Interactions of a β-dipeptide with monovalent metal cations: Crystal structures of (anthranoyl)anthranilic acid and its lithium, sodium and thallium salts

Journal of Inorganic Biochemistry

Volumn 98, Issue 3, 2004, Pages 473-484

  Wiesbrock, Frank ^a   Schmidbaur, Hubert ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

(Anthranoyl)anthranilic acid; Lithium; pKS value; Sodium and thallium complexes; X ray crystal structure analysis

Indexed keywords

(ANTHRANOYL)ANTHRANILIC ACID; ALKALI; ANTHRANILIC ACID DERIVATIVE; CARBONIC ACID; DIPEPTIDE DERIVATIVE; HYDROGEN; LIGAND; LITHIUM; METAL COMPLEX; MONOVALENT CATION; OXYGEN; SODIUM; THALLIUM; UNCLASSIFIED DRUG; WATER;

ARTICLE; COMPLEX FORMATION; CONFORMATION; CRYSTAL STRUCTURE; CRYSTALLIZATION; HYDROGEN BOND; MODEL; X RAY ANALYSIS;

ARENE;

EID: 1342286868     PISSN: 01620134     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jinorgbio.2003.12.017     Document Type: Article

References (53)

1. Dudev T., Lim C. Chem. Rev. 103:2003;773-787.
2. Hartwig A. Chem. Unserer Zeit. 34:2000;224-231.
3. Cowan J.A. Chem. Rev. 98:1998;1067-1087.
4. Frausto da Silva J.J.R., Williams R.J.P. The Biological Chemistry of the Elements. 1991;Clarendon Press, Oxford.
5. Sigel H. Metal Ions in Biological Systems. vol. 7:1976;Marcel Dekker, New York.
6. Williams R.J.P. Polyhedron. 6:1987;61-69.
7. Eichhorn G.L. Inorganic Biochemistry. vol. 1:1973;Elsevier, Amsterdam.
8. L.G. Sillén, A.E. Martell, Stability Constants of Metal Ion Complexes, The Chemical Society Special Publications, No. 17, London (1964)
9. Schmidbaur H., Classen H.G., Helbig J. Angew. Chem. Int. Ed. Engl. 29:1990;1090-1103. (review article).
10. Schmidbaur H., Bach I., Wilkinson D.L., Müller G. Chem. Ber. 122:1989;1427-1431.
11. Kashiwagi T., Sano C., Kawakita T., Nagashima N. Acta Cryst. 51C:1995;1053-1056.
12. Schmidbaur H., Mikulcik P., Müller G. Chem. Ber. 123:1990;1001-1004.
13. Schmidbaur H., Bach I., Wilkinson D.L., Müller G. Chem. Ber. 122:1989;1445-1447.
14. Schmidbaur H., Müller G., Riede J., Manniger G., Helbig J. Angew. Chem. Int. Ed. Engl. 25:1986;1013-1014.
15. Schmidbaur H., Wilkinson D.L., Schier A., Helbig J., Manninger G. New J. Chem. 18:1994;507-510.
16. Schmidbaur H., Bach I., Wilkinson D.L., Müller G. Chem. Ber. 122:1989;1433-1438.
17. Lu T., Li X., Mao Z., Qiu W., Ji L., Yu K. Polyhedron. 17:1997;75-79.
18. Schmidbaur H., Bach I., Wilkinson D.L., Müller G. Chem. Ber. 122:1989;1439-1444.
19. Einspahr H., Bugg C.E. Acta Cryst. 35B:1979;316-321.
20. Einspahr H., Bugg C.E. Acta Cryst. B. 30:1974;1037-1043.
21. Calvo R., Steren C.A., Piro O.E., Rojo T., Zuniga F.J., Castellano E.E. Inorg. Chem. 32:1993;6016-6022.
22. Gramaccioli C.M., Marsh R.E. Acta Cryst. 21:1966;594-600.
23. Antolini L., Menabue L., Pellacani G.C., Marcotrigiano G. J. Chem. Soc. Dalton Trans. 1982;2541-2543.
24. Schmidbaur H., Bach I., Riede J., Müller G., Helbig J., Hopf G. Chem. Ber. 120:1987;867-869.
25. Gramaccioli C.M. Acta Cryst. 21:1966;600-605.
26. Wiesbrock F., Schmidbaur H. Cryst. Eng. Commun. 5:2003;262-264
27. Abele S., Seebach D. Eur. J. Org. Chem. 2000;1-15.
28. Guichard G., Abele S., Seebach D. Helv. Chim. Acta. 81:1998;187-206.
29. Böhm A., Seebach D. Helv. Chim. Acta. 83:2000;3262-3278.
30. Wiesbrock F., Schmidbaur H. J. Chem. Soc. Dalton Trans. 2002;3201-3205.
31. Wiesbrock F., Nogai S., Schier A., Schmidbaur H. Helv. Chim. Acta. 85:2002;1151-1159.
32. Wiesbrock F., Schmidbaur H. Z. Naturforsch. 58B:2003;395-398.
33. Robertson D.E., Lesage S., Roberts M.F. Biochim. Biophys. Acta. 992:1989;320-326.
34. Eder J., Kutacek M. Biol. Plant. 14:1972;390-395.
35. Wiesbrock F., Schmidbaur H. J. Chem. Soc. Dalton Trans. 2002;4703-4708.
36. F. Wiesbrock, H. Schmidbaur, Inorg. Chem. 42 (2003) (accepted).
37. Wiesbrock F., Schier A., Schmidbaur H. Z. Naturforsch. 57B:2002;251-254.
38. Murugavel R., Karambelkar V.V., Anantharaman G., Walawalkar M.G. Inorg. Chem. 39:2000;1381-1390.
39. Lange B.A., Haendler H.M. J. Solid State Chem. 15:1975;325-332.
40. Boudreau S.M., Boudreau R.A., Haendler H.M. J. Solid State Chem. 49:1983;379-384.
41. Wiesbrock F., Schmidbaur H. J. Am. Chem. Soc. 125:2003;3622-3630.
42. Kristiansson O. Eur. J. Inorg. Chem. 2002;2355-2361.
43. Kaim W., Schwederski B. Bioanorganische Chemie. 1995;B.G. Teubner, Stuttgart.
44. Ravinder V., Venkatnarayana O., Mrudula Rao B.V., Swamy S.J., Lingaiah P. Ind. J. Chem. A. 23:1984;336-338.
45. Garg B.S., Kumar V., Reddy M.J. Trans. Met. Chem. 18:1993;364-368.
46. Ravindar V., Lingaiah P., Reddy K.V. Inorg. Chim. Acta. 87:1984;35-40.
47. Hoorfar A., Ollis W.D., Price J.A., Stephanatou J.S., Stoddart J.F. J. Chem. Soc. Perkin Trans. 1982;1649-1699.
48. Abdel-Monem Abdel-Hafez A. Bioorg. Med. Chem. 10:2002;2297-2302.
49. G.M. Sheldrick, SHELXS-97, Program for structure solution, University of Göttingen (1997)
50. G.M. Sheldrick, SHELXl-97, Program for crystal structure analysis, University of Göttingen (1997)
51. Galster H. pH-Messung: Grundlagen, Methoden, Anwendungen, Geräte. 1990;VCH, Weinheim.
52. Farmer M., Warth J. J. Chem. Soc. 85:1904;1726-1730.
53. C.K. Johnson, ORTEP, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, TN (1976)