Copper(II) complexes of the tetraazamacrocyclic tertiary amide ligand alanyl-cyclam

European Journal of Inorganic Chemistry

Volumn , Issue 12, 2006, Pages 2357-2363

  Schickaneder, Christian ^a   Heinemann, Frank W ^a   Alsfasser, Ralf ^b  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

^b UNIVERSITY OF FREIBURG   (Germany)

Author keywords

Bioinorganic chemistry; Copper; Cyclam; Electrophilic activation; Winkler Dunitz parameters

Indexed keywords

AMIDES; AMINO ACIDS; BIOCHEMISTRY; CHEMICAL ACTIVATION; COPPER COMPOUNDS; HYDROGEN BONDS; LIGANDS;

AMIDE LIGANDS; BIOINORGANIC CHEMISTRY; BOND ROTATIONS; CARBOXAMIDES; CYCLAM; ELECTROPHILIC ACTIVATION; NITROGEN ATOM; TERTIARY AMIDES; WINKL-DUNITZ PARAMETER; WINKLER;

METAL COMPLEXES;

EID: 33745647322     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.200600055     Document Type: Article

References (49)

1. a) Z. Wang, W. Fast, A. M. Valentine, S. J. Benkovic, Curr. Opin. Chem. Biol. 1999, 3, 614;
2. b) J. D. Garrity, B. Bennett, M. W. Crowder, Biochemistry 2005, 44, 1078.
3. G. Fischer, T. Aumüller, Rev. Physiol. Biochem. Pharmacol. 2003, 148, 105.
4. a) A. H. Andreotti, Biochemistry 2003, 42, 9515;
5. b) K. K.-S. Ng, W. I. Weis, Biochem. 1998, 37, 17977.
6. E. Cohen, A. Taraboulos, EMBO J. 2003, 22, 404.
7. a) C. Dugave, L. Demange, Chem. Rev. 2003, 103, 2475;
8. b) G. Fischer, Chem. Soc. Rev. 2000, 29, 119.
9. a) S. Hur, T. C. Bruice, J. Am. Chem. Soc. 2002, 124, 7303;
10. b) G. Li, Q. Cui, J. Am. Chem. Soc. 2003, 125, 15028.
11. U. Reimer, N. E. Mokdad, M. Schutkowski, G. Fischer, Biochemistry 1997, 36, 13802.
12. a) P. A. Temussi, F. Quadrifoglio, J. Chem. Soc., Chem. Commun. 1968, 844;
13. b) W. E. Waghorn, A. J. I. Ward, T. G. Clune, B. G. Cox, J. Chem. Soc., Faraday Trans. 1 1980, 76, 1131.
14. a) C. Cox, T. Lectka, Acc. Chem. Res. 2000, 33, 849;
15. b) C. Cox, D. Feraris, N. N. Murthy, T. Lectka, J. Am. Chem. Soc. 1996, 118, 5332.
16. a) N. Niklas, F. Hampel, G. Liehr, A. Zahl, R. Alsfasser, Chem. Eur. J. 2001, 7, 5135;
17. b) N. Niklas, F. W. Heinemann, F. Hampel, R. Alsfasser, Angew. Chem. 2002, 114, 3535;
18. Angew. Chem. Int. Ed. 2002, 41, 3386;
19. c) N. Niklas, F. W. Heinemann, F. Hampel, T. Clark, R. Alsfasser, Inorg. Chem. 2004, 43, 4663.
20. S. Brandès, C. Gros, F. Denat, P. Pullumbi, R. Guilard, Bull. Soc. Chim. Fr. 1996, 133, 65.
21. W. König, R. Geiger, Chem. Ber. 1970, 103, 788.
22. B. Geißer, B. König, R. Alsfasser, Eur. J. Inorg. Chem. 2001, 1543.
23. a) R. B. Penland, S. Mizushima, C. Curran, J. V. Quagliano, J. Am. Chem. Soc. 1957, 79, 1575;
24. b) P. Maslak, J. J. Sczepanski, M. Parvez, J. Am. Chem. Soc. 1991, 113, 1991;
25. c) D. P. Failie, T. C. Woon, W. A. Wickramasinghe, A. C. Willis, Inorg. Chem. 1994, 33, 6425.
26. A. Mondal, E. L. Klein, M. A. Khan, R. P. Houser, Inorg. Chem. 2003, 42, 5462.
27. a) H. C. Freeman, Inorg. Biochem. 1973, 1, 121;
28. b) H. Sigel, R. B. Martin, Chem. Rev. 1982, 82, 385.
29. For other applications of Cbz-protected macrocyclic ligands see, for example; R. Reichenbach-Klinke, M. Zabel, B. König, Dalton Trans. 2003, 141.
30. F. K. Winkler, J. D. Dunitz, J. Mol. Biol. 1971, 59, 169.
31. K. B. Wiberg in: The Amide Linkage: Structural Aspects in Chemistry, Biochemistry and Material Science (Eds.: A. Greenberg, C. M. Breneman, J. F. Liebman), John Wiley & Sons, Hoboken, 2003, p. 33.
32. G. Gilli, V. Bertolasi, F. Bellucci, V. Ferretti, J. Am. Chem. Soc. 1986, 108, 2420.
33. a) A. Greenberg, C. A. Venanzi, J. Am. Chem. Soc. 1993, 115, 6951;
34. b) Y. Otani, O. Nagae, Y. Naruse, S. Inagaki, M. Ohno, K. Yamaguchi, G. Yamamoto, M. Uchiyama, T. Ohwada, J. Am. Chem. Soc. 2003, 125, 15191;
35. c) T. Ohwada, T. Achiwa, I. Okamoto, K. Shudo, Tetrahedron Lett. 1998, 39, 865;
36. d) G. Yamamoto, N. Tsubai, H. Murakami, Y. Mazaki, Chem. Lett. 1997, 1295;
37. e) A. J. Kirby, I. V. Komarov, N. Feeder, J. Chem. Soc., Perkin Trans. 2 2001, 522.
38. a) B. Bosnich, C. K. Poon, M. L. Tobe, Inorg. Chem. 1965, 4, 1102;
39. b) X. Liang, P. J. Sadler, Chem. Soc. Rev. 2004, 33, 246.
40. M. A. Donnelly, M. Zimmer, Inorg. Chem. 1999, 38, 1650.
41. K. F. Sibbons, M. Al-Hashimi, M. Motevalli, J. Wolowska, M. Watkinson, Dalton Trans. 2004, 3163.
42. A. J. Blake, I. A. Fallis, R. O. Gould, S. Parsons, S. A. Ross, M. Schröder, J. Chem. Soc., Chem. Commun. 1994, 2467.
43. N. Wiberg, Hollemann/Wiberg: Lehrbuch der Anorganischen Chemie, W. de Gruyter, Berlin, 1995.
44. L. Pauling, The Nature of the Chemical Bond, Cornell University Press, Cornell, 1948.
45. M. Schatz, M. Leibold, S. P. Foxon, M. Weitzer, F. W. Heinemann, F. Hampel, O. Walter, S. Schindler, Dalton Trans. 2003, 1480.
46. A. J. Kirby, I. V. Komarov, P. D. Wothers, N. Feeder, Angew. Chem. Int. Ed. Engl. 1998, 37, 785.
47. Bruker-AXS, Inc., SADABS, Madison, WI, USA, 2002.
48. a) Bruker-AXS, Inc., SHELXTL NT 6.12, Madison, WI, USA, 2002;
49. b) H. D. Flack, Acta Crystallogr., Sect. A 1983, 39, 876.