A methylenic group binds guanidinoacetic acid to glycine and serine in two novel copper(II) complexes: Synthesis, X-ray structure and spectroscopic characterization

Polyhedron

Volumn 26, Issue 15, 2007, Pages 4363-4372

  Versiane, O ^a   Rodrigues, B L ^b   de Miranda, J L ^c   Ramos, Joanna Maria ^a   Téllez S, Claudio A ^d   Felcman, J ^a  

^a PONTIFICAL CATHOLIC UNIVERSITY OF RIO DE JANEIRO   (Brazil)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

^c FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

^d FLUMINENSE FEDERAL UNIVERSITY   (Brazil)

Author keywords

Copper(II); Glycine; Guanidinoacetic acid; Methylation; Serine

Indexed keywords

ACETIC ACID; ALKYLATION; CARBON; CARBOXYLATION; COPPER COMPOUNDS; DENSITY FUNCTIONAL THEORY; INDIUM COMPOUNDS; INFRARED SPECTROSCOPY; METHYLATION; PH; REACTION INTERMEDIATES; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

AMINO-ACIDS; COMPLEX 1; COPPER(II); GUANIDINOACETIC ACIDS; METHYLENIC GROUP; SERINE; SPECTROSCOPIC CHARACTERIZATION; STRUCTURE CHARACTERIZATION; SYNTHESISED; X-RAY STRUCTURE;

AMINO ACIDS;

EID: 34548242246     PISSN: 02775387     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.poly.2007.05.029     Document Type: Article

References (58)

1. Takeda M., Nakayama S., Tomino Y., Jung Y., Endou H., and Koide H. In: P Deyn P., Marescau B., Stalon V., and Qureshi I.A. (Eds). Guanidino Compounds in Biology and Medicine (1992), John Libbey & Company Ltd. 153-157
2. Stöckler S., Holzbach U., Hanefeld F., Marquardt I., Helms G., Requart M., Hanicke W., and Frahm J. Pediatr. Res. 36 (1994) 409
3. Neu A., Neuhoff H., Trube G., Fehr S., Ulrich K., Roeper J., and Isbrandt D. Neurobiol. Dis. 11 (2002) 298
4. Zugno A.I., Stefanello F.M., Streck E.L., Calcagnotto T., Wannmacher C.M.D., Wajner M., and Wyse A.T.S. Int. J. Develop. Neurosci. 21 (2003) 183
5. Alessandri M.G., Celati L., Battini R., Baldinotti F., Item C., Leuzzi V., and Cioni G. Anal. Biochem. 331 (2004) 189
6. Shulze A., Ebinger F., Rating D., and Mayaetepek E. Mol. Genet. Metab. 74 (2001) 413
7. Leuzzi V., Bianchi M.C., Tosetti M., Carducci C., Cerquiglini C.A., Cioni G., and Antonozzi I. Neurology 55 (2000) 1407
8. Schulze A., Hess T., Wevers R., Mayatepek E., Bachert P., Marescau B., Knopp M.V., Deyn P.P., Bremer H.J., and Rating D. J. Pediatr. 131 (1997) 626
9. Stöckler S., Holzbach U., Hanefeld F., Marquardt I., Helms G., Requart M., et al. Pediatr. Res. 36 3 (1994) 409
10. Stöckler S., Marescau B., De Deyn P.P., Trijbels J., and Hanefeld F. Metabolism 46 10 (1997) 1189
11. Shulze A. Mol. Cell Biochem. 244 1-2 (2003) 143
12. Ishizaki M., Kitamura H., Taguma Y., Aoyagi K., and Narita M. In: Deyn P., Marescau B., Stalon V., and Qureshi I.A. (Eds). Guanidino Compounds in Biology and Medicine (1992), John Libbey & Company Ltd. 275-280
13. Cohen B.D., and Patel H. In: Deyn P.P., Marescau B., Stalon V., and Qureshi I.A. (Eds). Guanidino Compounds in Biology and Medicine (1992), John Libbey & Company Ltd. 255-260
14. Levillain O., Marescau B., and Deyn P.P. In: Deyn P.P., Marescau B., Qureshi I.A., and Mori A. (Eds). Guanidino Compounds in Biology and Medicine vol. 2 (1997), John Libbey & Company Ltd. 289-297
15. Neu A., Neuhoff H., Trube G., Ulrich K., Roeper J., and Isbrandt D. Neurobiol. Dis. 11 2 (2002) 298
16. Zugno A.I., Stefanello F.M., Streck E.L., Calcagnotto T., Wannmacher C.M.D., Wajner M., and Wyse A.T.S. Int. J. Develop. Neurosci. 21 (2003) 183
17. Sugyiama K., Ohishi A., Syiu H., and Takeuchi H. J. Nutr. Sci. Vitaminol. 35 (1989) 613
18. Verhelst J., Berwaerts J., Marescau B., Abs R., Neels H., and Mahler C. Metab. Clin. Exp. 46 (1997) 1063
19. Mori A., Kohno M., Masumizu T., Noda Y., and Packer L. Biochem. Mol. Biol. Int. 40 (1996) 135
20. Deyn P.P., Marescau B., D'Hooge R., Possemiers I., Nagler J., and Mahler C.H. Neurochem. Int. 27 (1995) 227
21. Kuroda M. Nephron 65 (1993) 605
22. Yasuda M., Sugahara K., Zhang J., Shuin T., and Kodama H. Physiol. Chem. Phys. Med NMR 32 (2000) 119
23. Felcman J., and Miranda J.L. J. Braz. Chem. Soc. 8 6 (1997) 575
24. Miranda J.L., and Felcman J. Synth. React. Inorg. Met-Org Chem. 31 5 (2001) 873
25. Miranda J.L., and Felcman J. Polyhedron 22 (2003) 225
26. Tainer J.A., Getzoff E.D., Richard J.S., and Richardson D.C. Nature 306 (1983) 284
27. Wyatt R., and Sodoroski J. Science 280 (1998) 284
28. Miranda J.L., Felcman J., Wardell J.L., and Skakle J.S. Acta Crystallogr., Sect. C 58 (2002) m471
29. Felcman J., Alan Howie R., Miranda J.L., Skakle J.M.S., and Wardell J.L. Acta Crystallogr., Sect. C 59 (2003) m103
30. Miranda J.L., Felcman J., Versiane O., and Herbst M.H. Inorg. Chem. Commun. 7 (2004) 1198
31. Yamauchi Y., Sugimoto T., Sueyoshi K., Oji Y., and Tanaka K. Phytochemistry 58 5 (2001) 677
32. Zhao C.R., Shang L., Wang W., and Jacobs D.O. J. Surg. Res. 105 1 (2002) 10
33. Hannon C.L., and Auslyn E.V. In: Dugas H., and Schmidtchen F.P. (Eds). Bioorganic Chemistry Frontiers vol. 3 (1993), Springer, Berlin 192
34. Grenhil J.L., and Lue P. In: Ellis G.P., and Luscombe D.K. (Eds). Progress in Medicinal Chemistry vol. 30 (1993), Elsevier Science, New York (Chapter 5)
35. Enraf-Nonius collect. Nonius BV, Delft, The Netherlands (1997-2000).
36. Parr R.G., and Yang W. Density-Functional Theory of Atoms and Molecules (1989), Oxford University Press, Oxford
37. Becke A.D. J. Chem. Phys. 98 (1993) 1372
38. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Zakrzewski Jr. V.G., Montgomery J.A., Stratmann R.E., Burant J.C., Dapprich S., Millam J.M., Daniels A.D., Kudin K.N., Strain M.C., Farkas O., Tomasi J., Barone V., Cossi NM., Cammi R., Mennucci B., ÇPomelli C., Adamo C., Clifford S., Ochterski J., Peterson G.A., Ayala P.Y., Cui Q., Morokuma K., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Cioslowski J., Ortiz J.V., Baboul A.G., Stepanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Gomperts R., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., González C., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Andresw J.L., González C., Head-Gordon M., Repogle E.S., and Pople J.A. gaussian 98, Revision A.7 (1998), Gaussian Inc., Pittsburgh, PA
39. Masuda H., Odani A., Yamazaki T., Yajima T., and Yamauchi O. Inorg. Chem. 32 (1993) 1111
40. Weeks C.M., Cooper A., and Norton D.A. Acta Crystallogr., Sect. B 25 (1969) 443
41. Freeman H.C., Snow M.R., Nitta I., and Tomita K. Acta Cryst. 17 (1964) 1463
42. Nakamoto K. Infrared and Raman Spectra of Inorganic and Coordination Compounds - Part B: Applications in Coordination, Organometallic, and Bioinorganic Chemistry. 5th ed. (1997), Wiley pp. 53, 63, 65
43. Lambie B., Ramaekers R., and Maes G. J. Phys. Chem. 108 (2004) 10426
44. Téllez S C.A., Hollauer E., Mondragón M.A., and Castaño V.M. Spectrochim. Acta A 60 (2004) 2171
45. Téllez C.A., Hollauer E., Mondragón M.A., and Castaño V.M. Spectrochim. Acta A 57 (2001) 993
46. Bellamy L.J., and Williams R.L. Spectrochim Acta 9 (1957) 341
47. 2]. Spectrochim. Acta A 67 3-4 (2007) 1046
48. Ramos J.M., Versiane O., Felcman J., and Téllez S C.A. FT-IR vibrational spectrum and DFT: B3LYP/6-31G structure and vibrational analysis of guanidinoaceticserinenickel (II) complex: [Ni(GAA)(Ser)]. Spectrochim. Acta A 67 3-4 (2007) 1037
49. chemcraft Software .
50. Ozinskas A.J., and Rosenthal G.A. Bioorg. Chem. 14 2 (1986) 157
51. Babu A.S., and Gowda T.V. Toxicon 32 6 (1994) 749
52. Deng J., Hamada Y., and Shioiri T. Tetrahedron Lett. 37 13 (1996) 2261
53. Machuqueiro M., and Darbre T. J. Inorg. Biochem. 94 (2003) 193
54. Wang C.-L., Miyata T., Weksler B., Rubin A.L., and Stenzel K.H. Biochim. Biophys. Acta 544 3 (1978) 555
55. Michel T., Debart F., and Vasseur J.-J. Tetrahedron Lett. 44 35 (2003) 6579
56. Rosenthal G.A., and Harper L. Insect Biochem. Mol. Biol. 26 4 (1996) 389
57. van Boekel M.A.M., and Van Venrooij W.J. Autoimmun. Rev. 2 (2003) 57
58. Huang Y., Komoto1 J., Konishi K., Takata Y., Ogawa H., Gomi T., and Fujioka M. J. Mol. Biol. 298 (2000) 149