Organometallic β-turn mimetics. A structural and spectroscopic study of inter-strand hydrogen bonding in ferrocene and cobaltocenium conjugates of amino acids and dipeptides

Dalton Transactions

Volumn , Issue 2, 2003, Pages 210-220

  Van Staveren, Dave R ^a,b   Weyhermüller, Thomas ^a   Metzler Nolte, Nils ^b  

^a MAX PLANCK INSTITUTE FOR CHEMICAL ENERGY CONVERSION   (Germany)

^b UNIVERSITY OF HEIDELBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CARBOXYLIC ACIDS; ELECTROCHEMISTRY; HYDROGEN BONDS; INFRARED RADIATION; MASS SPECTROMETRY; NITROGEN COMPOUNDS; NUCLEAR MAGNETIC RESONANCE; SINGLE CRYSTALS; SPECTROSCOPIC ANALYSIS; X RAY DIFFRACTION;

MIMETICS; PEPTIDES; SINGLE CRYSTAL X-RAY DIFFRACTION; SOLID STATE STRUCTURES;

ORGANOMETALLICS;

EID: 24644451215     PISSN: 14779226     EISSN: None     Source Type: Journal    
DOI: 10.1039/b208363a     Document Type: Article

References (45)

1. L. Stryer, Biochemistry, W. H. Freeman and Company, San Francisco, 1994.
2. D. P. Fairlie, M. L. West and A. K. Wong, Curr. Med. Chem., 1998, 5, 29-62.
3. D. Obrecht, M. Altorfer and J. A. Robinson, Adv. Med. Chem., 1999, 4, 1-68.
4. G. Hölzemann, Kontakte (Darmstadt), 1991, 1, 3-13;
5. G. Hölzemann, Kontakte (Darmstadt), 1991, 2, 55-64.
6. R. S. Herrick, R. M. Jarret, T. P. Curran, D. R. Dragoli, M. B. Flaherty, S. E. Lindyberg, R. A. Slate and L. C. Thornton, Tetrahedron Lett., 1996, 37, 5289-5292.
7. A. Nomoto, T. Moriuchi, S. Yamazaki, A. Ogawa and T. Hirao, Chem. Commun., 1998, 1963-1964.
8. T. Moriuchi, A. Nomoto, K. Yoshida and T. Hirao, J. Organomet. Chem., 1999, 589, 50-58.
9. T. Moriuchi, A. Nomoto, K. Yoshida, A. Ogawa and T. Hirao, J. Am. Chem. Soc., 2000, 123, 68-75.
10. T. Moriuchi, A. Nomoto, K. Yoshida and T. Hirao, Organometallics, 2001, 20, 1008-1013.
11. A. Togni and T. Hayashi, Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Material Science, VCH, Weinheim, 1995.
12. N. J. Long, Metallocenes, Blackwell Science, Oxford, 1998.
13. J. Meienhofer, The Mixed Carbonic Anhydride Method of Peptide Synthesis, Academic Press, London, 1979.
14. J. E. Sheats and M. D. Rausch, J. Org. Chem., 1970, 35, 3245-3249.
15. G. M. Sheldrick, SADABS, University of Göttingen, 1994.
16. A. L. Spek, L. J. Farrugia, in PLATON99, Utrecht, 1999.
17. G. M. Sheldrick, ShelXTL, University of Göttingen, 1994.
18. W. Bauer, K. Polborn and W. Beck, J. Organomet. Chem., 1999, 579, 269-279.
19. D. R. van Staveren, T. Weyhermüller and N. Metzler-Nolte, Organometallics, 2000, 19, 3730-3735.
20. M. Oberhoff, L. Duda, J. Karl, R. Mohr, G. Erker, R. Fröhlich and M. Grehl, Organometallics, 1996, 15, 4005-4011.
21. A. S. Georgopoulou, D. M. P. Mingos, A. J. P. White, D. J. Williams, B. R. Horrocks and A. Houlton, J. Chem. Soc., Dalton Trans., 2000, 2969-2974.
22. H. B. Kraatz, D. M. Leek, A. Houmam, G. D. Enright, J. Lusztyk and D. D. M. Wayner, J. Organomet. Chem., 1999, 589, 38-49.
23. O. Brosch, T. Weyhermüller and N. Metzler-Nolte, Eur. J. Inorg. Chem., 2000, 323-330.
24. M. C. Grossel, M. R. Goldspink, J. A. Hriljac and S. C. Weston, Organometallics, 1991, 10, 851-860.
25. L. Lin, A. Berces and H.-B. Kraatz, J. Organomet. Chem., 1998, 556, 11-20.
26. T. Moriuchi, I. Ikeda and T. Hirao, Organometallics, 1995, 14, 3578-3580.
27. T. A. Albright, J. K. Burdett and M.-H. Whangbo, Orbital Interactions in Chemistry, John Wiley & Sons, New York, 1985.
28. C. D. Hall, I. P. Danks, S. C. Nyburg, A. W. Parkins and N. W. Sharpe, Organometallics, 1990, 9, 1602-1607.
29. G.-B. Liang, G. P. Dado and S. H. Gellman, J. Am. Chem. Soc., 1991, 113, 3994-3995.
30. S. H. Gellman, G. P. Dado, G.-B. Liang and B. R. Adams, J. Am. Chem. Soc., 1991, 113, 1164-1173.
31. C. N. Kirsten and T. H. Schrader, J. Am. Chem. Soc., 1997, 119, 12061-12068.
32. Although every effort was made to work under stringent conditions, this result should be taken with appropriate care. Compound 7b is very hygroscopic and the presence even of trace amounts of water would already influence the measurements significantly.
33. G. C. K. Roberts, in NMR of Macromolecules - A Practical Approach, ed. D. Rickwood, B. D. Hames, Oxford University Press, Oxford, 1993.
34. H. Günther, NMR Spectroscopy, John Wiley & Sons, New York, 1980.
35. NH stretch vibration in the infrared spectrum and the chemical shift of the amide NH hydrogen atoms.
36. M. V. Baker, H.-B. Kraatz and J. W. Quail, New J. Chem., 2001, 25, 427-433.
37. H.-B. Kraatz, J. Lusztyk and G. D. Enright, Inorg. Chem., 1997, 36, 2400-2405.
38. A. Haaland, Acc. Chem. Res., 1979, 12, 415-422.
39. N. N. Greenwood and T. C. Gibb, Mössbauer Spectroscopy, Chapman and Hall, London, 1971.
40. R. M. G. Roberts and J. Silver, J. Organomet. Chem., 1984, 263, 235-241.
41. C. M. Venkatachalam, Biopolym., 1968, 6, 1425-1434.
42. E. G. Hutchinson and J. M. Thornton, Protein Sci., 1994, 3, 2207-2216.
43. C. M. Wilmot and J. M. Thornton, J. Mol. Biol., 1988, 203, 221-232.
44. M. Feigel, J. Am. Chem. Soc., 1986, 108, 181-182.
45. M.-H. Koepp, H. Wendt and H. Strehlow, Z. Elektrochem., Ber. Bunsenges. Phys. Chem., 1960, 64, 483.