Coordination compounds of pteridine, alloxazine and flavin ligands: Structures and properties

Coordination Chemistry Reviews

Volumn 182, Issue 1, 1999, Pages 323-342

  Kaim, Wolfgang ^a   Schwederski, Brigitte ^a   Heilmann, Oliver ^a   Hornung, Fridmann M ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

Author keywords

Chelate coordination; Coenzymes; Flavins; Pteridines; Structures

Indexed keywords

EID: 0033073889     PISSN: 00108545     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0010-8545(98)00193-3     Document Type: Review

References (131)

1. W. Kaim, B. Schwederski, Bioinorganic Chemistry, Wiley, Chichester, 1994.
2. (a) L.G. Marzilli, Adv. Inorg. Biochem. 3 (1981) 47.
3. (b) B. Lippert, BioMetals 5 (1992) 195.
4. D.M. Whitfield, S. Stoijkowski, B. Sarkar, Coord. Chem. Rev. 122 (1993) 171.
5. (a) A. Eschenmoser, Angew. Chem. Int. Ed. Engl. 27 (1988) 5.
6. (b) B. Kräutler, Chimia 41 (1987) 277.
7. B.C. Pressman, in: H. Sigel (Ed.), Metal Ions in Biological Systems, vol. 19, Marcel Dekker, New York, 1985, p. 1.
8. D.M. Bryan, S.D. Pell, R. Kumar, M.J. Clarke, V. Rodriguez, M. Sherban et al., J. Am. Chem. Soc. 110 (1988) 1498 and literature cited therein.
9. (a) M.J. Clarke, Comments Inorg. Chem. 3 (1984) 133.
10. (b) M.J. Clarke, Rev. Inorg. Chem. 2 (1980) 27.
11. P. Hemmerich, C. Veeger, H.C.S. Wood, Angew. Chem. Int. Ed. Engl. 4 (1965) 671.
12. P. Hemmerich, J. Lauterwein, in: G.I. Eichhorn (Ed.), Inorganic Chemistry, Elsevier, Amsterdam, 1973, p. 1168.
13. J. Lauterwein, P. Hemmerich, J.M. Lhoste, Inorg. Chem. 14 (1975) 2152, 2161.
14. H. Beinert, V. Massey, Trends Biol. Sci. (1982) 43.
15. P. Kierkegaard, M. Leijonmarck, P.-E. Werner, Acta Chem. Scand. 26 (1972) 2980.
16. C.J. Fritchie Jr., J. Biol. Chem. 247 (1972) 7459.
17. R.H. Benno, C.R. Fritchie Jr., Acta Cryst. Sect. B 29 (1973) 2493.
18. T.D. Wade, C.R. Fritchie Jr., J. Biol. Chem. 248 (1973) 2337.
19. C.J. Fritchie Jr., J. Biol. Chem. 248 (1973) 7516.
20. W.T. Garland, C.J. Fritchie Jr., J. Biol. Chem. 249 (1974) 2228.
21. M.W. Yu, C.J. Fritchie Jr., J. Biol. Chem. 250 (1975) 946.
22. M.W. Yu and C.J. Fritchie Jr., J. Chem. Soc., Dalton Trans. (1975) 377.
23. M.J. Clarke, M.G. Dowling, A.R. Garafalo, T.F. Brennan, J. Am. Chem. Soc. 101 (1979) 223.
24. M.J. Clarke, M.G. Dowling, A.R. Garafalo, T.F. Brennan, J. Biol. Chem. 255 (1980) 3472.
25. S.J.N. Burgmayer, E.I. Stiefel, J. Am. Chem. Soc. 108 (1986) 8310.
26. S.J.N. Burgmayer, E.I. Stiefel, Inorg. Chem. 27 (1988) 4059.
27. T. Kohzuma, H. Masuda, O. Yamauchi, J. Am. Chem. Soc. 111 (1989) 3431.
28. (a) O. Yamauchi, A. Odani, H. Masuda, Y. Funahashi, in: K.D. Karlin, Z. Tyeklár (Eds.), Bioinorganic Chemistry of Copper, Chapman and Hall, New York, 1993, p. 363.
29. (b) O. Yamauchi, Pure Appl. Chem. 67 (1995) 297.
30. J. Perkinson, S. Brodie, K. Yoon, K. Mosny, P.J. Carroll, T. Vance Morgan, et al., Inorg. Chem. 30 (1991) 719.
31. B. Fischer, J. Strähle, M. Viscontini, Helv. Chim. Acta 74 (1991) 1544.
32. B. Fischer, J. Strähle, M. Viscontini, Pteridines 3 (1992) 91.
33. B. Fischer, H.W. Schmalle, E. Dubler, A. Schäfer, M. Viscontini, Inorg. Chem. 34 (1995) 5726.
34. B. Fischer, H.W. Schmalle, M.R. Baumgartner, M. Viscontini, Helv. Chim. Acta 80 (1997) 103.
35. M. Mitsumi, J. Toyoda, K. Nakasuji, Inorg. Chem. 34 (1995) 3367.
36. S.J.N. Burgmayer, M.R. Arkin, L. Bostick, S. Dempster, K.M. Everett, H.L. Layton, et al., J. Am. Chem. Soc. 117 (1995) 5812.
37. Y. Funahashi, Y. Hara, H. Masuda, O. Yamauchi, Inorg. Chem. 36 (1997) 3869.
38. D.H. Lee, N.N. Murthy, Y. Lin, N.S. Nasir, K.D. Karlin, Inorg. Chem. 36 (1997) 6328.
39. (a) R. Hille, Chem. Rev. 96 (1996) 2757.
40. (b) R. Collison, C.D. Garner, J.A. Joule, Chem. Soc. Rev. 25 (1996) 25.
41. (c) D.C. Rees, Y. Hju, C. Kisker, H. Schindelin, J. Chem. Soc., Dalton Trans. (1997) 3909.
42. (d) E.I. Stiefel, J. Chem. Soc., Dalton Trans. (1997) 3915.
43. (e) E.S. Davies, R.L. Beddoes, D. Collison, A. Dinsmore, A. Docrat, J.A. Joule, et al., J. Chem. Soc., Dalton Trans. (1997) 3985.
44. (f) S.D. Garton, J. Hilton, H. Oku, B.R. Crouse, K.V. Rajagopalan, M.K. Johnson, J. Am. Chem. Soc. 119 (1997) 12906.
45. (g) B.L. Westcott, N.E. Gruhn, J.H. Enemark, J. Am. Chem. Soc. 120 (1998) 3382.
46. (a) S.J. Benkovic, R.L. Blakeley (Eds.), Folates and Pterins: Vol. 2, Chemistry and Biochemistry of Pterins, Wiley, New York, 1985.
47. (b) B.A. Copper, V.M. Whitehead (Eds.), Chemistry and Biology of Pteridines and Folic Acid Derivates, de Gruyter, Berlin, 1986.
48. (c) T.A. Dix, S.J. Benkovic, Acc. Chem. Res. 21 (1988) 101.
49. (d) T.J. Kappock, J.P. Caradonna, Chem. Rev. 96 (1996) 2659.
50. (e) K.E. Goodwill, C. Sabatier, C. Marks, R. Raag, P.F. Fitzpatrick, R.C. Stevens, Nat. Struct. Bio. 4 (1997) 578.
51. S.J.N. Burgmayer, Struct. Bonding (Berlin) 92 (1998).
52. (a) P. Hemmerich, V. Massey, H. Michel, C. Schug, Struct. Bonding (Berlin) 48 (1982) 93.
53. (b) F. Müller (Ed.), Chemistry and Biochemistry of Flavoenzymes, CRC Press, Boca Raton, 1991.
54. (c) S. Ghisla, V. Massey, Eur. J. Biochem. 181 (1989) 1.
55. (d) C.T. Walsh, Acc. Chem. Res. 13 (1980) 148 and 19 (1986) 216.
56. (d) C.T. Walsh, Acc. Chem. Res. 13 (1980) 148 and 19 (1986) 216.
57. W. Kaim, Rev. Chem. Intermed. 8 (1987) 247 and literature cited.
58. W. Kaim, A. Schulz, F. Hilgers, H.-D. Hausen, M. Moscherosch, A. Lichtblau, et al., Res. Chem. Intermed. 19 (1993) 603.
59. (a) A. Ehrenberg, Vitam. Horm. (New York) 28 (1970) 489.
60. (b) D.E. Edmondson, G. Tollin, Top. Curr. Chem. 108 (1983) 109.
61. (c) G. Eberlein, T.C. Bruice, J. Am. Chem. Soc. 105 (1983) 6658.
62. B.R. Crane, A.S. Arvai, D.K. Ghosh, C. Wu, E.D. Getzoff, D.J. Stuehr, et al., Science 279 (1998) 2121.
63. (a) W. Pfleiderer, in: S.J. Benkovic, R.L. Blakeley (Eds.), Chemistry and Biochemistry of Pterins, vol. 2, Wiley, Chichester, 1985, p. 43.
64. (b) W. Pfleiderer, J. Heterocycl. Chem. 29 (1992) 583.
65. (a) R.L. Blakeley, The Biochemistry of Folic Acid and Related Pteridines, North Holland, Amsterdam, 1963.
66. (b) J.E. Ayling, M.G. Nair, C.M. Baugh (Eds.), Chemistry and Biology of Pteridines and Folates, Plenum Press, New York, 1993.
67. O.W. Griffith, D.J. Stuehr, Annu. Rev. Physiol. 57 (1995) 707.
68. S.P. Greatbanks, I.H. Hillier, C.D. Garner, J.A. Joule, J. Chem. Soc., Perkin Trans. 2 (1997) 1529.
69. D.W. Young, Chem. Soc. Rev. 23 (1994) 119.
70. (a) R.H. Holm, Chem. Rev. 87 (1987) 1401.
71. (b) R.H. Holm, Coord. Chem. Rev. 100 (1990) 183.
72. (c) C. Lorber, M.R. Plutino, L.I. Elding, E. Nordlander, J. Chem. Soc., Dalton Trans. (1997) 3997.
73. E.I. Stiefel, D. Coucouvanis, W.E. Newton (Eds.), Molybdenum Enzymes, Cofactors and Model Systems, ACS-Symposium Series 535, Washington, 1993.
74. S. Mukund, M.W.W. Adams, J. Biol. Chem. 268 (1993) 13592.
75. M.K. Chan, S. Mukund, A. Kletzin, M.W.W. Adams, D.C. Rees, Science 267 (1995) 1463.
76. J. Romao, M. Archer, I. Moura, J.J.G. Moura, J. LeGall, R. Engh, et al., Science 270 (1995) 1170.
77. (a) H. Schindelin, C. Kisker, J. Hilton, K.V. Rajagopalan, D.C. Rees, Science 272 (1996) 1615.
78. (b) E.I. Stiefel, Science 272 (1996) 1599.
79. (c) J.C. Boyington, V.N. Gladyshev, S.V. Khangulov, T.C. Stadtman, P.D. Sun, Science 275 (1997) 1305.
80. R.T. Carr, S. Balasubramanian, P.C.D. Hawkins, S.J. Benkovic, Biochemistry 34 (1995) 7525.
81. J. Lee, D.J. O'Kane, A.J.W.G. Visser, Biochemistry 24 (1985) 1476.
82. C. Bessenbacher, S. Ernst, S. Kohlmann, W. Kaim, V. Kasack, E. Roth, et al. J. Chem. Soc., Faraday Trans. 1, 85 (1989) 4075.
83. C. Bessenbacher, C. Vogler, W. Kaim, Inorg. Chem. 28 (1989) 4645.
84. (a) A. Juris, V. Balzani, F. Barigelletti, S. Campagna, P. Belser, A. von Zelewsky, Coord. Chem. Rev. 84 (1988) 85.
85. (b) E.C. Constable, Adv. Inorg. Chem. 34 (1989) 1.
86. S. Greulich, W. Kaim, A. Stange, H. Stoll, J. Fiedler, S. Zalis, Inorg. Chem. 35 (1996) 3998.
87. (a) R.P. Burns, C.A. McAuliffe, Adv. Inorg. Chem. Radiochem. 22 (1979) 303.
88. (b) K.R. Barnard, A.G. Wedd, E.R.T. Tiekink, Inorg. Chem. 29 (1990) 8.
89. M.J. Clarke, M.G. Dowling, Inorg. Chem. 20 (1981) 3506.
90. M.G. Dowling, M.J. Clarke, Inorg. Chim. Acta 78 (1983) 153.
91. (a) M. Wrighton, D.L. Morse, J. Am. Chem. Soc. 96 (1974) 998.
92. (b) D.P. Summers, J.C. Luong, M.S. Wrighton, J. Am. Chem. Soc. 103 (1981) 5238.
93. (c) W. Kaim, S. Kohlmann, Inorg. Chem. 29 (1990) 2909.
94. B. Schwederski, W. Kaim, Inorg. Chim. Acta 195 (1992) 123.
95. C. Bessenbacher, W. Kaim, Z. Anorg. Allg. Chem. 577 (1989) 39.
96. H. Kunkely, A. Vogler, Z. Naturforsch. 536 (1998) 423.
97. A.N. Singh, E. Gelerinter, E.S. Gould, Inorg. Chem. 21 (1982) 1232.
98. O. Heilmann, H.-D. Hausen, W. Kaim, Z. Naturforsch. 49b (1994) 1554.
99. O. Heilmann, F.M. Hornung, W. Kaim, J. Fiedler, J. Chem. Soc., Faraday Trans. 92 (1996) 4233.
100. F. Hueso-Ureña, S.B. Jiménez-Pulido, M.N. Moreno-Carretero, M. Quirós-Olozábal, J.M. Salas-Peregrín, Polyhedron 16 (1997) 607.
101. F. Hueso-Ureña, S.B. Jiménez-Pulido, M.N. Moreno-Carretero, M. Quirós-Olozábal, J.M. Salas-Peregrín, Inorg. Chim. Acta 268 (1998) 77.
102. F. Huesco-Ureña, S.B. Jiménez-Pulido, M.N. Moreno-Carretero, M. Quirós-Olozábal, J.M. Salas-Peregrín, Inorg. Chim. Acta 277 (1998) 103.
103. F. Hornung, W. Kaim, J. Chem. Soc., Faraday Trans. 90 (1994) 2909.
104. O. Heilmann, Ph.D. thesis, Universität Stuttgart, 1997
105. F. Hornung, Ph.D. thesis, Universität Stuttgart, 1997.
106. J. Selbin, J. Sherrill, C.H. Bigger, Inorg. Chem. 13 (1974) 2544.
107. S. Shinkai, H. Nakao, N. Honda, O. Manabe, F. Mueller, J. Chem. Soc., Perkin Trans, 1 (1986) 1825.
108. S. Shinkai, Y. Ishikawa, O. Manabe, Bull. Chem. Soc. Jpn. 56 (1983) 1694.
109. S. Shinkai, N. Hideki, K. Ueda, O. Manabe, Tetrahedron Lett. 25 (1984) 5295.
110. S. Fukuzumi, S. Kuroda, T. Toshio, J. Am. Chem. Soc. 107 (1985) 3020.
111. Y. Yano, T. Sakaguchi, M. Nakazato, J. Chem. Soc., Perkin Trans. 2 (1984) 595.
112. S. Shinkai, N. Honda, Y. Ishikawa, O. Manabe, J. Chem. Soc., Perkin Trans. 1 (1985) 565.
113. S. Bhattacharya, S.R. Boone, C.G. Pierpont, J. Am. Chem. Soc. 112 (1990) 4561.
114. K.J. Black, H. Huang, S. High, L. Starks, M. Olson, M.E. McGuire, Inorg. Chem. 32 (1993) 5591.
115. H. Sigel, B. Song, G. Liang, R. Halbach, M. Felder, M. Bastian, Inorg. Chim. Acta 240 (1995) 313.
116. C. Bessenbacher, W. Kaim, J. Organomet. Chem. 369 (1989) 83.
117. M. Goodgame, M.A. Schmidt, Inorg. Chim. Acta 36 (1979) 151.
118. M. Goodgame, K.W. Johns, Inorg. Chim. Acta 37 (1979) 559.
119. M. Goodgame, K.W. Johns, Inorg. Chim. Acta 34 (1979) 1.
120. A. Odani, H. Masuda, K. Inukai, O. Yamauchi, J. Am. Chem. Soc. 114 (1992) 6294.
121. (a) W. Kaim, R. Reinhardt, J. Fiedler, Angew. Chem. 109 (1997) 2600; Angew. Chem. Int. Ed. Engl. 36 (1997) 2493.
122. (a) W. Kaim, R. Reinhardt, J. Fiedler, Angew. Chem. 109 (1997) 2600; Angew. Chem. Int. Ed. Engl. 36 (1997) 2493.
123. (b) W. Kaim, R. Reinhardt, E. Waldhör, J. Fiedler, J. Organomet. Chem. 524 (1996) 195.
124. A. Abelleira, R.D. Galang, M.J. Clarke, Inorg. Chem. 29 (1990) 633.
125. S.J.N. Burgmayer, A. Baruch, K. Kerr, K. Yoon, J. Am. Chem. Soc. 111 (1989) 4982.
126. T. Kohzuma, A. Odani, Y. Morita, M. Takani, O. Yamauchi, Inorg. Chem. 27 (1988) 3854.
127. R.S. Pilato, K.A. Eriksen, M.A. Greaney, E.I. Stiefel, S. Goswami, L. Kilpatrick, et al., J. Am. Chem. Soc. 113 (1991) 9372.
128. (a) M.S. Nasir, K.D. Karlin, Q. Chen, J. Zubieta, J. Am. Chem. Soc. 114 (1992) 2264.
129. (b) B. Fischer, M. vom Orde, K. Leidenberger, A. Pacheco, L. Bigler, Chem. Biol. Pteridines, in: W. Pfleiderer, H. Rokos (Eds.), Proceedings of the 11th International Symposium on Pteridines and Folates, Blackwell Science, Berlin, 1997, p. 23.
130. (a) B. Fischer, J.H. Enemark, P. Basu, J. Inorg. Biochem. (in print).
131. (b) K. Leidenberger, M. vom Orde, B. Fischer, M.-A. Kopf, D.-H. Lee and K.D. Karlin, Biol. Pteridines, in: W. Pfleiderer, H. Rokos (Eds.), Proceedings of the 11th International Symposium on Pteridines and Folates, Blackwell Science, Berlin, 1997, p. 61.