. Breuning, W. Schmitz, D. Rupprecht, C. Schmuck, K. Baumann, J. Ziebuhr, T. Schirmeister, J. Med. Chem. 2005, 48, 6832-6842.
21. M. N. Burnett, C. K. Johnson, ORTEP-III, Oak Ridge Thermal Ellipsoid Plot Program for Crystal Structure Illustrations, Oak Ridge National Laboratory Report ORNL-6895, Oak Ridge, Tennessee, USA, 1996;
22. implemented in PLATON: A. L. Spek, Acta Crystallogr., Sect. A 1990, 46, C-34.
23. N. W. Mitzel, J. Riede, C. Kiener, Angew. Chem. 1997, 109, 2299-2300;
24. Angew. Chem. Int. Ed. Engl. 1997, 36, 2215-2216.
25. E. Espinosa, E. Molins, C. Lecomte, Chem. Phys. Lett. 1998, 285, 170-173.
26. E. Keller, SCHAKAL-99, A Fortran Program for the Graphical Representation of Molecular and Solid-State Structure Models, Albert-Ludwigs-Universität Freiburg, 1999.
27. a) J. Solà, A. Riera, X. Verdaguer, M. A. Maestro, J. Am. Chem. Soc. 2005, 127, 13629-13633;
28. b) J. P. Glusker, Acta Crystallogr., Sect. D 1995, 51, 418-427;
29. c) P. M. Takahara, C. A. Frederick, S. J. Lippard, J. Am. Chem. Soc. 1996, 118, 12309-12321.
30. [36].
31. MOLDEN (version 4.4), in: G. Schaftenaar, J. H. Noordik, J. Comput. Aided Mol. Des. 2000, 14, 123-134.
32. a) P. Luger, M. Messerschmidt, S. Scheins, A. Wagner, Acta Crystallogr., Sect. A 2004, 60, 390-396;
33. b) C. L. Klein, E. D. Stevens, Acta Crystallogr., Sect. B 1988, 44, 50-55.
34. R. F. W. Bader, T. S. Slee, D. Cremer, E. Kraka, J. Am. Chem. Soc. 1983, 105, 5061-5068.
35. L. Chȩcińska, S. Mebs, C. B. Hübschle, D. Förster, W. Morgenroth, P. Luger, Org. Biomol. Chem. 2006, 4, 3242-3251.
36. E. Rödel, M. Messerschmidt, B. Dittrich, P. Luger, Org. Biomol. Chem. 2006, 4, 475-481.
37. a) F. L. Hirshfeld, Theor. Chim. Acta 1977, 44, 129;
38. b) M. A. Spackman, P. G. Byrom, Chem. Phys. Lett. 1991, 267, 215-220.
39. C. B. Hübschle, Mollso, in: C. B. Hübschle, P. Luger, J. Appl. Crystallogr. 2006, 39, 901-904.
40. C. Flensburg, S. Larsen, R. F. Stewart, J. Phvs. Chem. 1995, 99, 10130-10141.
41. a) U. Koch, P. L. A. Popelier, J. Phys. Chem. 1995, 99, 9747;
42. b) P. L. A. Popelier, J. Phys. Chem. A 1998, 102, 1873.
43. T Schirmeister, Liebigs Ann./Recueil 1997, 1895-1899.
44. XDS (version 12/2004) in: a) W. Kabsch, J. Appl. Crystallogr. 1988, 21, 916-924;
45. b) W. Kabsch, J. Appl. Crystallogr. 1993, 26, 795-800.
46. a) G. M. Sheldrick, SHELXS-97, Program for Crystal Structure Solution, 1997, University of Göttingen, Germany;
47. b) SHELXL-97, Program for Refinement of Crystal Structures, 1997, University of Göttingen, Germany.
48. N. K. Hansen, P. Coppens, Acta Crystallogr., Sect. A 1978, 34, 909-921.
49. T. Koritsánszky, T. Richter, P. Macchi, A. Volkov, C. Gatti, S. Howard, P. R. Mallinson, L. Farrugia, Z. W. Su, N. K. Hansen, XD, A Computer Program Package for Multipole Refinement and Analysis of Electron Densities from Diffraction Data, Tech. rep., Freie Universität Berlin, 2003.
50. F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, R. Taylor in International Tables for Crystallography, vol. C (Ed.: A. J. C. Wilson), Kluwer Academic Publishers, Dordrecht, Boston, London, 1992, chapter 9.5, pp. 685-706.
51. GAUSSIAN 03, Revision B.04, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, and J. A. Pople, Gaussian, Inc., Pittsburgh, PA, 2003.
52. a) B. Dittrich, C. B. Hübschle, M. Messerschmidt, R. Kalinowski, D. Girnt, P. Luger, Acta Crystallogr, Sect. A 2005, 61, 314-320;
53. b) M. P. Andersson, P. Uvdal, J. Phys. Chem. A 2005, 109, 2937-2941.
54. P. L. A. Popelier, R. G. A. Bone, MORPHY-98, A Topological Analysis Program, University of Manchester, 1998.