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Biological Organometallic Chemistry of B12

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Bioorganometallic Chemistry

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 17))

Abstract

Vitamin B12, the “antipernicious anemia factor” required for human and animal metabolism, was discovered in the late 1940s. B12-derivatives are cobalt complexes of the unique and remarkably complex corrin ligand, that belongs to the class of the natural tetrapyrroles. The B12-coenzymes are the organometallic cofactors in various important enzymatic reactions and are particularly relevant in the metabolism of some archaea and (other) anaerobic microorganisms. Indeed, the microorganisms are the only natural sources of the B12-derivatives, while (with the exception of the higher plants) most living organisms depend on these cobalt-corrinoids. Vitamin B12-derivatives thus hold an important position in the life sciences and have attracted particular interest from medicine, biology, chemistry and physics.

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Abbreviations

Ado:

Adenosyl

AdoCbl:

5′-Deoxy-5′-adenosylcobalamin, adenosylcobalamin, coenzyme B12

Cbl:

Cobalamin (DMB-cobamide)

CNCbl:

Cyanocobalamin

DCE:

Dichloroethene

DD:

Diol dehydratase

DMB:

5,6-Dimethylbenzimidazole

EAL:

Ethanolamine ammonia lyase

GD:

Glycerol dehydratase

GM:

Glutamate mutase

H2OCbl:

Aquocobalamin, B12a

HOCbl:

Hydroxocobalamin

ICM:

Isobutyryl-CoA mutase

LAM:

Lysine aminomutase

MeCbl:

Methylcobalamin

MGM:

Methyleneglutarate mutase

MMCM:

Methylmalonyl-CoA mutase

NHE:

Normal hydrogen electrode

NMR:

Nuclear magnetic resonance

NOE:

Nuclear Overhauser effect

PLP:

Pyridoxal-phosphate

PCE:

Tetrachloroethene

SAM:

S-adenosylmethionine (= AdoMet)

SCE:

Saturated calomel electrode

TCE:

Trichloroethene

UV:

Ultraviolet spectrum

UV-vis:

Ultraviolet visible absorbance spectrum

References

  1. Kräutler B, Ostermann S (2003) In: Guilard R (ed) The Porphyrin Handbook, vol 11. Academic Press, San Diego, p 227

    Google Scholar 

  2. Rickes EL, Brink NG, Koniuszy FR, Wood TR, Folkers K (1948) Science 107:396

    CAS  Google Scholar 

  3. Smith EL, Parker LFJ (1948) Biochem J 43:VIII

    Google Scholar 

  4. Ellenbogen L, Cooper BA (1984) In: Machlin LJ (ed) Handbook of Vitamins, Nutritional & Clinical Aspects; Food Science and Technology. Marcel Dekker, New York, p 491

    Google Scholar 

  5. Zagalak B, Friedrich B (1979) Vitamin B12. In: Proceedings of the 3rd European Symposium on Vitamin B12and Intrinsic Factor). Walter de Gruyter, Berlin

    Google Scholar 

  6. Kräutler B, Arigoni D, Golding BT (eds) (1998) Vitamin B12and B12-Proteins. Wiley, Weinheim

    Google Scholar 

  7. Hodgkin DC, Pickworth J, Robertson JH, Trueblood KN, Prosen RJ, White JG (1955) Nature (London) 176:325

    CAS  Google Scholar 

  8. Hodgkin DC, Kamper J, Mackay M, Pickworth J, Trueblood KN, White JG (1956) Nature (London) 178:64

    CAS  Google Scholar 

  9. Lenhert PG, Hodgkin DC (1961) Nature 192:937

    CAS  Google Scholar 

  10. Eschenmoser A, Wintner CE (1977) Science 196:1410

    CAS  Google Scholar 

  11. Eschenmoser A (1982) Nova Acta Leopoldina 55:5

    Google Scholar 

  12. Woodward RB (1979) In: Friedrich W (ed) Vitamin B12, Proceedings of the 3rd European Symposium on Vitamin B12and Intrinsic Factor. Walter de Gruyter, Berlin, p 37

    Google Scholar 

  13. Battersby AR (1998) In: Kräutler B, Arigoni D, Golding BT (eds) Vitamin B12and B12-Proteins. Wiley, Weinheim, p 47

    Google Scholar 

  14. Blanche F, Cameron B, Crouzet J, Debussche L, Thibaut D, Vuilhorgne M, Leeper FJ, Battersby AR (1995) Angew Chem Int Ed Engl 34:383

    CAS  Google Scholar 

  15. Scott AI (1998) In: Kräutler B, Arigoni D, Golding BT (eds) Vitamin B12and B12-Proteins. Wiley, Weinheim, p 81

    Google Scholar 

  16. Scott AI, Roessner CA, Santander PJ (2003) In: Guilard R (ed) The Porphyrin Handbook, vol 12. Academic Press, San Diego, p 211

    Google Scholar 

  17. Drennan CL, Huang S, Drummond JT, Matthews RG, Ludwig ML (1994) Science 266:1669

    CAS  Google Scholar 

  18. Mancia F, Keep NH, Nakagawa A, Leadlay PF, McSweeney S, Rasmussen B, Diat O, Evans PR (1996) Structure 4:339

    CAS  Google Scholar 

  19. Reitzer R, Gruber K, Jogl G, Wagner UG, Bothe H, Buckel W, Kratky C (1999) Structure 7:891

    CAS  Google Scholar 

  20. Shibata N, Masuda J, Tobimatsu T, Toraya T, Suto K, Morimoto Y, Yasuoka N (1999) Structure 7:997

    CAS  Google Scholar 

  21. Sintchak MD, Arjara G, Kellogg BA, Stubbe J, Drennan CD (2002) Nature Struct Biol 9:293

    CAS  Google Scholar 

  22. Pratt JM (1972) Inorganic Chemistry of Vitamin B12. Academic Press, New York

    Google Scholar 

  23. Friedrich W (1975) In: Dirscherl W (ed) Fermente, Hormone und Vitamine, vol III/2. Georg Thieme Verlag, Stuttgart, p 173

    Google Scholar 

  24. Dolphin D (ed) (1982) B12. Wiley, New York

    Google Scholar 

  25. Banerjee R (ed) (1999) Chemistry and Biochemistry of B12. Wiley, New York

    Google Scholar 

  26. Brown KL (2005) Chem Rev 105:2075

    CAS  Google Scholar 

  27. Glusker JP (1982) In: Dolphin D (ed) B12, vol I. Wiley, New York, p 23

    Google Scholar 

  28. Kratky C, Kräutler B (1999) In: Banerjee R (ed) Chemistry and Biochemistry of B12. Wiley, New York, p 9

    Google Scholar 

  29. Kräutler B (1998) In: Kräutler B, Arigoni D, Golding BT (eds) Vitamin B12and B12-Proteins. Wiley, Weinheim, p 517

    Google Scholar 

  30. Moss GP (1987) Pure Appl Chem 6:779

    Google Scholar 

  31. Kräutler B, Konrat R, Stupperich E, Färber G, Gruber K, Kratky C (1994) Inorg Chem 33:4128

    Google Scholar 

  32. Randaccio L, Furlan M, Geremia S, Šlouf M, Srnova I, Toffoli D (2000) Inorg Chem 39:3403

    CAS  Google Scholar 

  33. Stoeckli-Evans H, Edmond E, Hodgkin DC (1972) J Chem Soc Perkin Trans 2:605

    Google Scholar 

  34. Brown KL, Evans DR, Zubkowski JD, Valente EJ (1996) Inorg Chem 35:415

    CAS  Google Scholar 

  35. Brown KL, Zou X, Wu G-Z, Zubkowski JD, Valente EJ (1995) Polyhedron 14:1621

    CAS  Google Scholar 

  36. Gruber K, Jogl G, Klintschar G, Kratky C (1998) In: Kräutler B, Arigoni D, Golding BT (eds) Vitamin B12and B12-Proteins. Wiley, Weinheim, p 335

    Google Scholar 

  37. Kräutler B, Fieber W, Ostermann S, Fasching M, Ongania K-H, Gruber K, Kratky C, Mikl C, Siebert A, Diekert G (2003) Helv Chim Acta 86:3698

    Google Scholar 

  38. Kopf J, von Deuten K, Bieganowski R, Friedrich W (1981) Z Naturforsch 36c:506

    Google Scholar 

  39. Kunze S, Zobi F, Kurz P, Spingler B, Alberto R (2004) Angew Chem Int Ed Engl 43:5025

    CAS  Google Scholar 

  40. Kratky C, Färber G, Gruber K, Wilson K, Dauter Z, Noltin H-F, Konrat R, Kräutler B (1995) J Am Chem Soc 117:4654

    CAS  Google Scholar 

  41. Randaccio L, Geremia S, Stener M, Toffoli D, Zangrando E (2002) Eur J Inorg Chem 2002(1):93

    Google Scholar 

  42. Garau G, Geremia S, Marzilli LG, Nardin G, Randaccio L, Tauzher G (2003) Acta Cryst B59:51

    Google Scholar 

  43. Perry CB, Fernandes MA, Brown KL, Zou X, Valente EJ, Marques HM (2003) Eur J Inorg Chem 2003(11):2095

    Google Scholar 

  44. Venkatesan K, Dale D, Hodgkin DC, Nockols CE, Moor FH, O'Connor BH (1971) Proc Roy Soc London Ser A 323:455

    CAS  Google Scholar 

  45. Fischli A, Daly JJ (1980) Helv Chim Acta 63:1628

    CAS  Google Scholar 

  46. Kamiya K, Kennard O (1982) J Chem Soc Perkin Trans 1:2279

    Google Scholar 

  47. Markwell AJ, Pratt JM, Shaikjee MS, Toerien JG (1987) J Chem Soc Dalton Trans 1987(6):1349

    Google Scholar 

  48. Kräutler B, Caderas C, Konrat R, Puchberger M, Kratky C (1995) Helv Chim Acta 78:81

    Google Scholar 

  49. Lewis NJ, Nussberger R, Kräutler B, Eschenmoser A (1983) Angew Chem Int Ed Engl 22:736

    Google Scholar 

  50. Nussbaumer C, Arigoni D (1983) Angew Chem Int Ed Engl 22:737

    Google Scholar 

  51. Kräutler B, Keller W, Kratky C (1989) J Am Chem Soc 111:8936

    Google Scholar 

  52. Langen P, Lehmann M, Wilkinson C, Jogl G, Kratky C (1999) Acta Cryst D55:51

    Google Scholar 

  53. Kräutler B, Keller W, Hughes M, Caderas C, Kratky C (1987) J Chem Soc Chem Comm 1987(21):1678

    Google Scholar 

  54. Lenhert PG (1968) Proc Roy Soc London A303:45

    CAS  Google Scholar 

  55. Savage HFJ, Lindley PF, Finney JL, Timms PA (1987) Acta Cryst B43:296

    Google Scholar 

  56. Bouquiere JP, Finney JL, Lehmann MS, Lindley PF, Savage HFJ (1993) Acta Cryst B49:79

    Google Scholar 

  57. Ouyang L, Rulis P, Ching WY, Nardin G, Randaccio L (2004) Inorg Chem 43:1235

    CAS  Google Scholar 

  58. Brown KL, Cheng S, Zou X, Li J, Chen G, Valente EJ, Zubkowski JD, Marques HM (1998) Biochem 37:9704

    CAS  Google Scholar 

  59. Sando GN, Blakley RL, Hogenkamp HP, Hoffmann B (1975) J Biol Chem 250:8774

    CAS  Google Scholar 

  60. Krouwer JS, Holmquist B, Kipnes RS, Babior BM (1980) Bioch Biophys Acta 612:153

    CAS  Google Scholar 

  61. Pagano TG, Marzilli GL, Flocco MM, Tsai L, Carrell HL, Glusker JP (1991) J Am Chem Soc 113:531

    CAS  Google Scholar 

  62. Gschösser S, Hannak RB, Konrat R, Gruber K, Mikl C, Kratky C, Kräutler B (2005) Chem Eur J 11:81

    Google Scholar 

  63. Gruber K, Reitzer R, Kratky C (2001) Angew Chem Int Ed Engl 40:3377

    CAS  Google Scholar 

  64. Alcock NW, Dixon RM, Golding BT (1985) J Chem Soc Chem Commun 1985(9):603

    Google Scholar 

  65. Rossi M, Glusker JP, Randaccio L, Summers MF, Toscano PJ, Marzilli LG (1985) J Am Chem Soc 107:1729

    CAS  Google Scholar 

  66. Brown KL, Cheng S, Zou X, Zubkowski JD, Valente EJ, Knapton L, Marques HM (1997) Inorg Chem 36:3666

    CAS  Google Scholar 

  67. Wagner T, Afshar CE, Carrell HL, Glusker JP (1999) Inorg Chem 38:1785

    CAS  Google Scholar 

  68. Fasching M, Schmidt W, Kräutler B, Stupperich E, Schmidt A, Kratky C (2000) Helv Chim Acta 83:2295

    CAS  Google Scholar 

  69. McCauley KM, Pratt DA, Wilson SR, Shey J, Burkey TJ, van der Donk WA (2005) J Am Chem Soc 127:1126

    CAS  Google Scholar 

  70. McCauley KM, Wilson SR, van der Donk WA (2003) J Am Chem Soc 125:4410

    CAS  Google Scholar 

  71. Purcell KF, Kotz JC (1977) Inorganic Chemistry. Holt-Saunders, Philadelphia

    Google Scholar 

  72. De Ridder DJA, Zangrando E, Bürgi H-B (1996) J Mol Struct 374:63

    Google Scholar 

  73. Pett VB, Liebman MN, Murray-Rust P, Prasad K, Glusker JP (1987) J Am Chem Soc 109:3207

    CAS  Google Scholar 

  74. Brown KL (1999) In: Banerjee R (ed) Chemistry and Biochemistry of B12. Wiley, New York, p 197

    Google Scholar 

  75. Kräutler B (1998) In: Kräutler B, Arigoni D, Golding BT (eds) Vitamin B12and B12-Proteins. Wiley, Weinheim, p 3

    Google Scholar 

  76. Fieber W, Hoffmann B, Schmidt W, Stupperich E, Konrat R, Kräutler B (2002) Helv Chim Acta 85:927

    CAS  Google Scholar 

  77. Konrat R, Tollinger M, Kräutler B (1998) In: Kräutler B, Arigoni D, Golding BT (eds) Vitamin B12and B12-Proteins. Wiley, Weinheim, p 349

    Google Scholar 

  78. Summers MF, Marzilli LG, Bax A (1986) J Am Chem Soc 108:2093

    Google Scholar 

  79. Bax A, Marzilli LG, Summers MF (1987) J Am Chem Soc 109:566

    CAS  Google Scholar 

  80. Benn R, Mynott R (1985) Angew Chem Int Ed Engl 24:333

    Google Scholar 

  81. Pagano TG, Yohannes PG, Hay BP, Scott JR, Finke RG, Marzilli LG (1989) J Am Chem Soc 111:1484

    CAS  Google Scholar 

  82. Tollinger M, Konrat R, Kräutler B (1999) Helv Chim Acta 82:1596

    CAS  Google Scholar 

  83. Kontaxis G, Riether D, Hannak RB, Tollinger M, Kräutler B (1999) Helv Chim Acta 82:848

    CAS  Google Scholar 

  84. Kräutler B, Caderas C (1984) Helv Chim Acta 67:1891

    Google Scholar 

  85. Randaccio L, Furlan M, Geremia S, Slouf M (1998) Inorg Chem 37:5390

    CAS  Google Scholar 

  86. Kräutler B (1987) Helv Chim Acta 70:1268

    Google Scholar 

  87. Kräutler B (1999) In: Banerjee R (ed) Chemistry and Biochemistry of B12. Wiley, New York, p 315

    Google Scholar 

  88. Ragsdale SW (1991) Crit Rev Biochem Mol Biol 26:261

    CAS  Google Scholar 

  89. Steiger B, Ruhe A, Walder L (1990) Anal Chem 62:759

    CAS  Google Scholar 

  90. Lexa D, Savéant J-M (1983) Acc Chem Res 16:2235

    Google Scholar 

  91. Schrauzer GN, Deutsch E, Windgassen RJ (1968) J Am Chem Soc 90:2441

    CAS  Google Scholar 

  92. Chemaly SM, Pratt JM (1984) J Chem Soc Dalton Trans 4:595

    Google Scholar 

  93. Endicott JF, Netzel TL (1979) J Am Chem Soc 101:4000

    CAS  Google Scholar 

  94. Lexa D, Savéant JM, Zickler J (1977) J Am Chem Soc 99:2786

    CAS  Google Scholar 

  95. Lexa D, Savéant JM (1976) J Am Chem Soc 98:2652

    CAS  Google Scholar 

  96. de Tacconi NR, Lexa D, Savéant JM (1979) J Am Chem Soc 101:467

    Google Scholar 

  97. Faure D, Lexa D, Savéant JM (1982) J Electroanal Chem 140:269

    CAS  Google Scholar 

  98. Faure D, Lexa D, Savéant JM (1982) J Electroanal Chem 140:285

    CAS  Google Scholar 

  99. Faure D, Lexa D, Savéant JM (1982) J Electroanal Chem 140:297

    CAS  Google Scholar 

  100. Bard AJ, Faulkner LR (1980) Electrochemical Methods. Wiley, New York

    Google Scholar 

  101. Rubinson KA, Itabashi E, Mark HB (1982) Inorg Chem 21:3571

    CAS  Google Scholar 

  102. Rubinson KA, Parekh HV, Itabashi E, Mark HB (1983) Inorg Chem 22:458

    CAS  Google Scholar 

  103. Lexa D, Savéant JM (1975) J Chem Soc Chem Commun 1975(21):872

    Google Scholar 

  104. Lexa D, Savéant JM, Zickler J (1980) J Am Chem Soc 102:2654

    CAS  Google Scholar 

  105. Lexa D, Saveant J-M, Zickler J (1980) J Am Chem Soc 102:4851

    CAS  Google Scholar 

  106. Lexa D, Savéant JM (1978) J Am Chem Soc 100:3220

    CAS  Google Scholar 

  107. Zhiu D-L, Tinembart O, Scheffold R, Walder L (1990) Helv Chim Acta 73:2225

    Google Scholar 

  108. Martin BD, Finke RG (1992) J Am Chem Soc 114:585

    CAS  Google Scholar 

  109. Waddington MD, Finke RG (1993) J Am Chem Soc 115:4629

    CAS  Google Scholar 

  110. Hannak RB (1996) Dissertation, University of Innsbruck

    Google Scholar 

  111. Kräutler B, Dérer T, Liu P, Mühlecker W, Puchberger M, Gruber K, Kratky C (1995) Angew Chem Int Ed Engl 34:84

    Google Scholar 

  112. Hannak RB, Färber G, Konrat R, Kräutler B (1997) J Am Chem Soc 119:2313

    CAS  Google Scholar 

  113. Puchberger M, Konrat R, Kräutler B (2003) Helv Chim Acta 86:1453

    CAS  Google Scholar 

  114. Tollinger M, Dérer T, Konrat R, Kräutler B (1997) J Mol Catal A116:147

    CAS  Google Scholar 

  115. Brown KL (1982) In: Dolphin D (ed) B12, vol I. Wiley, New York, p 245

    Google Scholar 

  116. Hogenkamp HPC (1982) In: Dolphin D (ed) B12, vol I. Wiley, New York, p 295

    Google Scholar 

  117. Halpern J (1982) In: Dolphin D (ed) B12, vol I. Wiley, New York, p 501

    Google Scholar 

  118. Golding BT (1982) In: Dolphin D (ed) B12, vol I. Wiley, New York, p 543

    Google Scholar 

  119. Halpern J (1985) Science 227:869

    CAS  Google Scholar 

  120. Rétey J (1982) In: Dolphin D (ed) B12, vol II. Wiley, New York, p 357

    Google Scholar 

  121. Rétey J (1998) In: Kräutler B, Arigoni D, Golding BT (eds) Vitamin B12and B12-Proteins. Wiley, Weinheim, p 273

    Google Scholar 

  122. Hay BP, Finke RG (1986) J Am Chem Soc 108:4820

    CAS  Google Scholar 

  123. Finke RG (1998) In: Kräutler B, Arigoni D, Golding BT (eds) Vitamin B12and B12-Proteins. Wiley, Weinheim, p 383

    Google Scholar 

  124. Matthews RG, Banerjee RV, Ragsdale SW (1990) BioFactors 2:147

    CAS  Google Scholar 

  125. Matthews RG (1999) In: Banerjee R (ed) Chemistry and Biochemistry of B12. Wiley, New York, p 681

    Google Scholar 

  126. Sauer K, Thauer RK (1999) In: Banerjee R (ed) Chemistry and Biochemistry of B12. Wiley, New York, p 655

    Google Scholar 

  127. Harms U, Thauer RK (1998) In: Kräutler B, Arigoni D, Golding BT (eds) Vitamin B12and B12-Proteins. Wiley, Weinheim, p 157

    Google Scholar 

  128. Brown KL, Zhou L, Zhao D, Cheng S, Zou X (1998) In: Kräutler B, Arigoni D, Golding BT (eds) Vitamin B12and B12-Proteins. Wiley, Weinheim, p 417

    Google Scholar 

  129. Pratt JM (1982) In: Dolphin D (ed) B12, vol I. Wiley, New York, p 325

    Google Scholar 

  130. Grate JG, Schrauzer GN (1979) J Am Chem Soc 101:4601

    CAS  Google Scholar 

  131. Chemaly SM, Pratt JM (1980) J Chem Soc Dalton Trans 1980(11):2259

    Google Scholar 

  132. Schrauzer GN, Deutsch E (1969) J Am Chem Soc 91:3341

    CAS  Google Scholar 

  133. Bonnett R (1982) In: Dolphin D (ed) B12, vol I. Wiley, New York, p 201

    Google Scholar 

  134. Kräutler B (1988) In: Glockling F (ed) The Biological Alkylation of Heavy Elements. Royal Society of Chemistry, London, p 168

    Google Scholar 

  135. Pailes WH, Hogenkamp HPC (1968) Biochem 7:4160

    CAS  Google Scholar 

  136. Milton P, Brown TL (1977) J Am Chem Soc 99:1390

    CAS  Google Scholar 

  137. Hogenkamp HPC, Bratt GT, Sun S (1985) Biochem 24:6428

    CAS  Google Scholar 

  138. Drennan CL, Matthews RG, Ludwig ML (1994) Curr Opin Struct Biol 4:919

    CAS  Google Scholar 

  139. Kräutler B (1995) In: Maskill H (ed) Organic Reactivity: Physical and Biological Aspects. Royal Society of Chemistry, London, p 209

    Google Scholar 

  140. Jensen MP, Halpern J (1999) J Am Chem Soc 121:2181

    CAS  Google Scholar 

  141. Mosimann H, Kräutler B (2000) Angew Chem Int Ed Engl 39:393

    CAS  Google Scholar 

  142. Galliker PK, Gräther O, Rümmler M, Fitz W, Arigoni D (1998) In: Kräutler B, Arigoni D, Golding BT (eds) Vitamin B12and B12-Proteins. Wiley, Weinheim, p 447

    Google Scholar 

  143. Cole AG, Yoder LM, Shiang JJ, Anderson NA, Walker LAI, Banaszak Holl MM, Sension RJ (2002) J Am Chem Soc 124:434

    CAS  Google Scholar 

  144. Tinembart O, Walder L, Scheffold R (1988) Ber Bunsenges Phys Chem 92:1225

    CAS  Google Scholar 

  145. Stupperich E, Konle R, Lehle M (1998) In: Kräutler B, Arigoni D, Golding BT (eds) Vitamin B12and B12-Proteins. Wiley, Weinheim, p 179

    Google Scholar 

  146. Renz P (1999) In: Banerjee R (ed) Chemistry and Biochemistry of B12. Wiley, New York, p 557

    Google Scholar 

  147. Nexø E (1998) In: Kräutler B, Arigoni D, Golding BT (eds) Vitamin B12and B12-Proteins. Wiley, Weinheim, p 461

    Google Scholar 

  148. Stupperich E, Nexø E (1991) Eur J Biochem 199:299

    CAS  Google Scholar 

  149. Eschenmoser A (1988) Angew Chem Int Ed Engl 27:5

    Google Scholar 

  150. Hoffmann B, Oberhuber M, Stupperich E, Bothe H, Buckel W, Konrat R, Kräutler B (2000) J Bacteriol 182:4773

    CAS  Google Scholar 

  151. Limbach PA, Crain PF, McCloskey JA (1994) Nucleic Acids Res 22:2183

    CAS  Google Scholar 

  152. Poppe L, Hull WE, Nitsche R, Graf T, Stupperich E, Rétey J (1999) Helv Chim Acta 82:1250

    CAS  Google Scholar 

  153. Banerjee R, Ragsdale SW (2003) Annu Rev Biochem 72:209

    CAS  Google Scholar 

  154. Matthews RG (2001) Acc Chem Res 34:681

    CAS  Google Scholar 

  155. Bandarian V, Ludwig ML, Matthews RG (2003) Proc Nat Acad Sci USA 100:8156

    CAS  Google Scholar 

  156. Ragsdale SW, Kumar M, Zhao S, Menon S, Seravalli J, Doukov T (1998) In: Kräutler B, Arigoni D, Golding BT (eds) Vitamin B12and B12-Proteins. Wiley, Weinheim, p 167

    Google Scholar 

  157. Drennan et al. (2004) J Biol Inorg Chem 9:511

    Google Scholar 

  158. Ferry JG (1995) Annu Rev Microbiol 49:305

    CAS  Google Scholar 

  159. Doukov T, Seravalli J, Stezowski JJ, Ragsdale SW (2000) Structure 8:817

    CAS  Google Scholar 

  160. Zydowsky TM, Courtney LF, Frasca V, Kobayashi K, Shimizu H, Yuen LD, Matthews RG, Benkovic SJ, Floss HG (1986) J Am Chem Soc 108:3152

    CAS  Google Scholar 

  161. Zydowsky LD, Zydowsky TM, Haas ES, Brown JW, Reeve JN, Floss HG (1987) J Am Chem Soc 109:7922

    CAS  Google Scholar 

  162. Lebertz H, Simon H, Courtney LF, Benkovic SJ, Zydowsky LD, Lee K, Floss HG (1987) J Am Chem Soc 103:3173

    Google Scholar 

  163. Ludwig ML, Evans PR (1999) In: Banerjee R (ed) Chemistry and Biochemistry of B12. Wiley, New York, p 595

    Google Scholar 

  164. Peariso K, Goulding CW, Huang S, Matthews RG, Penner-Hahn JE (1998) J Am Chem Soc 120:8410

    CAS  Google Scholar 

  165. Bandarian V, Pattridge KA, Lennon BW, Huddler DR, Matthews RG, Ludwig ML (2002) Nature Struct Biol 9:53

    CAS  Google Scholar 

  166. Drennan CL, Dixon MM, Hoover DM, Jarrett JT, Goulding CW, Matthews RG, Ludwig ML (1998) In: Kräutler B, Arigoni D, Golding BT (eds) Vitamin B12and B12-Proteins. Wiley, Weinheim, p 133

    Google Scholar 

  167. Marsh ENG, Holloway DE (1992) FEBS Lett 310:167

    CAS  Google Scholar 

  168. Evans JC, Huddler DP, Hilgers MT, Romanchuk G, Matthews RG, Ludwig ML (2004) Proc Nat Acad Sci USA 101:3729

    CAS  Google Scholar 

  169. Stupperich E, Eisinger HJ, Albrecht PJ (1990) Eur J Biochem 193:105

    CAS  Google Scholar 

  170. Kräutler B (1994) In: Schneider G (ed) Carbon Dioxide Fixation and Reduction in Biological and Model Systems: Proceedings of the Royal Swedish Academy of Sciences Nobel Symposium 1991. Oxford University Press, Oxford, p 83

    Google Scholar 

  171. Kräutler B, Kratky C (1996) Angew Chem Int Ed Engl 35:168

    Google Scholar 

  172. Jarrett JT, Amaratunga M, Drennan CL, Scholten JD, Sands RH, Ludwig ML, Matthews RG (1996) Biochem 35:2464

    CAS  Google Scholar 

  173. Marsh ENG, Drennan CL (2001) Curr Opin Struct Biol 5:499

    CAS  Google Scholar 

  174. Banerjee R, Chowdhury S (1999) In: Banerjee R (ed) Chemistry and Biochemistry of B12. Wiley, New York, p 707

    Google Scholar 

  175. Buckel W, Bröker G, Bothe H, Pierik AJ (1999) In: Banerjee R (ed) Chemistry and Biochemistry of B12. Wiley, New York, p 757

    Google Scholar 

  176. Gruber K, Kratky C (2002) Curr Opin Struct Biol 6:598

    CAS  Google Scholar 

  177. Zerbe-Burckhardt K, Ratnatilleke A, Vrijbloed JW, Robinson JA (1999) In: Banerjee R (ed) Chemistry and Biochemistry of B12. Wiley, New York, p 859

    Google Scholar 

  178. Toraya T (2003) Chem Rev 103:2095

    CAS  Google Scholar 

  179. Bandarian V, Reed GH (1999) In: Banerjee R (ed) Chemistry and Biochemistry of B12. Wiley, New York, p 811

    Google Scholar 

  180. Frey PA, Chang CH (1999) In: Banerjee R (ed) Chemistry and Biochemistry of B12. Wiley, New York, p 835

    Google Scholar 

  181. Baker JJ, Stadtman TC (1982) In: Dolphin D (ed) B12, vol II. Wiley, New York, p 203

    Google Scholar 

  182. Stubbe J, Licht S, Gerfen G, Silva D, Booker S (1998) In: Kräutler B, Arigoni D, Golding BT (eds) Vitamin B12and B12-Proteins. Wiley, Weinheim, p 321

    Google Scholar 

  183. Rétey J (1999) In: Banerjee R (ed) Chemistry and Biochemistry of B12. Wiley, New York, p 271

    Google Scholar 

  184. Rétey J (1990) Angew Chem Int Ed Engl 29:355

    Google Scholar 

  185. Bothe H, Bröker G, Müller U, Schall I, Textor S, Golding BT, Buckel W (1998) In: Kräutler B, Arigoni D, Golding BT (eds) Vitamin B12and B12-Proteins. Wiley, Weinheim, p 253

    Google Scholar 

  186. Beatrix B, Zelder O, Linder D, Buckel W (1994) Eur J Biochem 221:101

    CAS  Google Scholar 

  187. Marsh ENG (2000) Bioorg Chem 28:176

    CAS  Google Scholar 

  188. Chowdhury S, Banerjee R (2000) J Am Chem Soc 122:5417

    CAS  Google Scholar 

  189. Chowdhury S, Banerjee R (2000) Biochem 39:7998

    CAS  Google Scholar 

  190. Brooks AJ, Vlasie M, Banerjee R, Brunold TC (2004) J Am Chem Soc 126:8167

    CAS  Google Scholar 

  191. Golding BT, Anderson RJ, Ashwell S, Edwards CH, Garnett I, Kroll F, Buckel W (1998) In: Kräutler B, Arigoni D, Golding BT (eds) Vitamin B12and B12-Proteins. Wiley, Weinheim, p 201

    Google Scholar 

  192. Smith DM, Golding BT, Radom L (1999) J Am Chem Soc 121:1383

    CAS  Google Scholar 

  193. Loferer MJ, Webb BM, Grant GH, Liedl KR (2003) J Am Chem Soc 125:1072

    CAS  Google Scholar 

  194. Evans PR, Mancia F (1998) In: Kräutler B, Arigoni D, Golding BT (eds) Vitamin B12and B12-Proteins. Wiley, Weinheim, p 217

    Google Scholar 

  195. Gruber K, Kratky C (2001) In: Wieghart K (ed) Handbook of Metalloproteins. Wiley, Chichester, p 995

    Google Scholar 

  196. Mancia F, Evans PR (1998) Structure 6:711

    CAS  Google Scholar 

  197. Mancia F, Smith GA, Evans PR (1999) Biochem 38:7999

    CAS  Google Scholar 

  198. Barker HA, Weissbach H, Smyth RD (1964) J Biol Chem 239:3260

    CAS  Google Scholar 

  199. Buckel W, Golding BT (1996) Chem Rev Soc 25:329

    CAS  Google Scholar 

  200. Holloway DE, Marsh ENG (1994) J Biol Chem 269:20425

    CAS  Google Scholar 

  201. Barker HA, Weissbach H, Smith RD (1958) Proc Nat Acad Sci USA 44:1093

    CAS  Google Scholar 

  202. Marsh ENG, Ballou DP (1998) Biochem 37:11864

    CAS  Google Scholar 

  203. Cheng M-C, Marsh ENG (2004) Biochem 43:2155

    CAS  Google Scholar 

  204. Chih H-W, Marsh ENG (2000) J Am Chem Soc 122:10732

    CAS  Google Scholar 

  205. Wetmore SD, Smith DM, Golding BT, Radom L (2001) J Am Chem Soc 123:7963

    CAS  Google Scholar 

  206. Tollinger M, Konrat R, Hilbert BH, Marsh EN, Kräutler B (1998) Structure 6:1021

    CAS  Google Scholar 

  207. Hoffmann B, Tollinger M, Konrat R, Huhta M, Marsh ENG, Kräutler B (2001) ChemBioChem 2:643

    CAS  Google Scholar 

  208. Hoffmann B, Konrat R, Bothe H, Buckel W, Kräutler B (1999) Eur J Biochem 263:178

    CAS  Google Scholar 

  209. Tollinger M, Eichmüller C, Konrat R, Huhta M, Marsh ENG, Kräutler B (2001) J Mol Biol 309:777

    CAS  Google Scholar 

  210. Toraya T (1999) In: Banerjee R (ed) Chemistry and Biochemistry of B12. Wiley, New York, p 783

    Google Scholar 

  211. Tobimatsu T, Hara T, Sakaguchi M, Kishimoto Y, Wada Y, Isoda M, Sakai T, Toraya T (1995) J Biol Chem 270:7142

    CAS  Google Scholar 

  212. Tobimatsu T, Azuma M, Matsubara H, Takatori H, Niida T, Nishimoto K, Satoh H, Hayashi R, Toraya T (1996) J Biol Chem 271:22352

    CAS  Google Scholar 

  213. Yamanishi M, Yamada S, Muguruma H, Murakani Y, Tobimatsu T, Ishida A, Yamauchi J, Toraya T (1998) Biochem 124:598

    CAS  Google Scholar 

  214. Abend A, Nitsche R, Bandarian V, Stupperich E, Rétey J (1998) Angew Chem Int Ed Engl 37:625

    CAS  Google Scholar 

  215. Yamanishi M, Yunoki M, Tobimatsu T, Sato H, Matsui J, Dokiya A, Iuchi Y, Oe K, Suto K, Shibata N, Morimoto Y, Yasuoka N, Toraya T (2002) Eur J Biochem 269:4484

    CAS  Google Scholar 

  216. Toraya T, Yoshizawa K, Eda M, Yamabe T (1999) J Biochem 126:650

    CAS  Google Scholar 

  217. Masuda J, Shibata N, Morimoto Y, Toraya T, Yasuoka N (2000) Structure 8:775

    CAS  Google Scholar 

  218. Speranza G, Buckel W, Golding BT (2004) J Porphyrins Phthalocyanines 8:290

    CAS  Google Scholar 

  219. Shibata N, Masuda J, Morimoto Y, Yasuoka N, Toraya T (2002) Biochem 41:12607

    CAS  Google Scholar 

  220. Liao D-I, Dotson G, Turner I, Reiss L, Emptage M (2003) J Inorg Biochem 93:84

    CAS  Google Scholar 

  221. Kaplan BH, Stadtman ER (1968) J Biol Chem 243:1794

    CAS  Google Scholar 

  222. Abend A, Bandarian V, Nitsche R, Stupperich E, Rétey J, Reed GH (1999) Arch Biochem Biophys 370:138

    CAS  Google Scholar 

  223. Faust LRP, Connor JA, Roof DM, Hoch JA, Babior BM (1990) J Biol Chem 265:12462

    CAS  Google Scholar 

  224. Semialjac M, Schwarz H (2002) J Am Chem Soc 124:8974

    CAS  Google Scholar 

  225. Wetmore SD, Smith DM, Bennett JT, Radom L (2002) J Am Chem Soc 124:14054

    CAS  Google Scholar 

  226. Semialjac M, Schwarz H (2003) J Org Chem 68:6967

    CAS  Google Scholar 

  227. Semialjac M, Schwarz H (2004) Chem Eur J 10:2781

    CAS  Google Scholar 

  228. Tang K-H, Harms A, Frey PA (2002) Biochem 41:8767

    CAS  Google Scholar 

  229. Tang K-H, Casarez AD, Wu W, Frey PA (2003) Arch Biochem Biophys 418:49

    CAS  Google Scholar 

  230. Chang CH, Frey PA (2000) J Biol Chem 275:106

    CAS  Google Scholar 

  231. Berkovitch F, Behshad E, Tang K-H, Enns EA, Frey PA, Drennan CL (2004) Proc Nat Acad Sci USA 101:15870

    CAS  Google Scholar 

  232. Blakley RL (1982) In: Dolphin D (ed) B12, vol II. Wiley, New York, p 381

    Google Scholar 

  233. Stubbe JA, van der Donk WA (1998) Chem Rev 98:705

    CAS  Google Scholar 

  234. Stubbe J (2000) Curr Opin Struct Biol 10:731

    CAS  Google Scholar 

  235. Lawrence CC, Gerfen GJ, Samano V, Nitsche R, Robins MJ, Rétey J, Stubbe J (1999) J Biol Chem 274:7039

    CAS  Google Scholar 

  236. Sintchak MD, Arjara G, Kellogg BA, Stubbe J, Drennan CD (2002) Nature Struct Biol 9:293

    CAS  Google Scholar 

  237. Licht SS, Lawrence CC, Stubbe J (1999) Biochem 38:1234

    CAS  Google Scholar 

  238. Uhlin U, Eklund H (1994) Nature 370:533

    CAS  Google Scholar 

  239. Licht SS, Booker S, Stubbe J (1999) Biochem 38:1221

    CAS  Google Scholar 

  240. Griller D, Wayer DDM (1989) Pure & Appl Chem 61:717

    CAS  Google Scholar 

  241. Bresciani-Pahor N, Forcolin M, Marzilli LG, Randaccio L, Summers MF, Toscano PJ (1985) Coord Chem Rev 63:1

    CAS  Google Scholar 

  242. Holliger C, Wohlfahrt G, Diekert G (1999) FEMS Microbiol Rev 22:383

    Google Scholar 

  243. Ruppe S, Neumann A, Diekert G, Vetter W (2004) Environ Sci Technol 38:3063

    CAS  Google Scholar 

  244. Maillard J, Schumacher W, Vazquez F, Regeard C, Hagen WR, Holliger C (2003) Appl Environ Microbiol 69:4628

    CAS  Google Scholar 

  245. Wohlfahrt G, Diekert G (1999) In: Banerjee R (ed) Chemistry and Biochemistry of B12. Wiley, New York, p 871

    Google Scholar 

  246. Neumann A, Siebert A, Trescher T, Reinhardt S, Wohlfahrt G, Diekert G (2002) Arch Microbiol 177:420

    CAS  Google Scholar 

  247. Siebert A, Neumann A, Schubert T, Diekert G (2002) Arch Microbiol 178:443

    CAS  Google Scholar 

  248. Glod G, Angst W, Holliger C, Schwarzenbach RP (1997) Environ Sci Technol 31:253

    CAS  Google Scholar 

  249. Shey J, van der Donk WA (2000) J Am Chem Soc 122:12403

    CAS  Google Scholar 

  250. Glod G, Brodmann U, Angst W, Holliger C (1997) Environ Sci Technol 31:3154

    CAS  Google Scholar 

  251. Haglund J, Rafiq A, Ehrenberg L, Golding BT, Tørnqvist M (2000) Chem Res Toxicol 13:253

    CAS  Google Scholar 

  252. Haglund J, Magnusson A-L, Ehrenberg L, Tørnqvist M (2003) Toxicol Environ Chem 85:81

    CAS  Google Scholar 

  253. Schneider Z, Stroinski A (1987) Comprehensive B12: Chemistry, Biochemistry, Nutrition, Ecology, Medicine. Walter de Gruyter, Berlin

    Google Scholar 

  254. Alsberg T, Minten J, Haglund J, Tørnqvist M (2001) Rapid Commun Mass Spectrom 15:2438

    CAS  Google Scholar 

  255. Fred C, Haglund J, Alsberg T, Rydberg P, Minten J, Tørnqvist M (2004) J Sep Sci 27:607

    CAS  Google Scholar 

  256. Zhou DL, Walder R, Scheffold R (1992) Helv Chim Acta 75:995

    CAS  Google Scholar 

  257. Fessenden RJ, Fessenden JS (1994) Organic Chemistry. Brooks/Cole Publishing Company, Pacific Grove CA, p 320

    Google Scholar 

  258. Watson WP, Munter T, Golding BT (2004) Chem Res Toxicol 17:1562

    CAS  Google Scholar 

  259. Alpers DH, Russel-Jones GJ (1999) In: Banerjee R (ed) Chemistry and Biochemistry of B12. Wiley, New York, p 411

    Google Scholar 

  260. Rosenblatt DS, Fenton WA (1999) In: Banerjee R (ed) Chemistry and Biochemistry of B12. Wiley, New York, p 367

    Google Scholar 

  261. Hogenkamp HPC, Collins DA, Grissom CB, West FG (1999) In: Banerjee R (ed) Chemistry and Biochemistry of B12. Wiley, New York, p 385

    Google Scholar 

  262. Howard WA Jr, Bayomi A, Natarajan E, Aziza MA, El-Ahmady O, Grissom CB, West FG (1997) Bioconjugate Chem 8:498

    CAS  Google Scholar 

  263. Hogenkamp HPC, Collins DA, Live D, Benson LM, Naylor S (2000) Nucl Med Biol 27:89

    CAS  Google Scholar 

  264. Bauer JA, Morrison BH, Grane RW, Jacobs BS, Dabney S, Gamero AM, Carnevale KA, Smith DJ, Drazba J, Seetharam B, Lindner DJ (2002) J Natl Cancer Inst 94:1010

    CAS  Google Scholar 

  265. Bagnato JD, Eilers AL, Horton RA, Grissom CB (2004) J Org Chem 69:8987

    CAS  Google Scholar 

  266. Hogenkamp HPC, Collins DA (1998) In: Kräutler B, Arigoni D, Golding BT (eds) Vitamin B12 and B12-Proteins. Wiley, Weinheim, p 505

    Google Scholar 

  267. Smeltzer CC, Cannon MJ, Pinson PR, Munger JD Jr, West FG, Grissom CB (2001) Org Lett 3:799

    CAS  Google Scholar 

  268. Adamczyk M, Johnson DD, Mattingly PG, Moore JA, Pan Y (2004) Bioorg Med Chem Lett 14:3917

    CAS  Google Scholar 

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  1. Institute of Organic Chemistry & Center of Molecular Biosciences (CMBI), University of Innsbruck, 6020, Innsbruck, Austria

    Philip A. Butler & Bernhard Kräutler

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Butler, P.A., Kräutler, B. Biological Organometallic Chemistry of B12 . In: Simonneaux, G. (eds) Bioorganometallic Chemistry. Topics in Organometallic Chemistry, vol 17. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3418_004

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