X-ray structures and ab initio study of the conformational properties of novel oxazole and thiazole containing di- and tripeptide mimetics

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 5, 2000, Pages 1081-1085

  Kaiser, Dietmar ^a   Videnov, Georgi ^a   Maichle Mössmer, Cäcilia ^a   Strähle, Joachim ^a   Jung, Günther ^a  

^a UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CHEMICAL BONDS; CONFORMATIONS; CRYSTAL STRUCTURE; MATHEMATICAL MODELS; NUMERICAL ANALYSIS; PROBABILITY DENSITY FUNCTION; X RAY ANALYSIS;

OXAZOLE; THIAZOLE; TRIPEPTIDE MIMETICS;

ORGANIC COMPOUNDS;

EID: 0034191469     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a909842i     Document Type: Article

References (45)

1. (a) G. Hölzemann, Peptide Conformation Mimetics, in Kontakte, (Darmstadt) 1991, pp. 3-12
2. (b) G Hölzemann, in Kontakte, (Darmstadt) 1991, pp. 55-63 and refs. cited therein.
3. G. Videnov, D. Kaiser, C. Kempter and G. Jung, Angew. Chem., 1996, 108, 1604
4. G. Videnov, D. Kaiser, C. Kempter and G. Jung, Angew. Chem., Int. Ed. Engl., 1996, 35, 1503.
5. (a) N. Fusetani and S. Matsunaga, Chem. Rev., 1993, 93, 1793
6. (b) B. S. Davidson, Chem. Rev., 1993, 93, 1771
7. (c) J. Kobayashi and M. Ishibashi, Chem. Rev., 1993, 93, 1753
8. (d) M. J. Garson, Chem. Rev., 1993 93, 1699
9. (e) J. P. Michael and G. Pattenden, Angew. Chem., 1993, 105, 1
10. J. P. Michael and G. Patterden, Angew. Chem., Int. Ed. Engl., 1993, 32, 1
11. (f) G. J. Pattenden, J. Heterocycl. Chem., 1992, 29, 607
12. J. R. Lewis, Nat. Prod. Rep., 1993, 10, 29
13. (h) J. R. Lewis Nat. Prod. Rep., 1992, 9, 81
14. (i) D. J. Faulkner, Nat. Prod. Rep., 1992, 9, 323
15. (j) H. Drechsel, H. Stephan, R. Lotz, H. Haag, H. Zähner, K. Hantke and G. Jung, Liebigs Ann. Chem., 1995, 1727
16. (k) H. G. Floss and J. M. Beale, Angew. Chem., 1989, 101, 147
17. H. G. Floss and J. M. Beale, Angew. Chem., Int. Ed. Engl., 1989, 28, 146
18. (l) B. T. Breil, P W. Ludden and E. W. Triplett, J. Bacteriol., 1993, 175, 3693.
19. (a) A. Bayer, S. Freund, G. N. Nicholson and G. Jung, Angew. Chem., 1993, 105, 1410
20. A. Bayer, S. Freund, G. N. Nicholson and G. Jung, Angew. Chem., Int. Ed. Engl., 1993, 32, 1336
21. (b) A. Bayer, S. Freund and G. Jung, Eur. J. Biochem., 1995, 234, 414.
22. N. Hamamichi, A. Natrajan and S. M. Hecht, J. Am. Chem. Soc., 1992, 114, 6278
23. M. Rubio, M. Merchán and E. Ortí, Theor. Chim. Acta, 1995, 91, 17 and refs. therein.
24. S. G. Cho, Y. G. Cheun and B. S. Park, J. Chem. Soc., Faraday Trans., 1997, 93, 2967.
25. (a) G. Barabarella, M. Zambianchi, L. Antolini, U. Folli, F. Goldoni, D. Iarossi, L. Schenetti and A. Bongini, J. Chem. Soc., Perkin Trans. 2, 1995, 2, 1869
26. (b) V. Hernandez and J. T. L. Navarrette, J. Chem. Phys., 1994, 101, 1369.
27. (a) S. T. Howard, J. Am. Chem. Soc., 1996, 118, 10269
28. (b) J. Cioslowski, P. Piskorz, G. Liu and D. Moncrieff, J. Phys. Chem., 1996, 100, 19333
29. (c) Y. Yamaguchi and T. Yamabe, Int. J. Quantum Chem., 1996, 57, 73.
30. A. A. El-Azhary and H. U. Suter, J. Phys. Chem., 1996, 100, 15056.
31. (a) G. Jung (Ed.) Combinatorial Peptide and Non-peptide Libraries, Wiley-VCH, Weinheim, 1996
32. (b) G. Jung (Ed.), Combinatorial Chemistry, Wiley-VCH, Weinheim, 1999.
33. G. Videnov, D. Kaiser, M. Brooks and G. Jung, Angew. Chem., 1996, 108, 1604
34. G. Videnov, D. Kaiser, M. Brooks and G. Jung, Angew. Chem., Int. Ed. Engl., 1996, 35, 1506.
35. G. M. Sheldrick, Acta Crystallogr., Sect. A, 1990, 46, 467.
36. G. M. Sheldrick, SHELXL-93, Program for Crystal Structure Refinement, University of Göttingen, 1993.
37. B. A. Frenz, Enraf-Nonius Structure Determination Package, SDP User's Guide, Enraf-Nonius, Delft, The Netherlands, 1983.
38. C. P. M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Peterson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortitz, J. B. Foresman, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez and J. A. Pople, GAUSSIAN 94; Revision B.3, Gaussian Inc., Pittsburgh, PA, 1995.
39. (a) P. C. Hariharan and J. A. Pople, Theor. Chim. Acta, 1973, 28, 213
40. (b) J. Hehre, R. D. Ditchfield and J. A. Pople, J. Chem. Phys., 1972, 56, 2257.
41. (a) A. D. Becke, J. Chem. Phys., 1993, 98, 1372
42. (b) A. D. Becke, J. Chem. Phys., 1993, 98, 5648.
43. C. Lee, W. Yang and R. G. Parr, Phys. Rev. B, 1988 37, 785.
44. W. J. Pietro, M. M. Francl, W. J. Hehre, D. J. Defrees, J. A. Pople and J. S. Binkley, J. Am. Chem. Soc., 1982, 104, 5039.
45. G. Schaftenaar, QCPE619 MOLDEN, A portable Electron Density Program, QCPE Bulletin, 1992, 12, 3.