Helically chiral ferrocene peptides containing 1′ -aminoferrocene-1-carboxylic acid subunits as turn inducers

Chemistry - A European Journal

Volumn 12, Issue 19, 2006, Pages 4965-4980

  Barišić, Lidija ^a   Čakić, Mojca ^a   Mahmoud, Khaled A ^b   Liu, You Nian ^b,e   Kraatz, Heinz Bernhard ^b   Pritzkow, Hans ^c   Kirin, Srećko I ^c   Metzler Nolte, Nils ^c,d   Rapić, Vladimir ^a  

^a UNIVERSITY OF ZAGREB   (Croatia)

^b UNIVERSITY OF SASKATCHEWAN   (Canada)

^c UNIVERSITY OF HEIDELBERG   (Germany)

^d RUHR UNIVERSITY BOCHUM   (Germany)

^e CENTRAL SOUTH UNIVERSITY   (China)

Author keywords

Amino acids; Bioorganometallic chemistry; Ferrocene; Hydrogen bonds; Peptides

Indexed keywords

BIOORGANOMETALLIC CHEMISTRY; CHIRAL FERROCENE PEPTIDES; HYDROGEN-BONDING PATTERNS; METALLOCENE; PEPTIDES;

AMINO ACIDS; CHEMICAL BONDS; INFRARED SPECTROGRAPHS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE; ORGANOMETALLICS; X RAY CRYSTALLOGRAPHY;

CARBOXYLIC ACIDS;

1' AMINOFERROCENE 1 CARBOXYLIC ACID; 1'-AMINOFERROCENE-1-CARBOXYLIC ACID; CARBOXYLIC ACID; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; FERROCENE; FERROUS ION; PEPTIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; CONFORMATION; INFRARED SPECTROPHOTOMETRY; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

CARBOXYLIC ACIDS; CIRCULAR DICHROISM; CRYSTALLOGRAPHY, X-RAY; FERROUS COMPOUNDS; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PEPTIDES; SPECTROPHOTOMETRY, INFRARED; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; STEREOISOMERISM;

EID: 33745700281     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200600156     Document Type: Article

References (51)

1. a) S. G. Zhang, Nat. Biotechnol. 2003, 21, 1171-1178;
2. b) V. Balzani, A. Credi, F. M. Raymo, J. F. Stoddart, Angew. Chem. 2000, 112, 3484-3530;
3. Angew. Chem. Int. Ed. 2000, 39, 3348-3391.
4. M. A. Shogren-Knaak, P. J. Alaimo, K. M. Shokat, Annu. Rev. Cell Dev. Biol. 2001, 17, 405-433.
5. T. Moriuchi, T. Hirao, Chem. Soc. Rev. 2004, 33, 294-301.
6. R. S. Herrick, R. M. Jarret, T. P. Curran, D. R. Dragoli, M. B. Flaherty, S. E. Lindyberg, R. A. Slate, L. C. Thornton, Tetrahedron Lett. 1996, 37, 5289-5292.
7. For recent reviews, see: a) D. R. van Staveren, N. Metzler-Nolte, Chem. Rev. 2004, 104, 5931-5985;
8. b) S. I. Kirin, H.-B. Kraatz, N. Metzler-Nolte, Chem. Soc. Rev. 2006, 35, 348-354.
9. a) M. J. Sheehy, J. F. Gallagher, M. Yamashita, Y. Ida, J. White-Colangelo, J. Johnson, R. Orlando, P. T. M. Kenny, J. Organomet. Chem. 2004, 689, 1511-1520;
10. b) D. Savage, G. Malone, J. F. Gallagher, Y. Ida, P. T. M. Kenny, J. Organomet. Chem. 2005, 690, 383-393.
11. a) A. Nomoto, T. Moriuchi, S. Yamazaki, A. Ogawa, T. Hirao, Chem. Commun. 1998, 1963-1964;
12. b) T. Moriuchi, A. Nomoto, K. Yoshida, A. Ogawa, T. Hirao, J. Am. Chem. Soc. 2001, 123, 68-75;
13. c) T. Moriuchi, A. Nomoto, K. Yoshida, T. Hirao, Organometallics 2001, 20, 1008-1013;
14. d) T. Moriuchi, K. Yoshida, T. Hirao, Org. Lett. 2003, 5, 4285-4288;
15. e) T. Moriuchi, K. Yoshida, T. Hirao, J. Organomet. Chem. 2003, 668, 31-34;
16. f) T. Moriuchi, T. Nagai, T. Hirao, Org. Lett. 2005, 7, 5265-5268;
17. g) T. Moriuchi, T. Nagai, T. Hirao, Org. Lett. 2006, 8, 31-34.
18. a) Y. Xu, P. Saweczko, H.-B. Kraatz, J. Organomet. Chem. 2001, 637-639, 335-342;
19. b) Y. Xu, H.-B. Kraatz, Tetrahedron Lett. 2001, 42, 2601-2603;
20. c) F. E. Appoh, T. C. Sutherland, H.-B. Kraatz, J. Organomet. Chem. 2004, 689, 4669-4677;
21. d) F. E. Appoh, T. C. Sutherland, H.-B. Kraatz, J. Organomet. Chem. 2005, 690, 1209-1217.
22. a) D. R. van Staveren, T. Weyhermüller, N. Metzler-Nolte, Dalton Trans. 2003, 210-220;
23. b) X. de Hatten, T. Weyhermüller, N. Metzler-Nolte, J. Organomet. Chem. 2004, 689, 4856-4867;
24. c) S. I. Kirin, D. Wissenbach, N. Metzler-Nolte, New J. Chem. 2005, 29, 1168-1173.
25. a) K. Heinze, M. Schlenker, Eur. J. Inorg. Chem. 2004, 2974-2988;
26. b) K. Heinze, M. Schlenker, Eur. J. Inorg. Chem. 2005, 66-71;
27. c) K. Heinze, M. Beckmann, Eur. J. Inorg. Chem. 2005, 3450-3457.
28. a) S. Chowdhury, G. Schatte, H.-B. Kraatź, Dalton Trans. 2004, 1726-1730;
29. b) S. Chowdhury, K. A. Mahmoud, G. Schatte, H.-B. Kraatz, Org. Biomol. Chem. 2005, 3, 3018-3023;
30. c) S. Chowdhury, D. A. R. Sanders, G. Schatte, H.-B. Kraatz, Angew. Chem. 2006, 118, 765-768;
31. Angew. Chem. Int. Ed. 2006, 45, 751-754;.
32. a) J. T. Yli-Kauhaluoma, J. A. Ashley, C.-H. Lo, L. Tucker, M. M. Wolfe, K. D. Janda, J. Am. Chem. Soc. 1995, 117, 7041-7047;
33. b) A. Heine, E. A. Stura, J. T. Yli-Kauhaluoma, C. Gao, Q. Deng, B. R. Beno, K. N. Houk, K. D. Janda, I. A. Wilson, Science 1998, 279, 1934-1940;
34. c) C. E. Cannizzaro, J. A. Ashley, K. D. Janda, K.N. Houk, J. Am. Chem. Soc. 2003, 125, 2489-2506.
35. Other synthetic pathways to Fca: a) I. R. Butler, S. C. Quayle, J. Organomet. Chem. 1998, 552, 63-68;
36. b) T. Okamura, K. Sakauye, N. Ueyama, A. Nakamura, Inorg. Chem. 1998, 37, 6731-6736; and references [10 a, 12 a, 14 a].
37. a) L. Barišić, V. Rapić, V. Kovač, Croat. Chem. Acta 2002, 75, 199-210;
38. b) G. Pavlović, L. Barisic, V. Rapic, I. Leban, Acta Crystallogr. Sect. E 2002, 58, m13-m15;
39. c) G. Pavlović, L. Barišić, V. Rapić, V. Kovač, Acta Cryst. Sect. C 2003, 59, m55-m57;
40. d) L. Barišić, V. Rapić, H. Pritzkow, G. Pavlović, I. Nemet, J. Organomet. Chem. 2003, 682, 131-142.
41. L. Barisic, M. Dropučič, V. Rapić, H. Pritzkow, S. I. Kirin, N. Metzler-Nolte, Chem. Commun. 2004, 2004-2005.
42. D. W. Hall, J. H. Richards, J. Org. Chem. 1963, 28, 1549-1554.
43. a) B. Ishimoto, K. Tonan, S. Ikawa, Spectrochim. Acta Part A 1999, 56, 201-209;
44. b) Y. Jin, K. Tonan, S. Ikawa, Spectrochim. Acta Part A 2002, 58, 2795-2802;
45. c) K. Tonan, S. Ikawa, Spectrochim. Acta Part A 2003, 59, 111-120.
46. N. Metzler-Nolte in Bioorganometallics (Ed.: G. Jaouen), Wiley-VCH, Weinheim, 2005, pp. 125-179.
47. a) A. Rodger, B. Norden, Circular Dichroism and Linear Dichroism, Oxford University Press, Oxford, UK, 1997;
48. b) S. M. Kelly, T. J. Jess, N. C. Price, Biochim. Biophys. Acta 2005, 7757, 119-139.
49. W. Bauer, K. Polborn, W. Beck, J. Organomet. Chem. 1999, 579, 269-279.
50. G. M. Sheldrick, SHELXTLV5.1, Bruker AXS, Madison, Wisconsin, 1998.
51. A. L. Spek, PLATON, Utrecht University, 1980-2005.