TACN-amino acid conjugates and their copper(II) complexes

Inorganic Chemistry

Volumn 42, Issue 18, 2003, Pages 5462-5464

  Mondal, Arunendu ^a   Klein, Eric L ^a   Khan, Masood A ^a   Houser, Robert P ^a  

^a UNIVERSITY OF OKLAHOMA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALANINE; AMINO ACID; CARBONYL DERIVATIVE; COPPER COMPLEX; GLYCINE; LIGAND; NITROGEN; PHENYLALANINE; TRIAZACYCLONONANE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BINDING; COMPLEX FORMATION; CRYSTAL STRUCTURE; PHASE TRANSITION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

AMINO ACIDS; AZA COMPOUNDS; COPPER; CRYSTALLOGRAPHY, X-RAY; ELECTRON SPIN RESONANCE SPECTROSCOPY; LIGANDS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PIPERIDINES;

EID: 0041374243     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic034598y     Document Type: Article

References (24)

1. Roat-Malone, R. M. Bioinorganic Chemistry: A Short Course; John Wiley & Sons: Hoboken, NJ, 2002.
2. Karlin, K. D. Science 1993, 261, 701-708.
3. Recent examples of ligand-amino acid conjugates: (a) Cox, C.; Ferraris, D.; Murthy, N. N.; Lectka, T. J. Am. Chem. Soc. 1996, 118, 5332-5333. (b) Niklas, N,; Heinemann, F. W.; Hampel, F.; Alsfasser, R. Angew. Chem. 2002, 41, 3386-3388. (c) Niklas, N.; Hampel, F.; Liehr, G.; Zahl, A.; Alsfasser, R. Chem. Eur. J. 2001, 7, 5135-5142. (d) Niklas, N.; Walter, O.; Alsfasser, R. Eur. J. Inorg. Chem. 2000, 1723-1731. (e) Ósz, K.; Várnagy, K.; Sóvágó, I.; Lennert, L.; Süli-Vargha, H.; Danna, D.; Micera, G. New J. Chem. 2001, 25, 700-706. (f) Ósz, K.; Várnagy, K.; Süli-Vargha, H.; Sanna, D.; Micera, G.; Sóvágó, I. Inorg. Chim. Acta 2002, 339, 373-382.
4. Recent examples of ligand-amino acid conjugates: (a) Cox, C.; Ferraris, D.; Murthy, N. N.; Lectka, T. J. Am. Chem. Soc. 1996, 118, 5332-5333. (b) Niklas, N,; Heinemann, F. W.; Hampel, F.; Alsfasser, R. Angew. Chem. 2002, 41, 3386-3388. (c) Niklas, N.; Hampel, F.; Liehr, G.; Zahl, A.; Alsfasser, R. Chem. Eur. J. 2001, 7, 5135-5142. (d) Niklas, N.; Walter, O.; Alsfasser, R. Eur. J. Inorg. Chem. 2000, 1723-1731. (e) Ósz, K.; Várnagy, K.; Sóvágó, I.; Lennert, L.; Süli-Vargha, H.; Danna, D.; Micera, G. New J. Chem. 2001, 25, 700-706. (f) Ósz, K.; Várnagy, K.; Süli-Vargha, H.; Sanna, D.; Micera, G.; Sóvágó, I. Inorg. Chim. Acta 2002, 339, 373-382.
5. Recent examples of ligand-amino acid conjugates: (a) Cox, C.; Ferraris, D.; Murthy, N. N.; Lectka, T. J. Am. Chem. Soc. 1996, 118, 5332-5333. (b) Niklas, N,; Heinemann, F. W.; Hampel, F.; Alsfasser, R. Angew. Chem. 2002, 41, 3386-3388. (c) Niklas, N.; Hampel, F.; Liehr, G.; Zahl, A.; Alsfasser, R. Chem. Eur. J. 2001, 7, 5135-5142. (d) Niklas, N.; Walter, O.; Alsfasser, R. Eur. J. Inorg. Chem. 2000, 1723-1731. (e) Ósz, K.; Várnagy, K.; Sóvágó, I.; Lennert, L.; Süli-Vargha, H.; Danna, D.; Micera, G. New J. Chem. 2001, 25, 700-706. (f) Ósz, K.; Várnagy, K.; Süli-Vargha, H.; Sanna, D.; Micera, G.; Sóvágó, I. Inorg. Chim. Acta 2002, 339, 373-382.
6. Recent examples of ligand-amino acid conjugates: (a) Cox, C.; Ferraris, D.; Murthy, N. N.; Lectka, T. J. Am. Chem. Soc. 1996, 118, 5332-5333. (b) Niklas, N,; Heinemann, F. W.; Hampel, F.; Alsfasser, R. Angew. Chem. 2002, 41, 3386-3388. (c) Niklas, N.; Hampel, F.; Liehr, G.; Zahl, A.; Alsfasser, R. Chem. Eur. J. 2001, 7, 5135-5142. (d) Niklas, N.; Walter, O.; Alsfasser, R. Eur. J. Inorg. Chem. 2000, 1723-1731. (e) Ósz, K.; Várnagy, K.; Sóvágó, I.; Lennert, L.; Süli-Vargha, H.; Danna, D.; Micera, G. New J. Chem. 2001, 25, 700-706. (f) Ósz, K.; Várnagy, K.; Süli-Vargha, H.; Sanna, D.; Micera, G.; Sóvágó, I. Inorg. Chim. Acta 2002, 339, 373-382.
7. Recent examples of ligand-amino acid conjugates: (a) Cox, C.; Ferraris, D.; Murthy, N. N.; Lectka, T. J. Am. Chem. Soc. 1996, 118, 5332-5333. (b) Niklas, N,; Heinemann, F. W.; Hampel, F.; Alsfasser, R. Angew. Chem. 2002, 41, 3386-3388. (c) Niklas, N.; Hampel, F.; Liehr, G.; Zahl, A.; Alsfasser, R. Chem. Eur. J. 2001, 7, 5135-5142. (d) Niklas, N.; Walter, O.; Alsfasser, R. Eur. J. Inorg. Chem. 2000, 1723-1731. (e) Ósz, K.; Várnagy, K.; Sóvágó, I.; Lennert, L.; Süli-Vargha, H.; Danna, D.; Micera, G. New J. Chem. 2001, 25, 700-706. (f) Ósz, K.; Várnagy, K.; Süli-Vargha, H.; Sanna, D.; Micera, G.; Sóvágó, I. Inorg. Chim. Acta 2002, 339, 373-382.
8. Recent examples of ligand-amino acid conjugates: (a) Cox, C.; Ferraris, D.; Murthy, N. N.; Lectka, T. J. Am. Chem. Soc. 1996, 118, 5332-5333. (b) Niklas, N,; Heinemann, F. W.; Hampel, F.; Alsfasser, R. Angew. Chem. 2002, 41, 3386-3388. (c) Niklas, N.; Hampel, F.; Liehr, G.; Zahl, A.; Alsfasser, R. Chem. Eur. J. 2001, 7, 5135-5142. (d) Niklas, N.; Walter, O.; Alsfasser, R. Eur. J. Inorg. Chem. 2000, 1723-1731. (e) Ósz, K.; Várnagy, K.; Sóvágó, I.; Lennert, L.; Süli-Vargha, H.; Danna, D.; Micera, G. New J. Chem. 2001, 25, 700-706. (f) Ósz, K.; Várnagy, K.; Süli-Vargha, H.; Sanna, D.; Micera, G.; Sóvágó, I. Inorg. Chim. Acta 2002, 339, 373-382.
9. Copper complexes with simple amino acids and oligopeptides are well-known. See for example: Harford, C.; Sarkar, B. Acc. Chem. Res. 1997, 30, 123-130.
10. Schmidt, B.; Ehlert, D. K. Tetrahedron Lett. 1998, 39, 3999-4002.
11. A similar synthetic approach was used to functionalize cyclen with amino acids: Geisser, B.; König, B.; Alsfasser, R. Eur. J. Inorg. Chem. 2001, 1543-1549.
12. Kimura, S.; Bill, E.; Bothe, E.; Weyhermüller, T.; Wieghardt, K. J. Am. Chem. Soc. 2001, 123, 6025-6039.
13. See Supporting Information.
14. Stephens, J. C.; Khan, M. A.; Houser, R. P. Inorg. Chem. 2001, 40, 5064-5065.
15. 4O: C, 33.04; H, 4.44; N, 10.27. Found: C, 32.78; H, 4.91; N, 10.21.
16. Data collection was performed on a Bruker Apex CCD diffractometer with Mo Kα radiation (0.71073 Å) at 143 K for 2 and 120 K for 3. See Supporting Information for full details.
17. 2 converged with R1 = 0.0505, wR2 = 0.1334, GOF = 1.051 for 6919 independent reflections with I > 2σ(I) and 492 parameters.
18. The most likely origin of the chloride is either contamination in the ligand or in the cupric perchlorate.
19. This is not surprising in light of the poor coordinating ability of tertiary amides. See Greenberg, A. In The Amide Linkage; Greenberg, A., Breneman, C. M., Liebman, J. F., Eds.; Wiley-Interscience: New York, 2000, pp 47-84.
20. This type of chelating binding mode for amino acids is relatively common and, in particular, has been reported for copper(II) amino acid species. (a) Tan, X. S.; Fujii, Y.; Sato, T.; Nakano, Y.; Yashiro, M. Chem. Commun. 1999, 881-882. (b) Castellano, E. E.; Piro, O. E.; Casado, N. M. C.; Brondino, C. D.; Calvo, R. J. Chem. Crystallogr. 1998, 28, 61-68.
21. This type of chelating binding mode for amino acids is relatively common and, in particular, has been reported for copper(II) amino acid species. (a) Tan, X. S.; Fujii, Y.; Sato, T.; Nakano, Y.; Yashiro, M. Chem. Commun. 1999, 881-882. (b) Castellano, E. E.; Piro, O. E.; Casado, N. M. C.; Brondino, C. D.; Calvo, R. J. Chem. Crystallogr. 1998, 28, 61-68.
22. Addison, A. W.; Rao, T. N.; Reedijk, J.; van Rijn, J.; Verschoor, G. C. J. Chem. Soc., Dalton Trans. 1984, 1349-1356.
23. 2 converged with R1 = 0.0221, wR2 = 0.0492, GOF = 1.005 for 3795 independent reflections with I > 2σ(I) and 235 parameters.
24. The dihedral angle between the Cl1-Cu1-Cl2 plane and the N1-Cu1-N2 plane is 14°. The dihedral angle between the Cl3-Cu2-Cl4 plane and the O1-Cu2-N4 plane is 6°.