Tetranuclear copper(II) complexes bridged by α-D-glucose-1-phosphate and incorporation of sugar acids through the Cu4 core structural changes

Inorganic Chemistry

Volumn 45, Issue 17, 2006, Pages 6646-6660

  Kato, Merii ^a   Sah, Ajay Kumar ^a   Tanase, Tomoaki ^a   Mikuriya, Masahiro ^b  

^a NARA WOMEN'S UNIVERSITY   (Japan)

^b KWANSEI GAKUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID; COPPER; DISACCHARIDE; GLUCOSE 1 PHOSPHATE; GLUCOSE PHOSPHATE; LACTOBIONIC ACID; LIGAND; POLYMER; SACCHARIC ACID; SUGAR ACID;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; ELECTROSPRAY MASS SPECTROMETRY; HYDROGEN BOND; OXIDATION REDUCTION REACTION; STEREOISOMERISM;

CARBOXYLIC ACIDS; CIRCULAR DICHROISM; COPPER; DISACCHARIDES; GLUCARIC ACID; GLUCOSEPHOSPHATES; HYDROGEN BONDING; LIGANDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; POLYMERS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STEREOISOMERISM; SUGAR ACIDS;

EID: 33748624885     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic060202h     Document Type: Article

References (113)

1. (a) He, X.; Agnihotri, G.; Liu, H.-H. Chem. Rev. 2000, 100, 4615.
2. (b) Sträter, N.; Lipscomb, W. N.; Klabunde, T.; Krebs, B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2024.
3. (c) Wilcox, D. E. Chem. Rev. 1996, 96, 2435.
4. (d) Sears, P.; Wong, C.-H. Angew. Chem., Int. Ed. 1999, 38, 2300.
5. (e) Wong, C.-H. Acc. Chem. Res. 1999, 32, 376.
6. (f) Lavie, A.; Allen, K. N.; Petsko, G. A.; Ringe, D. Biochemistry 1994, 33, 5469.
7. (g) Deacon, A.; Gleichmann, T.; Kalb, A. J.; Price, H.; Raftery, J.; Bradbrook, G.; Yariv, J.; Helliwell, J. R. J. Chem. Soc., Faraday Trans. 1997, 93, 4305.
8. (h) Weis, W. I.; Drickamer, K.; Hendrickson, W. A. Nature 1992, 360, 127.
9. (i) Drickamer, K. Nature 1992, 360, 183.
10. (j) Ito, N.; Phillips, S. E. V.; Stevens, C.; Ogel, Z. B.; McPherson, M. J.; Keen, J. N.; Yadav, K. D. S.; Knowles, P. F. Nature 1991, 350, 87.
11. (a) Yano, S. Coord. Chem. Rev. 1988, 92, 113.
12. (b) Yano, S.; Nakagoshi, M.; Teratani, A.; Kato, M.; Onaka, T.; Iida, M.; Tanase, T.; Yamamoto, Y.; Uekusa, H.; Ohashi, Y. Inorg. Chem. 1997, 36, 4187.
13. (c) Tanase, T.; Onaka, T.; Nakagoshi, M.; Kinoshita, I.; Shibata, K.; Doe, M.; Fujii, J.; Yano, S. Inorg. Chem. 1999, 38, 3150.
14. (d) Tanase, T.; Tamakoshi, S.; Doi, M.; Mikuriya, M.; Sakurai, H.; Yano, S. Inorg. Chem. 2000, 39, 692.
15. (e) Tanase, T.; Inukai, H.; Onaka, T.; Kato, M.; Yano, S.; Lippard, S. J. Inorg. Chem. 2001, 40, 3943.
16. (f) Zhang, W.; Jiang, T.; Ren, S.; Zhang, Z.; Guan, H.; Yu, J. Carbohydr. Res. 2004, 339, 2139.
17. (g) Wegner, R.; Gottschaldt, M.; Gorls, H.; Jager, E.-G.; Klemm, D. Chem. - Eur. J. 2001, 7, 2143.
18. (h) Wegner, R.; Gottschaldt, M.; Görls, H.; Jäger, E.-G.; Klemm, D. Angew. Chem., Int. Ed. 2000, 39, 595.
19. (i) Gottschaldt, M.; Wegner, R.; Görls, H.; Klüfers, P.; Jäger, E.-G.; Klemm, D. Carbohydr. Res. 2004, 339, 1941.
20. (a) Sah, A. K.; Kato, M.; Tanase, T. Chem. Commun. 2005, 675. (
21. b) Sah, A. K.; Tanase, T. Chem. Commun. 2005, 5980.
22. (c) Fragoso, A.; Kahn, M. L.; Castineiras, A.; Sutter, J.-P.; Kahn, O.; Cao, R. Chem. Commun. 2000, 1547.
23. (d) Larpent, C.; Laplace, A.; Zemb, T. Angew. Chem., Int. Ed. 2004, 43, 3163.
24. (a) Diéguez, M.; Pàmies, O.; Claver, C. Chem. Rev. 2004, 104, 3189.
25. (b) Castillón, S.; Claver, C.; Díaz, Y. Chem. Soc. Rev. 2005, 34, 702 and references cited therein.
26. (a) Gyurcsik, B.; Nagy, L. Coord. Chem. Rev. 2000, 203, 81.
27. (b) Klüfers, P.; Schuhmacher, J. Angew. Chem. Int. Ed. Engl. 1994, 33, 1742.
28. (c) Klaassen, M.; Klüfers, P. Acta Crystallogr., Sect. C 1994, 50, 686.
29. (d) Klüfers, P.; Schuhmacher, J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2119.
30. (e) Burger, J.; Gack, C.; Klüfers, P. Angew. Chem., Int. Ed. Engl. 1995, 34, 2647.
31. (f) Gack, C.; Klüfers, P. Acta Crystallogr., Sect. C 1996, 52, 2972.
32. (g) Burger, J.; Klüfers, P. Angew. Chem., Int. Ed. 1997, 36, 776.
33. (h) Geisselmann, A.; Klüfers, P.; Pilawa, B. Angew. Chem., Int. Ed. 1998, 37, 1119.
34. (i) Ahlrichs, R.; Ballauff, M.; Eichkorn, K.; Hanemann, O.; Kettenbach, G.; Klüfers, P. Chem. - Eur. J. 1998, 4, 835.
35. (j) Klüfers, P.; Mayer, P. Acta Crystallogr., Sect. C 1998, 54, 583.
36. (k) Klüfers, P.; Kunte, T. Angew. Chem., Int. Ed. 2001, 40, 4210.
37. (l) Klüfers, P.; Kunte, T. Eur. J. Inorg. Chem. 2002, 1285.
38. (m) Klüfers, P.; Krotz, O.; Ossberger, M. Eur. J. Inorg. Chem. 2002, 1919.
39. (n) Klüfers, P.; Kunte, T. Chem. - Eur. J. 2003, 9, 2013.
40. (o) Geisselmann, A.; Klüfers, P.; Kropfgans, C.; Mayer, P.; Piotrowski, H. Angew. Chem., Int. Ed. 2005, 44, 924.
41. (p) Barth, M.; Kästele, X.; Klüfers, P. Eur. J. Inorg. Chem. 2005, 1353.
42. (q) Yang, L.; Su, Y.; Xu, Y.; Wang, Z.; Guo, Z.; Weng, S.; Yan, C.; Zhang, S.; Wu, J. Inorg. Chem. 2003, 42, 5844.
43. (a) Voet, D.; Voet, J. G. Biochemistry, 2nd ed.; John Wiley & Sons: New York, 1995; pp 443-512.
44. (b) Nelson, D. L.; Cox, M. M. Lehninger Principles of Biochemistry, 3rd ed.; Worth Publisher: New York, 2000; pp 527-566 and 722-769.
45. (a) Zhang, Y.; Liang, J.-Y.; Huang, S.; Ke, H.; Lipscomb, W. N. Biochemistry 1993, 32, 1844.
46. (b) Xue, Y.; Huang, S.; Liang, J.-Y.; Zhang, Y.; Lipscomb, W. N. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 12482.
47. (c) Villeret, V.; Huang, S.; Zhang, Y.; Lipscomb, W. N. Biochemistry 1995, 34, 4307.
48. (d) Bone, R.; Frank, L.; Springer, J. P.; Atack, J. R. Biochemistry 1994, 33, 9468.
49. (a) Cleasby, A.; Wonacott, A.; Skarzynski, T.; Hubbard, R. E.; Davies, G. J.; Proudfoot, A. E. I.; Bernard, A. R.; Payton, M. A.; Wells, T. N. C. Nat. Struct. Biol. 1996, 3, 470.
50. (b) Wells, T. N. C.; Coulin, F.; Payton, M. A.; Proudfoot, A. E. I. Biochemistry 1993, 32, 1294.
51. (a) Swan, M. K.; Solomons, J. T. G.; Beeson, C. C.; Hansen, T.; Schonheit, P.; Davies, C. J. Biol. Chem. 2003, 278, 47261.
52. (b) Berrisford, J. M.; Akerboom, J.; Turnbull, A. P.; de Geus, D.; Sedelnikova, S. E.; Staton, I.; McLeod, C. W.; Verhees, C. H.; van der Oost, J.; Rice, D. W.; Baker, P. J. J. Biol. Chem. 2003, 278, 33290.
53. Lahiri, S. D.; Zhang, G.; Dunaway-Mariano, D.; Allen, K. N. Science 2003, 299, 2067.
54. (a) Andersson, I.; Knight, S.; Schneider, G.; Lindqvist, Y.; Lundqvist, T.; Branden, C.-I.; Lorimer, G. H. Nature 1989, 337, 229.
55. (b) Mizohata, E.; Matsumura, H.; Okano, Y.; Kumei, M.; Takuma, H.; Onodera, J.; Kato, K.; Shibata, N.; Inoue, T.; Yokota, A.; Kai, Y. J. Mol. Biol. 2002, 316, 679.
56. (c) Karkehabadi, S.; Taylor, T. C.; Andersson, I. J. Mol. Biol. 2003, 334, 65.
57. (a) Blom, N. S.; Tetreault, S.; Coulombe, R.; Sygusch, J. Nat. Struct. Biol. 1996, 3, 856.
58. (b) Cooper, S. J.; Leonard, G. A.; McSweeney, S. M.; Thompson, A. W.; Naismith, J. H.; Qamar, S.; Plater, A.; Berry, A.; Hunter, W. N. Structure 1996, 4, 1303.
59. (c) Wedekind, J. E.; Frey, P. A.; Rayment, I. Biochemistry 1995, 34, 11049.
60. (d) Koropatkin, N. M.; Holden, H. M. J. Biol. Chem. 2004, 279, 44023.
61. (e) Luo, Y.; Samuel, J.; Mosimann, S. C.; Lee, J. E.; Tanner, M. E.; Strynadka, N. C. J. Biochemistry 2001, 40, 14763.
62. (f) Jelakovic, S.; Kopriva, S.; Suss, K.-H.; Schultz, G. E. J. Mol. Biol. 2003, 326, 127.
63. For example, see: (a) Narendra, N.; Seshadri, T. P.; Viswamitra, M. A. Acta Crystallogr., Sect. C 1984, 40, 1338.
64. (b) Lis, T. Carbohydr. Res. 1985, 135, 187.
65. (c) Narendra, N.; Seshadri, T. P.; Viswamitra, M. A. Acta Crystallogr., Sect. C 1985, 41, 1612.
66. (d) Narendra, N.; Seshadri, T. P.; Viswamitra, M. A. Acta Crystallogr., Sect. C 1985, 41, 31.
67. (a) Pigman, W.; Horton, D. The Carbohydrates. Chemistry and Biochemistry, 2nd ed.; Academic Press: New York, 1980; Vol. IB, pp 1013-1099.
68. (b) Kennedy, J. F.; White, C. A. Bioactive Carbohydrates in Chemistry, Biochemistry and Biology; Ellis Horwood Ltd.; Chichester, England, 1983.
69. (c) Robyt, J. F. Essentials of Carbohydrate Chemistry; Springer-Verlag: New York, 1998.
70. (a) Whitfield, D. M.; Stojkovsky, S.; Sarkar, B. Coord. Chem. Rev. 1993, 122, 171.
71. (b) Sawyer, D. T. Chem. Rev. 1964, 64, 3.
72. (c) T-Riahi, H. A. J. Inorg. Biochem. 1986, 26, 23.
73. (d) Haas, J. W., Jr. Mar. Chem. 1986, 19, 299.
74. (a) Huber, G. W.; Chheda, J. N.; Barrett, C. J.; Dumesic, J. A. Science 2005, 308, 1446.
75. (b) Huber, G. E.; Cortright, R. D.; Dumesic, J. A. Angew. Chem., Int. Ed. 2004, 43, 1549.
76. (c) Mecking, S. Angew. Chem., Int. Ed. 2004, 43, 1078.
77. (d) Cortright, R. D.; Davda, R. R.; Dumesic, J. A. Nature 2002, 418, 964.
78. (e) Danner, H.; Braun, R. Chem. Soc. Rev. 1999, 28, 395.
79. Kato, M.; Tanase, T. Inorg. Chem. 2005, 44, 8.
80. Inoue, M.; Yamase, T. Bull. Chem. Soc. Jpn. 1996, 69, 2863.
81. Ito, M.; Nakazawa, J.; Maeda, K.; Kano, K.; Mizutani, T.; Kodera, M. Inorg. Chem. 2005, 44, 691.
82. Ojida, A.; Mito-oka, Y.; Sada, K.; Hamachi, I. J. Am. Chem. Soc. 2004, 126, 2454.
83. Fry, F. H.; Jensen, P.; Kepert, C. M.; Spiccia, L. Inorg. Chem. 2003, 42, 5637.
84. Gross, F.; Müller-Hartmann, A.; Vahrenkamp, H. Eur. J. Inorg. Chem. 2000, 2363.
85. Kimura, E.; Aoki, S.; Koike, T.; Shiro, M. J. Am. Chem. Soc. 1997, 119, 3068.
86. Otieno, T.; Mokry, L. M.; Bond, M. R.; Carrano, C. J.; Dean, N. S. Inorg. Chem. 1996, 35, 850.
87. (a) Crawford, V. H.; Richardson, H. W.; Wasson, J. R.; Hodgson, D. J.; Hatfield, W. E. Inorg. Chem. 1976, 15, 2107.
88. (b) Ruiz, E.; Alemany, P.; Alvarez, S.; Cano, J. Inorg. Chem. 1997, 36, 3683.
89. Merz, L.; Haase, W. J. Chem. Soc., Dalton Trans. 1980, 875.
90. For example, see: (a) Frutos, A. A.; Escandar, G. M.; Peregrin, J. M. S.; Sierra, M. G.; Sala, L. F. Can. J. Chem. 1997, 75, 405.
91. (b) Escandar, G. M.; Olivieri, A. C.; Sierra, M. G.; Sala, L. F. J. Chem. Soc., Dalton Trans. 1994, 1189.
92. (c) Escandar, G. M.; Sierra, M. G.; Peregrin, J. M. S.; Labadié, G.; Santoro, M.; Frutos, A.; Sala, L. F. Polyhedron 1994, 13, 909.
93. (d) Frutos, A. A.; Signorella, S.; Sala, L. F.; Escandar, G. M.; Peregrin, J. M. S.; Moreno, V. Polyhedron 1998, 17, 3371.
94. (e) González, J. C.; Daier, V.; García, S.; Goodman, B. A.; Atria, A. M.; Sala, L. F.; Signorella, S. J. Chem. Soc., Dalton Trans. 2004, 2288.
95. (f) Roldán, V.; Santoro, M.; González, J. C.; Peregrin, J. M. S.; Signorella, S.; Sala, L. F. J. Inorg. Biochem. 2004, 98, 347.
96. Abrahams, B. F.; Moylan, M.; Orchard, S. D.; Robson, R. Angew. Chem., Int. Ed. 2003, 42, 1848.
97. Kim, K. M.; Song, S. C.; Lee, S. B.; Kang, H. C.; Sohn, Y. S. Inorg. Chem. 1998, 37, 5764.
98. (a) Saladini, M.; Candini, M.; Iacopino, D.; Menabue, L. Inorg. Chim. Acta 1999, 292, 189.
99. (b) Ferrier, F.; Avezou, A.; Terzian, G.; Benlian, D. J. Mol. Struct. 1998, 442, 281.
100. Lis, T. Acta Crystallogr., Sect. B 1979, 35, 1699.
101. (a) Castillo, O.; Muga, I.; Luque, A.; Zorrilla, J. M. G.; Sertucha, J.; Vitoria, P.; Roman, P. Polyhedron 1999, 18, 1235.
102. (b) Tang, J.; Gao, E.; Bu, W.; Liao, D.; Yan, S.; Jiang, Z.; Wang, G. J. Mol. Struct. 2000, 525, 271.
103. Shi, J.-M.; Zhu, S.-C.; Wu, C.-J. Chin. J. Struct. Chem. 2004, 23, 1027.
104. (a) Arts, S. J. H. F.; Mombarg, E. J. M.; van Bekkum, H.; Sheldon, R. A. Synthesis 1997, 597.
105. (b) Ródio, R. T.; Pereira, E. M.; Tavares, M. F. M.; Ferreira, A. M. C. Carbohydr. Res. 1999, 315, 319 and references cited therein.
106. Crystal Clear 1.3.5: Operating Software for the CCD Detector System; Rigaku and Molecular Structure Corp.: Tokyo, Japan, 2003.
107. (a) Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, M.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A.; Polidori, G.; Spagna, R. J. Appl. Crystallogr. 1999, 32, 115.
108. (b) Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, M.; Giacovazzo, C.; Guagliardi, A.; Polidori, G. J. Appl. Crystallogr. 1994, 27, 435.
109. (a) Sheldrick, G. M. SHELXL-93: Program for Crystal Structure Refinement; University of Göttingen: Göttingen, Germany, 1993.
110. (b) Sheldrick, G. M. SHELXL-97: Program for the Refinement of Crystal Structures; University of Göttingen: Göttingen, Germany, 1997.
111. Beurskens, P. T.; Admiraal, G.; Beurskens, G.; Bosman, W. P.; de Gelder, R.; Israel, R.; Smits, J. M. M. DIRDIF-94 Program System; Technical Report of the Crystallography Laboratory; University of Nijmegen: Nijmegen, The Netherlands, 1994.
112. Crystal Structure 3.6: Crystal Structure Analysis Package; Rigaku and Molecular Structure Corp.: Tokyo, Japan, 2003.
113. teXsan: Crystal Structure Analysis Package; Rigaku and Molecular Structure Corp.: Tokyo, Japan, 1999.