Synthesis and screening of libraries of synthetic tripodal receptor molecules with three different amino acid or peptide arms: Identification of iron binders

Journal of Combinatorial Chemistry

Volumn 4, Issue 4, 2002, Pages 275-284

  Opatz, Till ^a,b   Liskamp, Rob M J ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

^b JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; IRON; PEPTIDE;

ARTICLE; CHEMISTRY; COMBINATORIAL CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

AMINO ACIDS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COMBINATORIAL CHEMISTRY TECHNIQUES; IRON; MAGNETIC RESONANCE SPECTROSCOPY; PEPTIDES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 0036635727     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc020009s     Document Type: Article

References (47)

1. For examples, see the following, (a) Linton, B.; Hamilton, A. D. Curr. Opin. Chem. Biol. 1999, 3, 307.
2. (b) Goodman, M. S.; Jubian, V.; Linton, B.; Hamilton, A. D. J. Am. Chem. Soc. 1995, 117, 11610.
3. (c) Iorio, E. J.; Still, W. C. Bioorg. Med. Chem. Lett. 1999, 9, 2145.
4. (d) Iorio, E. J.; Shao, Y.; Chen, C.-T.; Wagner, H.; Still, W. C. Bioorg. Med. Chem. Lett. 2001, 11, 1635.
5. (e) Weingarten, M. D.; Sekanina, K.; Still, W. C. J. Am. Chem. Soc. 1998, 120, 9112.
6. (f) Shao, Y.; Still, W. C. J. Org. Chem. 1996, 61, 6086.
7. (g) Still, W. C. Acc. Chem. Res. 1996, 29, 155.
8. (h) Toneiro, M.; Still, W. C. Tetrahedron 1997, 56, 8739.
9. (a) Boyce, R.; Li, G.; Nestler, H. P.; Suenaga. T.; Still, W. C. J. Am. Chem. Soc. 1994, 116, 7955.
10. (b) Genari, C.; Nestler, H. P.; Salom, B.; Still, W. C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1765.
11. (c) Cheng, Y.; Suenaga, T.; Still, W. C. J. Am. Chem. Soc. 1996, 118, 1813.
12. (d) Löwik, D. W. P. M.; Mulders, S. J. E.; Cheng, Y.; Shao, Y.; Liskamp, R. M. J. Tetrahedron Lett. 1996, 37, 8252.
13. (e) Chen, C. W.; Whitlock, H. W., Jr. J. Am. Chem. Soc. 1978, 100, 4921.
14. (f) Fessmann, T.; Kilburn, J. D. Angew. Chem., Int. Ed. Engl. 1999, 38, 1993.
15. (g) Hioki, H.; Yamada, T.; Fujioka, C.; Kodama, M. Tetrahedron Lett. 1999, 40, 6821.
16. (h) Braxmeier, T.; Demarcus, M.; Fessmann, T.; McAteer, S.; Kilburn, J. D. Chem.-Eur. J. 2001, 7, 1889.
17. (i) Löwik, D. W. P. M.; Weingarten, M. D.; Broekema, M.; Brouwer, A. J.; Still, W. C.; Liskamp, R. M. J. Angew. Chem., Int. Ed. 1998, 37, 1846.
18. (j) Davies, M.; Bonnat, M.; Guillier, F.; Kilburn, J. D.; Bradley, M. J. Org. Chem. 1998, 63, 8696.
19. (k) Dong, D. L.; Ruiping, L.; Sherlock, R.; Wigler, M. H.; Nestler, H. P. Chem. Biol. 1999, 6, 133.
20. (l) Wennemers, H.; Conza, M.; Nold, M.; Krattiger, P. Chem. - Eur. J. 2001, 7, 3342.
21. (m) Schneider, S. E.; O'Neil, S. N.; Anslyn, E. V. J. Am. Chem. Soc. 2000, 122, 542.
22. (n) Botana, E.; Ongeri, S.; Arienzo, R.; Demarcus, M.; Frey, J. G.; Piarulli, U.; Potenza, D.; Gennari, C.; Killburn, J. D. Chem. Commun. 2001, 1358.
23. (o) Brouwer, A. J.; Van Der Linden, H. J.; Liskamp, R. M. J. J. Org. Chem. 2000, 65, 1750.
24. (p) De Muynck, H.; Madder, A.; Farcy, N.; De Clercq, P. J.; Pérez-Payán, N.; Öhberg, L. M.; Davis, A. P. Angew. Chem., Int. Ed. 2000, 39, 145.
25. Monnee, M. C. F.; Brouwer, A. J.; Verbeek, L. M.; van Wageningen, A. M. A.; Liskamp, R. M. J. Bioorg. Med. Chem. Lett. 2001, 11, 1521.
26. Opatz, T.; Liskamp, R. M. J. Org. Lett. 2001, 3, 3499.
27. (a) Floch, V.; Le Bolch, G.; Gable-Guillaume, C.; Le Bris, N.; Yaouanc, J.-J.: et al. Eur. J. Med. Chem. Chim. Ther. 1998, 33, 923.
28. (b) An. H.; Cummins, L. C.; Giffrey, R. H.; Bharadwaj, R.; Haly, B. D.; Fraser, A. S.; Wilson-Lingardo, L.; Rinsen, L. M.; Wyatt, J. R.; Cook, P. D. J. Am. Chem. Soc. 1997, 119, 3696.
29. Kurz, K.; Göbel, M. W. Helv. Chim. Acta 1996, 79, 1967.
30. For a similar alkylation see the following. Landini, D.; Penso, M. Synth. Commun. 1988, 18, 791.
31. (a) Edman, P. Acta Chem. Scand. 1950, 4, 283.
32. (b) Sequencing of peptoid peptidomimetics by Edman degradation: Boeijen, A.; Liskamp, R. M. J. Tetrahedron Lett. 1998, 39, 3589.
33. Furka, A.; Sebestyen. F.; Asgedom, M.; Dibo, G. Int. J. Pept. Protein Res. 1991, 37, 487 and references therein.
34. Vojkovsky, T. Pept. Res. 1995, 8, 236.
35. (a) Miller, J. C.; Scanlan, T. S. J. Am. Chem. Soc. 1997, 119, 2301.
36. (b) Reichwein, J. F.; Liskamp, R. M. J. Tetrahedron Lett. 1998, 39, 1243.
37. Honda, M.; Monta, H.; Nagakura, I. J. Org. Chem. 1997, 62, 8932.
38. (a) Francis, M. B.; Finney, N. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 8983.
39. (b) Burger, M. T.; Still, W. C. J. Org. Chem. 1995, 60, 7382.
40. 2+-binding by resin bound peptides in a partially combinatorial library: Shibata, N.; Baldwin, J. E.; Wood, M. E. Bioorg. Med. Chem. Lett. 1997, 7, 413.
41. 3+.
42. (a) Elango, N.; Radhakrishnan, R.; Froland, W. A.; Wallar, B. J.; Earhart, C. A.; Lipscomb, J. D.; Ohlendorf, D. H. Protein Sci. 1997, 6, 556. File 1mhy.pdb.
43. (b) Nordlund, P.; Eklund, H. Curr. Opin. Struct. Biol. 1995, 5, 758.
44. For databases on metalloproteins, see the following. (a) Degtyarenko, K. N.; North, A. C.; Findlay, J. B. Protein Eng. 1997, 10, 183 [http://bioinf.leeds.ac.uk/promise].
45. (b) Castagnetto, J. M.; Hennessy, S. W.; Roberts, V. A.; Getzoff, E. D.; Tainer, J. A.; Pique, M. E. Nucleic Acids Res. 2002, 30, 379 [http://metallo.scripps.edu].
46. -6 M still gave identifiable binders, indicating a high selectivity over a broad range of concentrations.
47. Stillman, T. J.; Hempstead, P. D.; Hudson, A. J.; Artymiuk, P. J.; Andrews, S. C.; Hudson, A. J.; Treffey, A.; Guest, J. R.; Harrison, P. M. J. Mol. Biol. 2001, 307, 587. File leum.pdb.