Synthesis and characterization of isolable thiolatocobalamin complexes relevant to coenzyme B12-dependent ribonucleoside triphosphate reductase

Journal of Inorganic Biochemistry

Volumn 76, Issue 3-4, 1999, Pages 197-209

  Brasch, Nicola E ^a   Hsu, Tsui Ling Carolyn ^a   Doll, Kenneth M ^a   Finke, Richard G ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

Coenzyme B12; Ribonucleoside triphosphate reductase; Thiolatocobalamin complexes

Indexed keywords

COBAMAMIDE; CYANOCOBALAMIN; CYCLOHEXYLTHIOCOBALAMIN; CYSTEINYLCOBALAMIN; DRUG DERIVATIVE; GLUTATHIONE; GLUTATHIONYLCOBALAMIN; LIGAND; METHANOL; RIBONUCLEOTIDE REDUCTASE; WATER;

ARTICLE; METABOLISM; SPECTROPHOTOMETRY; SYNTHESIS;

COBAMIDES; GLUTATHIONE; LIGANDS; METHANOL; RIBONUCLEOTIDE REDUCTASES; SPECTROPHOTOMETRY; VITAMIN B 12; WATER;

EID: 0033618919     PISSN: 01620134     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0162-0134(99)00128-2     Document Type: Article

References (89)

1. J. Stubbe, Adv. Enzymol. Relat. Areas Mol. Biol. 63 (1990) 349.
2. J. Stubbe, J. Biol. Chem. 265 (1990) 5329.
3. J. Stubbe, Annu. Rev. Biochem. 58 (1989) 257.
4. J. Stubbe, J. Mol. Cell Biochem. 50 (1983) 25.
5. 12, vol. II, Wiley-Interscience, New York, 1982, Ch. 14, pp. 381-418.
6. W.H. Orme-Johnsom, H. Beinert, R.L. Blakley, J. Biol. Chem. 249 (1974) 2338.
7. G.J. Gerfen, S. Licht, J.-P. Willems, B.M. Hoffman, J. Stubbe, J. Am. Chem. Soc. 118 (1996) 8192.
8. S. Licht, G.J. Gerfen, J. Stubbe, Science 271 (1996) 477.
9. Y. Tamao, R.L. Blakley, Biochemistry 12 (1973) 24.
10. S. Booker, S. Licht, J. Broderick, J. Stubbe, Biochemistry 33 (1994) 12676.
11. S.S. Licht, S. Booker, J. Stubbe, Biochemistry 38 (1999) 1221.
12. S.S. Licht, C.C. Lawrence, J. Stubbe, Biochemistry 38 (1999) 1234.
13. S.M. Poison, L. Hansen, L.G. Marzilli, Inorg. Chem. 36 (1997) 307.
14. G.N. Schrauzer, Acc. Chem. Res. 1 (1968) 97.
15. G.N. Schrauzer, R.J. Windgassen, J. Am. Chem. Soc. 89 (1967) 3607.
16. H. Hennig, K. Ritter, J. Prakt. Chem. 337 (1995) 125.
17. Alkyl(thiolato)cobaloximes: K.L. Brown, R.G. Kallen, J. Am. Chem. Soc. 94 (1972) 1894.
18. V. Alexander, Inorg. Chim. Acta 163 (1989) 143.
19. G. Pellizer, G.R. Tauszik, G. Costa, J. Chem. Soc., Dalton Trans. (1973) 317.
20. For Co(III)Salen-thioether complexes see: K. Horiuchi, M. Mikuriya, H. Okawa, S. Kida, Bull. Chem. Soc. Jpn. 60 (1987) 3575.
21. For Co(II)Salen-thioether see: K. Horiuchi, M. Koikawa, S. Baba, H. Okawa, Y. Maeda, H. Oshio, S. Kida, Inorg. Chim. Acta 144 (1988) 99.
22. K. Nakamoto, H. Oshio, H. Okawa, W. Kanda, K. Horiuchi, S. Kida, Inorg. Chim. Acta 108 (1985) 231.
23. H. Aoi, S. Yoshikawa, Bull. Chem. Soc. Jpn. 48 (1975) 1049.
24. M. Tada, K. Sugano, T. Yoshihara, Bull. Chem. Soc. Jpn. 68 (1995) 2969.
25. M. Kijima, K. Miyamori, T. Sato, J. Org. Chem. 53 (1988) 4147.
26. J. Deniau, K.N.V. Duong, A. Gaudemer, P. Bougeard, M.D. Johnson, J. Chem. Soc., Perkin Trans. II (1981) 393.
27. N. Adler, T. Medwick, T.J. Poznanski, J. Am. Chem. Soc. 88 (1966) 5018.
28. D. Dolphin, A.W. Johnson, J. Chem. Soc. (1965) 2174.
29. D.W. Jacobsen, L.S. Troxell, K.L. Brown, Biochemistry 23 (1984) 2017.
30. G.N. Schrauzer, J.W. Sibert, Arch. Biochem. Biophys. 130 (1969) 257.
31. J.L. Peel, Biochem. J. 88 (1963) 296.
32. M. Kijima, K. Miyamori, S. Takeo, J. Org. Chem. 53 (1988) 4147.
33. S. Chowdhury, P.M. Samuel, I. Das, S. Roy, J. Chem. Soc., Chem. Commun. (1994) 1993.
34. F. Nome, J.H. Fendler, J. Chem. Soc., Dalton Trans. (1976) 1212.
35. H.A.O. Hill, J.M. Pratt, R.G. Throp, B. Ward, R.J.P. Williams, Biochem. J. 120 (1970) 263.
36. R.A. Firth, H.A.O. Hill, J.M. Pratt, R.G. Throp, R.J.P. Williams, J. Chem. Soc. A (1969) 381.
37. H.A.O. Hill, J.M. Pratt, R.J.P. Williams, J. Theor. Biol. 3 (1962) 423.
38. J.M. Pratt, J. Chem. Soc. (1964) 5154.
39. D. Cavallini, R. Scandurra, E. Barboni, M. Marcucci, FEBS Lett. 1 (1968) 272.
40. J.I. Toohey, J. Inorg. Biochem. 49 (1993) 189.
41. J.M. Pratt, R.G. Thorp, J. Chem. Soc. A (1966) 187.
42. W.C. Randall, R.A. Alberty, Biochemistry 5 (1966) 3189.
43. 12 and Intrinsic Factor, Walter de Gruyter, New York, 1979, pp. 605-608.
44. K.L. Brown, X. Zou, Abstr., 211th National Meeting of the American Chemical Society, American Chemical Society, Washington, DC, 1996, INORG489.
45. T.-L.C. Hsu, N.E. Brasch, R.G. Finke, Inorg. Chem. 37 (1998) 5109.
46. J.W. Dubnoff, Biochem. Biophys. Res. Commun. 16 (1964) 484.
47. P.Y. Law, J.M. Wood, J. Am. Chem. Soc. 95 (1973) 914.
48. K.L. Brown, X. Zou, S.R. Savon, D.W. Jacobsen, Biochemistry 32 (1993) 8421.
49. E. Pezacka, R. Green, D.W. Jacobsen, Biochem. Biophys. Res. Commun. 169 (1990) 443.
50. E.M. Scheuring, I. Sagi, M.R. Chance, Biochemistry 33 (1994) 6310.
51. T.-L.C. Hsu, K.M. Doll, R.G. Finke, experiments in progress.
52. RTPR studies: D.J. Silva, J. Stubbe, V. Samano, M.J. Robins, Biochemistry 37 (1998) 5528.
53. L. Poppe, J. Retey, Eur. J. Biochem. 245 (1997) 398.
54. T. Toraya, Y. Sugimoto, Y. Tamao, S. Shimizu, Biochemistry 10 (1971) 3475.
55. H.A. Lee Jr, R.H. Abeles, J. Biol. Chem. 238 (1963) 2367.
56. B.M. Babior, T.K. Li, Biochemistry 8 (1969) 154.
57. B.H. Kaplan, E.R. Stadtman, J. Biol. Chem. 243 (1968) 1794.
58. R.T. Taylor, M.L. Hanna, Arch. Biochem. Biophys. 141 (1970) 247.
59. R.T. Taylor, Arch. Biochem. Biophys 137 (1970) 529.
60. Related studies of RDPR: W.A. van der Donk, G. Yu, L. Pérez, R.L. Sanchez, J. Stubbe, Biochemistry 37 (1998) 6419.
61. C.C. Lawrence, G.J. Gerfen, V. Samano, R. Nitsche, J. Rétey, M.J. Robins, J. Stubbe, J. Biol. Chem. 274 (1999) 7039.
62. D.D. Tanner, N. Wada, B.C. Brownlee, Can. J. Chem. 51 (1973) 1870.
63. H.-U. Blaser, J. Halpern, J. Am. Chem. Soc. 102 (1980) 1684.
64. L. Randaccio, M. Furlan, S. Geremia, M. Soluf, Inorg. Chem. 37 (1998) 5390.
65. H.A. Barker, R.D. Smyth, H. Weissbach, J.I. Toohey, J.N. Ladd, B.E. Volcani, J. Biol. Chem. 235 (1960) 480.
66. N.E. Brasch, R.G. Finke, J. Inorg. Biochem. 73 (1999) 215.
67. L.G. Marzilli, W.O. Parker Jr., R.K. Kohli, H.L. Carell, J.P. Glusker, Inorg. Chem. 25 (1986) 127.
68. + group.
69. W.P. Jencks, K. Salvesen, J. Am. Chem. Soc. 93 (1971) 4433.
70. K.L. Brown, J.M. Hakimi, Inorg. Chim. Acta 67 (1982) L29.
71. K.L. Brown, J.M. Hakimi, D.M. Muss, Y.D. Montejano, D.W. Jacobsen, Inorg. Chem. 23 (1984) 1463.
72. G.C. Hayward, H.A.O. Hill, J.M. Pratt, N.J. Vanston, R.J.P.Williams, J. Chem. Soc. (1965) 6485.
73. H.M. Marques, K.L. Brown, D.W. Jacobsen, J. Biol. Chem. 263 (1988) 12378.
74. W.W. Reenstra, W.P. Jencks, J. Am. Chem. Soc. 101 (1979) 5780.
75. H.M. Marques, E.L.J. Breet, F.F. Prinsloo, J. Chem. Soc. (1991) 2941.
76. K.L. Brown, J.M. Hakimi, J. Am. Chem. Soc. 108 (1986) 496.
77. R. Zhao, J. Lind, G. Merényi, T. Eriksen, J. Am. Chem. Soc. 116 (1994) 12010.
78. R. Zhao, J. Lind, G. Merényi, T. Eriksen, J. Chem. Soc., Perkin Trans. II (1997) 569.
79. C.D. Garr, R.G. Finke, Inorg. Chem. 32 (1993) 4414, also Ref. [12] therein.
80. J.T. Jarrett, C.L. Drennan, M. Amaratunga, J.D. Scholten, M.L. Ludwig, R.G. Matthews, Bioorg. Med. Chem. 4 (1996) 1237.
81. R.K. Suto, N.E. Brasch, O.P. Anderson, R.G. Finke, Synthesis, characterization, and X-ray crystal structure of γ-glutamylcysteinylcobalamin, a thiolatocobalamin analog of glutathionylcobalamin, Biochemistry, in preparation.
82. B.P. Hay, R.G. Finke, Polyhedron 7 (1988) 1469.
83. D.F. Shriver, M.A. Drezdzon, The Manipulation of Air-Sensitive Compounds, Wiley, New York, 1986.
84. A.F. Boyne, G.L. Ellman, Anal. Biochem. 46 (1972) 639.
85. G.L. Ellman, Arch. Biochem. Biophys. 82 (1959) 70.
86. 12, Walter de Gruyter, Berlin, New York, 1987.
87. 12 und verwandte Corrinoide, Georg Thieme Verlag, Stuttgart, 1975, pp. 47-55, see p. 53.
88. B.P. Hay, R.G. Finke, J. Am. Chem. Soc. 108 (1986) 4820.
89. P.E. Fleming, B.E. Daikh, R.G. Finke, J. Inorg. Biochem. 69 (1998) 45.