Advertisement

Characterization of High-Valent Oxo-Metalloporphyrins

  • Yoshihito Watanabe
  • Hiroshi Fujii
Chapter
Part of the Structure and Bonding book series (STRUCTURE, volume 97)

Abstract

High-valent oxo metalloporphyrins have been known as reactive intermediates in the catalytic cycles of many heme enzymes and in the oxidation reactions mediated by synthetic metalloporphyrins. In this review, we survey studies of high-valent oxo metalloporphyrins in the past decade. In Sect. 2, electronic structures and magnetic properties of compound I and compound II species in various heme enzymes are discussed on the basis of recent studies of synthetic model complexes of the compound I and compound II. In Sect. 3, spectroscopic properties of oxo manganese porphyrin complexes and their application to biological systems are summarized. In the Sects. 4 and 5, synthesis and characterization of oxo chromium and oxo ruthenium porphyrin complexes are reviewed. In the last section, we have summarized the synthesis and characterization of Mo, Nb, Ti, and V oxo metalloporphyrins complexes.

Keywords

Cytochrome P450 Peroxidase Heme Oxo Metalloporphyrin 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Dawson JH, Sono M (1987) Chem Rev 87: 1255CrossRefGoogle Scholar
  2. 2.
    Watanabe Y, Groves JT (1992) Molecular mechanism of oxygen activation by cytochrome P-450. In: Boyer PD, Sigman DS (eds) The Enzymes, Academic Press, New York, vol 20, p 405Google Scholar
  3. 3.
    Ortiz de Montellano PR (1986) Cytochrome P450, 2nd edn. Plenum Press, New YorkGoogle Scholar
  4. 4.
    Dunford HB (1999) Heme Peroxidases, Wiley-VCH, New York, Chap 4Google Scholar
  5. 5.
    Everse J, Everse KE, Grisham MB (1991) Peroxidases in Chemistry and Biology, CRC Press, Boca Raton, vol I, IIGoogle Scholar
  6. 6.
    Shapiro S, Caspi E (1998) Tetrahedron54: 5005CrossRefGoogle Scholar
  7. 7.
    Guengerich FP, Macdonald TL (1993) Sequential Electron Transfer Reactions Catalyzed by Cytochrome P-450 Enzymes. In: Advances in Electron Transfer Chemistry, vol 3, JAI Press, p 191Google Scholar
  8. 8.
    Mansuy D, Battioni P (1993) Dioxygen Activation at Heme Centers in Enzymes and Synthetic Analogs. In: Reedijk J (ed) Bioinorganic Catalysis, Marcel Dekker, New York, Chap 12, p 395Google Scholar
  9. 9.
    Gunsalus IC, Wagner GC (1978) Bacterial P-450cam Methylene Monooxygenase Components: Cytochrome m, Putidaredoxin, and Putidaredoxin Reductase. In: Fleischer S, Packer L (eds) Methods in Enzymology, Academic Press, New York, vol 52, p166Google Scholar
  10. 10.
    Tabushi I, Koga N (1979) Tetrahedron Lett 3681Google Scholar
  11. 11.
    Tabushi I, Koga N (1978) Tetrahedron Lett 5017Google Scholar
  12. 12.
    Tabushi I, Koga N (1979) J Am Chem Soc101: 6456CrossRefGoogle Scholar
  13. 13.
    Felton RH, Owen GS, Dolphin D, Faier J (1971) J Am Chem Soc93: 6332CrossRefGoogle Scholar
  14. 14.
    Groves JT, Nemo TE, Myers RS (1979) J Am Chem Soc101: 1032CrossRefGoogle Scholar
  15. 15.
    Chang CK, Kuo M-S (1979) J Am Chem Soc101: 3413CrossRefGoogle Scholar
  16. 16.
    Matsuura T (1977) Tetrahedron33: 2869CrossRefGoogle Scholar
  17. 17.
    Gunter MJ, Turner P (1991) Coord Chem Rev 108: 115CrossRefGoogle Scholar
  18. 18.
    Meunier B (1992) Chem Rev92: 1411CrossRefGoogle Scholar
  19. 19.
    Sheldon RA (1994) Metalloporphyrins in Catalytic Oxidations, Marcel Dekker, New YorkGoogle Scholar
  20. 20.
    Collman JP, Zhang X, Lee VJ, Uffelman ES, Braaauman JI (1993) Science261: 1404CrossRefGoogle Scholar
  21. 21.
    Watanabe Y (1997) Model Studies on Heme Monooxygenases. In: Funabiki T (ed) Oxygenases and Model Systems, Kluwer Academic Publishers, Netherlands, vol 19, p 223Google Scholar
  22. 22.
    Dunford HB (1982) Adv Inorg Biochem 4: 41Google Scholar
  23. 23.
    Blumberg WE, Peisach J, Wittenberg BA, Wittenberg AB (1968) J Biol Chem 243: 1854Google Scholar
  24. 24.
    Wolberg A, Manassen J (1970) J Am Chem Soc92: 2982CrossRefGoogle Scholar
  25. 25.
    Moss TH, Ehrenberg A, Bearden AJ (1969) Biochemistry 8: 4159CrossRefGoogle Scholar
  26. 26.
    Fajer J, Borg DC, Forman A, Felton RH, Vegh L, Dolphin D (1973) Ann NY Acad Sci 206: 349CrossRefGoogle Scholar
  27. 27.
    Loew G, Herman ZS (1980) J Am Chem Soc102: 6173CrossRefGoogle Scholar
  28. 28.
    Dolphin D, Forman A, Borg DC, Fajer J, Felton RH (1971) Proc Natl Acad Sci USA 68: 614CrossRefGoogle Scholar
  29. 29.
    Sandusky PO, Salehi A, Chang CK, Babcock GT (1989) J Am Chem Soc111: 6437CrossRefGoogle Scholar
  30. 30.
    Palaniappan V, Terner J (1989) J Biol Chem 264: 16046Google Scholar
  31. 31.
    Fujii H (1993) J Am Chem Soc115: 4641CrossRefGoogle Scholar
  32. 32.
    Schulz CE, Devaney PW, Winkler H, Debrunner PG, Doan N, Chiang R, Rutter R, Hager LP (1979) FEBS Lett 103: 102CrossRefGoogle Scholar
  33. 33.
    Schulz CE, Rutter R, Sage JT, Debrunner PG, Hager LP (1984) Biochemistry 23: 4743CrossRefGoogle Scholar
  34. 34.
    Morishima I, Ogawa S (1978) J Am Chem Soc100: 7125CrossRefGoogle Scholar
  35. 35.
    La Mar G, de Ropp JS (1980) J Am Chem Soc102: 395CrossRefGoogle Scholar
  36. 36.
    Thanabal V, La Mar G, de Ropp JS (1988) Biochemistry 27: 5400CrossRefGoogle Scholar
  37. 37.
    Roberts JE, Hoffman BM, Rutter R, Hager LP (1981) J Biol Chem 256: 2118Google Scholar
  38. 38.
    Roberts JE, Hoffman BM (1981) J Am Chem Soc103: 7654CrossRefGoogle Scholar
  39. 39.
    Penner-Hahn JE, Ebel KS, McMurry TJ, Renner M, Balch AL, Groves JT, Dawson JH, Hodgson KO (1986) J Am Chem Soc108: 7819CrossRefGoogle Scholar
  40. 40.
    Hashimoto S, Tatsuno Y, Kitagawa T (1986) Proc Natl Acad Sci USA 82: 2417CrossRefGoogle Scholar
  41. 41.
    Ogura T, Kitagawa T (1987) J Am Chem Soc109: 2177CrossRefGoogle Scholar
  42. 42.
    Paeng K-J, Kincaid JR (1988) J Am Chem Soc110: 7913CrossRefGoogle Scholar
  43. 43.
    Chuang W-J, Van Wart HE (1992) J Biol Chem 267: 13293Google Scholar
  44. 44.
    Yonetani T, Chance B, Kajiwara S (1966) J Biol Chem 241: 2981Google Scholar
  45. 45.
    Yonetani T (1976) The Enzymes, Academic Press, New York, vol 13Google Scholar
  46. 46.
    Yonetani T, Schleyer H, Ehrenberg A (1966) J Biol Chem 241: 3240Google Scholar
  47. 47.
    Lang G, Spartalian K, Yonetani T (1976) Biochim Biophys Acta 451: 250Google Scholar
  48. 48.
    Sivaraja M, Goodin, DB, Smith M, Hoffman BM (1989) Science245: 738CrossRefGoogle Scholar
  49. 49.
    Hashimoto S, Teraoka J, Inubushi T, Yonetani T, Kitagawa T (1986) J Biol Chem 261: 11110Google Scholar
  50. 50.
    Reczek CM, Sitter AJ, Terner J (1989) J Mol Struct 214: 27CrossRefGoogle Scholar
  51. 51.
    Palcic MM, Rutter R, Araiso T, Hager LP, Dunford HB (1980) Biochem Biophys Res Comm 94: 1123CrossRefGoogle Scholar
  52. 52.
    Rutter R, Hager LP, Dhonau H, Hendrich M, Valentine M, Debrunner P (1984) Biochemistry 23: 6809CrossRefGoogle Scholar
  53. 53.
    Egawa T, Miki H, Ogura T, Makino R, Ishimura I, Kitagawa T (1992) FEBS Lett 305: 206CrossRefGoogle Scholar
  54. 54.
    Schonbaum GR, Chance B (1976) The Enzymes. Academic Press, New York, vol 13Google Scholar
  55. 55.
    Jones P, Middlemiss DN (1972) Biochem J 130: 411Google Scholar
  56. 56.
    Chance B (1949) J Biol Chem 180: 947Google Scholar
  57. 57.
    Gouet P, Jouve H-M, Williams PA, Anderson I, Andreoletti P, Nussaume L, Hajdu J (1996) Nature Struct Biol 3: 951CrossRefGoogle Scholar
  58. 58.
    Benecky MJ, Frew JE, Scowen N, Jones P, Hoffman BM (1993) Biochemistry 32: 11929CrossRefGoogle Scholar
  59. 59.
    Ivancich A, Jouve HM, Sartor B, Gaillard J (1997) Biochemistry 36: 9356CrossRefGoogle Scholar
  60. 60.
    Chuang W-J, Heldt J, Van Wart HE (1989) J Biol Chem 264: 14209Google Scholar
  61. 61.
    Malmstrom BG (1990) Chem Rev90: 1247CrossRefGoogle Scholar
  62. 62.
    Kitagawa T, Ogura T (1997) Progress in Inorganic Chemistry. Karlin KD (Ed), Wiley, vol 45: 431Google Scholar
  63. 63.
    Morgan JE, Verkhovsky MI, Wikström (1996) Biochemistry 35: 12235CrossRefGoogle Scholar
  64. 64.
    Ogura T, Takahashi S, Hirota S, Sinzawa-Itoh K, Yoshikawa S, Kitagawa T (1993) J Am Chem Soc 115: 8527CrossRefGoogle Scholar
  65. 65.
    Groves JT, Haushalter RC, Nakamura M, Nemo TE, Evans BJ (1981) J Am Chem Soc 103: 2884CrossRefGoogle Scholar
  66. 66.
    Mandon D, Weiss R, Jayaraj K, Gold A, Terner J, Bill E, Trautwein AX (1992) Inorg Chem 31: 4404CrossRefGoogle Scholar
  67. 67.
    Penner-Hahn JE, Eble KS, McMurry TJ, Renner M, Balch AL, Groves JT, Dawson JH, Hodgson KO (1986) J Am Chem Soc108: 7819CrossRefGoogle Scholar
  68. 68.
    Hashimoto S, Tatsuno Y, Kitagawa T (1987) J Am Chem Soc109: 8096CrossRefGoogle Scholar
  69. 69.
    Hashimoto S, Mizutani Y, Tatsuno Y, Kitagawa T (1991) J Am Chem Soc114: 6542CrossRefGoogle Scholar
  70. 70.
    Kincaid JR, Schneider AJ, Paeng K-J (1989) J Am Chem Soc111: 735CrossRefGoogle Scholar
  71. 71.
    Groves JT, Watanabe Y (1986) J Am Chem Soc108: 7834CrossRefGoogle Scholar
  72. 72.
    Groves JT, Watanabe Y (1988) J Am Chem Soc110: 8443CrossRefGoogle Scholar
  73. 73.
    Groves JT, Watanabe Y (1986) J Am Chem Soc108: 7836CrossRefGoogle Scholar
  74. 74.
    Yamaguchi K, Watanabe Y, Morishima I (1992) J Chem Soc, Chem Commun 1709Google Scholar
  75. 75.
    Yamaguchi K, Watanabe Y, Morishima I (1993) J Am Chem Soc115: 4058CrossRefGoogle Scholar
  76. 76.
    Dolphin D, Trayler TG, Xie LY (1997) Acc Chem Rev 30: 251CrossRefGoogle Scholar
  77. 77.
    Sugimoto H, Tung H-C, Sawyer DT (1988) J Am Chem Soc110: 2465CrossRefGoogle Scholar
  78. 78.
    Bill E, Ding X-Q, Bominaar EL, Trautwein AX, Winkler H, Mandon D, Weiss R, Gold A, Jayaraj K, Hatfield WE, Kirk M (1990) Eur J Biochem 188: 665CrossRefGoogle Scholar
  79. 79.
    Fujii H, Yoshimura T, Kamada H (1996) Inorg Chem 35: 2373CrossRefGoogle Scholar
  80. 80.
    Fujii H (1994) Chem Lett 1491Google Scholar
  81. 81.
    Fujii H (1993) Inorg Chem 32: 1993CrossRefGoogle Scholar
  82. 82.
    Fujii H, Ichikawa K (1992) Inorg Chem 31: 1110CrossRefGoogle Scholar
  83. 83.
    Czarnecki K, Proniewicz LM, Fujii H, Kincaid J (1996) J Am Chem Soc118: 4680CrossRefGoogle Scholar
  84. 84.
    Czarnecki K, Nimri S, Gross Z, Proniewicz LM, Kincaid J (1996) J Am Chem Soc118: 2929CrossRefGoogle Scholar
  85. 85.
    Gross Z, Nimri S (1994) Inorg Chem 33: 1731CrossRefGoogle Scholar
  86. 86.
    Czarnecki K, Kincaid J, Fujii H (1999) J Am Chem Soc121: 7953CrossRefGoogle Scholar
  87. 87.
    Fujii H, Yoshimura T, Kamada H (1997) Inorg Chem 36: 6142CrossRefGoogle Scholar
  88. 88.
    Collman JP, Sorrell TN, Hoffman BM (1975) J Am Chem Soc97: 914CrossRefGoogle Scholar
  89. 89.
    Ogoshi H, Sugimoto H, Yoshida Z (1975) Tetrahedron Lett: 2289Google Scholar
  90. 90.
    Higuchi T, Uzu S, Hirobe M (1990) J Am Chem Soc112: 7051CrossRefGoogle Scholar
  91. 91.
    Aissaoui H, Ghirlanda S, Gmür C, Woggon W-D (1996) J Mol Cat 113: 393CrossRefGoogle Scholar
  92. 92.
    Volz H, Holzbecher M (1997) Angew Chem Int Ed Engl 36: 1142CrossRefGoogle Scholar
  93. 93.
    Wagenknecht H-A, Woggon W-D (1997) Angew Chem Int Ed Engl 36: 390CrossRefGoogle Scholar
  94. 94.
    Jacob GS, Orme-Johnson WH (1979) Biochemistry 18: 2967CrossRefGoogle Scholar
  95. 95.
    Ozawa S, Watanabe Y, Morishima I (1994) J Am Chem Soc116: 5832CrossRefGoogle Scholar
  96. 96.
    Jayaraj K, Gold A, Austin RN, Mandon D, Weiss R, Tenner J, Bill E, Müther M, Trautwein AX (1995) J Am Chem Soc117: 9079CrossRefGoogle Scholar
  97. 97.
    Yamaguchi K, Watanabe Y, Morishima I (1992) J Cjem Soc Chem Comm 1721Google Scholar
  98. 98.
    Murakami T, Yamaguchi K, Watanabe Y, Morishima I (1998) Bull Chem Soc Jpn 71: 1343CrossRefGoogle Scholar
  99. 99.
    Groves JT, Watanabe Y (1986) J Am Chem Soc108: 7836CrossRefGoogle Scholar
  100. 100.
    Groves JT, Watanabe Y (1988) J Am Chem Soc110: 8443CrossRefGoogle Scholar
  101. 101.
    Mizutani Y, Watanabe Y, Kitagawa T (1994) J Am Chem Soc116: 3439CrossRefGoogle Scholar
  102. 102.
    Tsurumaki H, Watanabe Y, Morishima I (1993) J Am Chem Soc115: 11784CrossRefGoogle Scholar
  103. 103.
    Balch AL, Chan Y-W, Cheng R-J, La Mar GN, Latos-Grazynski L, Renner MW (1984) J Am Chem Soc 106: 7779CrossRefGoogle Scholar
  104. 104.
    Chin DH, Balch AL, La Mar GN (1980) J Am Chem Soc102: 1446CrossRefGoogle Scholar
  105. 105.
    Chin DH, La Mar GN, Balch AL (1980) J Am Chem Soc102: 5945CrossRefGoogle Scholar
  106. 106.
    Groves JT, Gross Z, Stern MK (1994) Inorg Chem 33: 5065CrossRefGoogle Scholar
  107. 107.
    Phillippi MA, Goff HM (1982) J Am Chem Soc104: 6026CrossRefGoogle Scholar
  108. 108.
    Caldewood TS, Lee WA, Bruice TC (1985) J Am Chem Soc107: 8273CrossRefGoogle Scholar
  109. 109.
    Lee WA, Calderwood TS, Bruice TC (1985) Proc Natl Acad Sci USA 82: 4301CrossRefGoogle Scholar
  110. 110.
    Groves JT, Gilbert JA (1986) Inorg Chem 25: 123CrossRefGoogle Scholar
  111. 111.
    Swistak C, Mu XH, Kadish KM (1987) Inorg Chem 26: 4360CrossRefGoogle Scholar
  112. 112.
    Low DW, Winkler JR, Gray HB (1996) J Am Chem Soc118: 117CrossRefGoogle Scholar
  113. 113.
    Hamachi I, Tsukiji S, Shinkai S, Oishi S (1999) J Am Chem Soc121: 5500CrossRefGoogle Scholar
  114. 114.
    Walling C (1975) Acc Chem Rev 8: 125CrossRefGoogle Scholar
  115. 115.
    Poulos TL, Kraut J (1980) J Biol Chem 255: 8199Google Scholar
  116. 116.
    Erman JE, Vitello LB, Miller MA, Kraut J (1992) J Am Chem Soc114: 6592CrossRefGoogle Scholar
  117. 117.
    Erman JE, Vitello LB, Miller MA, Shaw A, Brown KA, Kraut J (1993) Biochemistry 32: 9798CrossRefGoogle Scholar
  118. 118.
    Imai M, Shimada H, Watanabe Y, Matsushima-Hibiya Y, Makino R, Koga H, Horiuchi T, Ishimura Y (1989) Proc Natl Acad Sci USA 86: 7823CrossRefGoogle Scholar
  119. 119.
    Martinis SA, Atkins WM, Stayton PS, Sligar SG (1989) J Am Chem Soc111: 9252CrossRefGoogle Scholar
  120. 120.
    Shimada H, Sligar SG, Yeom H, Ishimura Y (1997) Heme Monooxygenase. In: Funabiki T (ed) Oxygenases and Model Systems, Kluwer Academic Publishers, Netherlands, pp 195–221Google Scholar
  121. 121. (a)
    Crane BR, Arvai AS, Ghosh DK, Wu C, Getzoff ED, Stuehr DJ, Tainer JA (1998) Science 279: 2121CrossRefGoogle Scholar
  122. 121. (b)
    Crane BR, Arvai AS, Gachhui R, Wu C, Ghosh DK, Getzoff ED, Stuehr DJ, Tainer JA (1997) Science278: 425CrossRefGoogle Scholar
  123. 122.
    Quillin ML, Arduini RM, Olson JS, Phillips GN Jr (1993) J Mol Biol 234: 140CrossRefGoogle Scholar
  124. 123. (a)
    Poulos TL, Freer ST, Alden RA, Edwards SL, Skogland U, Takio K, Eriksson B, Xuong N-H, Yonetani T, Kraut J (1980) J Biol Chem 255: 575Google Scholar
  125. 123. (b)
    Finzel BC, Poulos TL, Kraut J (1984) J Biol Chem 259: 13027Google Scholar
  126. 124.
    Murthy MRN, Reid TJ, Sicignano A, Tanaka N, Rossmann MG (1981) J Mol Biol 152: 465CrossRefGoogle Scholar
  127. 125.
    Miller MA, Shaw A, Kraut J (1994) Nature Struct Biol 1: 524CrossRefGoogle Scholar
  128. 126.
    Phillips SE, Schoenborn BP (1981) Nature 292: 81CrossRefGoogle Scholar
  129. 127. (a)
    Ozaki S, Matsui T, Watanabe Y (1996) J Am Chem Soc118: 9784CrossRefGoogle Scholar
  130. 127. (b)
    Ozaki S-I, Matsui T, Watanabe Y (1997) J Am Chem Soc119: 6666CrossRefGoogle Scholar
  131. 127. (c)
    Matsui T, Ozaki S, Watanabe Y (1997) J Biol Chem 272: 32731CrossRefGoogle Scholar
  132. 128.
    Matsui T, Ozaki S, Liong E, Phillips GN, Watanabe Y (1999) J Biol Chem 273: 2838CrossRefGoogle Scholar
  133. 129.
    Ozaki S-I, Yang H-J, Matsui T, Goto Y, Watanabe Y (1999) Tetrahedron Asymmetry 10: 183CrossRefGoogle Scholar
  134. 130.
    Goto Y, Matsui T, Ozaki S-I, Watanabe Y, Fukuzumi S (1999) J Am Chem Soc p 9497Google Scholar
  135. 131.
    Hill CL, Schardt BC (1980) J Am Chem Soc102: 6374CrossRefGoogle Scholar
  136. 132.
    Groves JT, Kruper WJ, Haushalter RC (1980) J Am Chem Soc102: 6375CrossRefGoogle Scholar
  137. 133.
    Hill CL, Hollanderr FJ (1982) J Am Chem Soc104: 7318CrossRefGoogle Scholar
  138. 134.
    Camenzind MJ, Hollander FJ, Hill CL (1982) Inorg Chem 21: 4301CrossRefGoogle Scholar
  139. 135.
    Schardt BC, Hollander FJ, Hill CL (1982) J Am Chem Soc104: 3964CrossRefGoogle Scholar
  140. 136.
    Smegal JA, Schedt BC, CL H (1983) J Am Chem Soc105: 3510CrossRefGoogle Scholar
  141. 137.
    Bortoloni O, Meunier B (1983) J Chem Soc Chem Commun 1364Google Scholar
  142. 138.
    Bortolini O, Ricci M, Meunier B (1986) Nouv J Chim 10: 39Google Scholar
  143. 139. (a)
    Ayougou K, Bill E, Charnock JM, Garner CD, Mandon D, Trautwein AX, Weiss R, Winkler H (1995) Angew Chem Int Ed Eng 34: 343CrossRefGoogle Scholar
  144. 139. (b)
    Schappacher M, Weiss R (1987) Inorg Chem 26: 1189CrossRefGoogle Scholar
  145. 140.
    Groves JT, Watanabe Y, McMurry TJ (1983) J Am Chem Soc105: 4489CrossRefGoogle Scholar
  146. 141.
    Groves JT, Watanabe Y (1986) Inorg Chem 25: 4808CrossRefGoogle Scholar
  147. 142.
    Early works were reviewed by Boucher LJ, Boucher LJ (1972) Coord Chem Rev 7: 289CrossRefGoogle Scholar
  148. 143.
    Fabry TL, Simo C, Javaherian K (1986) Biochim Biophys Acta 160: 118Google Scholar
  149. 144.
    Yonetaini T, Asakura T (1969) J Biol Chem 244: 4580Google Scholar
  150. 145.
    Nick RJ, Ray GB, Fish KM, Spiro TG, Groves JT (1991) J Am Chem Soc113: 1838CrossRefGoogle Scholar
  151. 146.
    Nick RJ, Ray GB, Fish KM, Spiro TG, Groves JT (1991) J Am Chem Soc113: 1838CrossRefGoogle Scholar
  152. 147. (a)
    Modi S, Saxena AK, Behere DV, Mitra S (1990) Biochim Biophys Acta 1038: 164Google Scholar
  153. 147. (b)
    Savena A, Modi S, Behere DV, Mitra S (1990) Biochim Biophys Acta 1041: 83Google Scholar
  154. 147. (c)
    Khan KK, Mondai MS, Mitra S (1996) J Chem Soc, Dalton Trans 1059Google Scholar
  155. 147. (d)
    Khan KK, Mondai MS, Mitra S (1998) J Chem Soc Dalton Trans 533Google Scholar
  156. 148.
    Makino R, Uno T, Nishimura Y, Iizuka T, Tsuboi M, Ishimura Y (1986) J Biol Chem 261: 8376Google Scholar
  157. 149.
    Low DW, Abedin S, Yang G, Winkler JR, Gray HB (1998) Inorg Chem 37: 1841CrossRefGoogle Scholar
  158. 150. (a)
    Groves JT, Stern MK (1988) J Am Chem Soc110: 8628CrossRefGoogle Scholar
  159. 150. (b)
    Czernuszewicz RC, Su YO, Stern MK, Macor KA, Kim D, Groves JT, Spiro TG (1988) J Am Chem Soc110: 4158CrossRefGoogle Scholar
  160. 151. (a)
    De Poorter B, Meunier B (1985) J Chem Soc Perkin Trans II 1735Google Scholar
  161. 151. (b)
    De Poorter B, Ricci M, Meunier B (1985) Tetrahedron Lett 26: 4459CrossRefGoogle Scholar
  162. 151. (c)
    Robert A, Meunier B (1988) New J Chem 12: 885Google Scholar
  163. 151. (d)
    Meunier B, Guilmet E, De Carvalho M-E, Poilblanc R (1984) J Am Chem Soc 106: 6668CrossRefGoogle Scholar
  164. 151. (e)
    Guilment E, Meunier B (1984) J Mol Cat 23: 115CrossRefGoogle Scholar
  165. 151. (f)
    Bernadou J, Fabiano A-S, Robert A, Meunier B (1994) J Am Chem Soc116: 9375CrossRefGoogle Scholar
  166. 152. (a)
    Razenberg JASJ, Nolte RJM, Drenth W (1986) J Chem Soc Chem Commun 277Google Scholar
  167. 152. (b)
    van der Made AW, Nolte RJM, Drenth W (1990) Recl Trav Chim Pays-Bas 109: 537Google Scholar
  168. 153. (a)
    Collman JP, Kodadeck T, Brauman JI (1986) J Am Chem Soc108: 2588CrossRefGoogle Scholar
  169. 153. (b)
    Collman JP, Brauman JI, Meunier B, Hayashi T, Kodadeck T, Raybuck SA (1985) J Am Chem Soc 107: 2000CrossRefGoogle Scholar
  170. 153. (c)
    Collman JP, Brauman JI, Hampton PD, Tanaka H, Bohle DS, Hemnre RT (1990) J Am Chem Soc112: 7980CrossRefGoogle Scholar
  171. 154.
    Groves JT, Lee J, Maria SS (1997) J Am Chem Soc119: 6269CrossRefGoogle Scholar
  172. 155.
    Collins TJ, Gordon-Wylie SW (1989) J Am Chem Soc111: 4511CrossRefGoogle Scholar
  173. 156.
    Collins TJ, Powell RD, Slebodnick C, Uffelman ES (1990) J Am Chem Soc112: 899CrossRefGoogle Scholar
  174. 157.
    Workman JM, Powell RD, Procyk AD, Collins TJ, Bocian DF (1992) Inorg Chem 31: 1548CrossRefGoogle Scholar
  175. 158. (a)
    Groves JT, Kruper WJJ (1979) J Am Chem Soc101: 7613CrossRefGoogle Scholar
  176. 158. (b)
    Groves JT, Haushalter RC (1981) J Chem Soc Chem Commun 165Google Scholar
  177. 159.
    Fujii H, Yoshimura T, Kamada H (1997) Inorg Chem 36: 1122CrossRefGoogle Scholar
  178. 160.
    Budge JR, Gatehous BMK, Nesbit MC, West BO (1981) J Chem Soc, Chem Commun 370Google Scholar
  179. 161.
    Groves JT, Kruper WJJ, Haushalter RC, Butler WM (1982) Inorg Chem 21: 1363CrossRefGoogle Scholar
  180. 162.
    Buchler JW, Lay KL, Castle L, Ullrich V (1982) Inorg Chem 21: 842CrossRefGoogle Scholar
  181. 163.
    Yamaji M, Hama Y, Miyazaki Y, Hoshino M (1992) Inorg Chem 31: 932CrossRefGoogle Scholar
  182. 164.
    Greager SE, Murray RW (1985) Inorg Chem 24: 3824CrossRefGoogle Scholar
  183. 165. (a)
    Siddall TL, Miyaura N, Huffman JC, Kochi JK (1983) J Chem Soc Chem Commun 1185Google Scholar
  184. 165. (b)
    Samsel EG, Srinivasan K, Kochi JK (1985) J Am Chem Soc107: 7606CrossRefGoogle Scholar
  185. 166.
    Holm RH (1987) Chem Rev87: 1401CrossRefGoogle Scholar
  186. 167. (a)
    Che C-M, Lau K, Lau T-C, Poon C-K (1990) J Am Chem Soc112: 5176CrossRefGoogle Scholar
  187. 167. (b)
    Leung W-H, Che C-M (1989) J Am Chem Soc111: 8812CrossRefGoogle Scholar
  188. 167. (c)
    Che C-M, Wong K-Y, Poon C-K (1985) Inorg Chem 24: 1797CrossRefGoogle Scholar
  189. 167. (d)
    Che C-M, Lai T-F, Wong K-Y (1987) Inorg Chem 26: 2289CrossRefGoogle Scholar
  190. 167. (e)
    Che C-M, Leung W-H (1987) J Chem Soc, Chem Commun 1376Google Scholar
  191. 168. (a)
    Marmion ME, Takeuchi KJ (1988) J Am Chem Soc110: 1472CrossRefGoogle Scholar
  192. 168. (b)
    Acquaye JH, Muller JG, Takeuchi KJ (1993) Inorg Chem 32: 160CrossRefGoogle Scholar
  193. 169. (a)
    Bailey AJ, Griffith WP, White AJP, Williams DJ (1994) J Chem Soc Chem Commun 1833Google Scholar
  194. 169. (b)
    El-Hendawy AM, Griffith WP, Piggott B, Williams DJ (1988) J Chem Soc Dalton Trans: 1983Google Scholar
  195. 170.
    Masuda H, Taga T, Osaki K, Sugimoto H, Mori M, Ogoshi H (1981) J Am Chem Soc 103: 2199CrossRefGoogle Scholar
  196. 171.
    Collman JP, Barnes CE, Brothers PJ, Collins TJ, Ozawa T, Gallucci JC, Ibers JA (1984) J Am Chem Soc 106: 5151CrossRefGoogle Scholar
  197. 172.
    Leung T, James BR, Dolphin D (1983) Inorg Chim Acta 79: 180CrossRefGoogle Scholar
  198. 173.
    Groves JT, Quinn R (1984) Inorg Chem 23: 3844CrossRefGoogle Scholar
  199. 174.
    Groves JT, Quinn R (1985) J Am Chem Soc107: 5790CrossRefGoogle Scholar
  200. 175.
    James BR (1992) Catal Org React 47: 245Google Scholar
  201. 176.
    Leung W-H, Che C-M (1989) J Am Chem Soc111: 8812CrossRefGoogle Scholar
  202. 177.
    Che C-W, Chung W-C, Lai T-F (1988) Inorg Chem 27: 2801CrossRefGoogle Scholar
  203. 178.
    Dubourdeaux P, Trvarés M, Grand A, Ramasseul R, Marchon J-C (1995) Inorg Chem Acta 240: 657CrossRefGoogle Scholar
  204. 179.
    Leung W-H, Che C-H, Yeung C-H, Poon C-K (1993) Polyhedron 12: 2331CrossRefGoogle Scholar
  205. 180.
    Tokita Y, Yamaguchi K, Watanabe Y, Morishima I (1993) Inorg Chem 32: 329CrossRefGoogle Scholar
  206. 181.
    Groves JT, Ahn K-H (1987) Inorg Chem 26: 3833CrossRefGoogle Scholar
  207. 182.
    Ohtake H, Higuchi T, Hirobe M (1992) J Am Chem Soc114: 10660CrossRefGoogle Scholar
  208. 183. (a)
    Buchler JW, Rohbock K (1972) Inorg Nucl Chem Lett 8: 1073CrossRefGoogle Scholar
  209. 183. (b)
    Buchler JW, Puppe L, Rohbock K, Schneehage HH (1973) Chem Ber 106: 2710CrossRefGoogle Scholar
  210. 184.
    Johnson JF, Scheidt WR (1978) Inorg Chem 17: 1280CrossRefGoogle Scholar
  211. 185.
    Colin JBC, Cian AD, Weiss R (1983) Angew Chem Int Ed Engl 22: 247CrossRefGoogle Scholar
  212. 186.
    Diebold T, Chevrier B, Weiss R (1979) Inorg Chem 18: 1193CrossRefGoogle Scholar
  213. 187.
    Tachibana J, Imamura T, Sasaki J (1993) J Chem Soc Chem Commun 1436Google Scholar
  214. 188.
    Mentzen BF, Bonnet MC, Ledon HJ (1980) Inorg Chem 19: 2061CrossRefGoogle Scholar
  215. 189.
    Guilard R, Latour J-M, Lecomte C, Marchon J-C, Protas J, Ripoll D (1978) Inorg Chem 17: 1228CrossRefGoogle Scholar
  216. 190.
    Richard P, Poncet JL, Barbe JM, Guilard R (1982) J Chem Soc Dalton Trans 1451Google Scholar
  217. 191.
    Czarnecki K, Proniewicz LM, Fujii H, Ji D, Czernuszewicz RS, Kincaid J (1999) Inorg Chem 38: 1543CrossRefGoogle Scholar
  218. 192.
    Lemtur A, Chakravorty BK, Dhar TK, Subramanian J (1984) J Phys Chem 88: 5603CrossRefGoogle Scholar
  219. 193.
    Oliver Su Y, Czernuszewicz RS, Miller LA, Spiro TG (1988) J Am Chem Soc110: 4150CrossRefGoogle Scholar
  220. 194.
    Macor KA, Czernuszewicz RS, Spiro TG (1990) Inorg Chem 29: 1996CrossRefGoogle Scholar
  221. 195.
    Chasteen ND (1981) Biological Magnetic Resonance. In: Berliner LJ, Reuben J (eds) Plenum New York, vol 3, p53Google Scholar
  222. 196.
    Fukui K, Ohya-Nishiguchi H, Kamada H (1993) J Phys Chem 97: 11858CrossRefGoogle Scholar
  223. 197.
    Schulz CE, Song H, Lee YJ, Mondal JU, Mohanrao K, Reed CA, Ann Walker F, Scheidt WR (1994) J Am Chem Soc 116: 7196CrossRefGoogle Scholar

Copyright information

© Springer Verlag Berlin Heidelberg 2000

Authors and Affiliations

  • Yoshihito Watanabe
    • 1
  • Hiroshi Fujii
    • 1
  1. 1.Institute for Molecular ScienceOkazakiJapan

Personalised recommendations