The preparation of N-acetyl-Co(III)-microperoxidase-8 (NAcCoMP8) and its ligand substitution reactions: A comparison with aquacobalamin (vitamin B 12a)

Journal of Inorganic Biochemistry

Volumn 123, Issue , 2013, Pages 66-79

  Mathura, Sadhna ^a   Sannasy, Desigan ^a   De Sousa, Alvaro S ^a   Perry, Christopher B ^a   Navizet, Isabelle ^a   Marques, Helder M ^a  

^a UNIVERSITY OF THE WITWATERSRAND   (South Africa)

Author keywords

Cobalamins; DFT calculations; Ligand substitution; Microperoxidases; QTAIM calculations; Vitamin B12a

Indexed keywords

1 METHYLIMIDAZOLE; HYDROXOCOBALAMIN; HYDROXYLAMINE; LIGAND; MACROCYCLIC COMPOUND; METHOXYAMINE; N ACETYL COBALT (III) MICROPEROXIDASE 8; OCTAPEPTIDE; PORPHYRIN DERIVATIVE; PYRIDINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION KINETICS; DENSITY FUNCTIONAL THEORY; DRUG SYNTHESIS; EQUILIBRIUM CONSTANT; SUBSTITUTION REACTION; THERMODYNAMICS;

COPPER; MOLECULAR STRUCTURE; PEROXIDASES; THERMODYNAMICS; VITAMIN B 12;

EID: 84875913988     PISSN: 01620134     EISSN: 18733344     Source Type: Journal    
DOI: 10.1016/j.jinorgbio.2013.03.001     Document Type: Article

References (126)

1. C.L. Tsou Nature 164 1949 1134
2. C.L. Tsou Biochem. J. 49 1951 362 367
3. H. Tuppy, and S. Paleus Acta Chem. Scand. 9 1955 353 364
4. A. Ehrenberg, and H. Theorell Acta Chem. Scand. 9 1955 1193 1205
5. H.A. Harbury, and P.A. Loach J. Biol. Chem. 12 1960 3640 3645
6. P.A. Adams, D.A. Baldwin, and H.M. Marques R.A. Scott, A.G. Mauk, Cytochrome c: A Multidisciplinary Approach 1996 University Science Mill Valley, CA 635 692
7. H.M. Marques Dalton Trans. 2007 4371 4385
8. E.K. Yang, and K. Sauer C. Ho, Electron Transport and Oxygen Utilization 1982 Elsevier North Holland 89 94
9. O.Q. Munro, and H.M. Marques Inorg. Chem. 35 1996 3752 3767
10. J. Aron, D.A. Baldwin, H.M. Marques, J.M. Pratt, and P.A. Adams J. Inorg. Biochem. 27 1986 227 243
11. D.A. Baldwin, H.M. Marques, and J.M. Pratt J. Inorg. Biochem. 27 1986 245 254
12. M.T. Wilson, R.J. Ranson, P. Masiakowski, E. Czarnecka, and M. Brunori Eur. J. Biochem. 77 1977 193 199
13. T. Shimizu, T. Nozawa, and M. Hatano J. Biochem. (Tokyo) 91 1982 1951 1958
14. H.M. Marques, D.A. Baldwin, and J.M. Pratt J. Inorg. Biochem. 29 1987 77 91
15. A.B.M. Sadeque, T. Shimizu, and M. Hatano Inorg. Chim. Acta 135 1987 109 113
16. J.W. Owens, C.J. O'Connor, and R.J. Kassner Inorg. Chim. Acta 151 1988 107 116
17. M.M.M. Saleem, and M.T. Wilson Inorg. Chim. Acta 153 1988 99 104
18. M. Byfield, and J. Pratt J. Chem. Soc. Chem. Commun. 1992 214 215
19. H.M. Marques, M.P. Byfield, and J.M. Pratt J. Chem. Soc., Dalton Trans. 1993 1633 1639
20. C.B. Perry, T. Chick, A. Ntlokwana, G. Davies, and H.M. Marques J. Chem. Soc., Dalton Trans. 2002 449 457
21. P.R. Vashi, and H.M. Marques J. Inorg. Biochem. 98 2004 1471 1482
22. J.E. Kim, M.A. Pribisko, H.B. Gray, and J.R. Winkler Inorg. Chem. 43 2004 7953 7960
23. J.-G. Ma, J.M. Vanderkooi, J. Zhang, S.-L. Jia, and J.A. Shelnutt Biochemistry 38 1999 2787 2795
24. D.W. Low, S. Abedin, G. Yang, J.R. Winkler, and H.B. Gray Inorg. Chem. 37 1998 1841 1843
25. J.-L. Primus, M.G. Boersma, D. Mandon, S. Boeren, C. Veeger, R. Weiss, and I.M.C.M. Rietjens J. Biol. Inorg. Chem. 4 1999 274 283
26. T.P. Henning, T.G. Spring, in: WIPO (Ed.), USA, 1996.
27. T.P. Henning, T.G. Spring, Proc. Proceedings - Electrochemical Society: 99-5 (New Directions in, Electroanalytical Chemistry II)1999144-151.
28. J.L. Primus, S. Grunenwald, P.-L. Hagedoorn, A.-M. Albrecht-Gary, D. Mandon, and C. Veeger J. Am. Chem. Soc. 124 2002 1214 1221
29. M. Kobayashi, and S. Shimizu Eur. J. Biochem. 261 1999 1 9
30. 12 1999 Wiley New York
31. K.L. Brown Chem. Rev. 105 2005 2075 2149
32. B. Kräutler Biochem. Soc. Trans. 33 2005 806 810
33. J.R. Roth, J.G. Lawrence, and T.A. Bobik Annu. Rev. Microbiol. 50 1996 137 181
34. L. Knapton, and H.M. Marques Dalton Trans. 2005 889 895
35. E.A. Betterton, Ph.D. Thesis, University of the Witwatersrand, Johannesburg, 1982.
36. K.R. Ashley, M. Berggren, and M. Cheng J. Am. Chem. Soc. 97 1975 1422 1426
37. W.G. Jackson, S.S. Jurisson, and B.C. McGregor Inorg. Chem. 24 1985 1788 1790
38. C.K. Poon Coord. Chem. Rev. 10 1973 1 35
39. K.L. Brown, S. Cheng, X. Zou, J.D. Zubkowski, E.J. Valente, L. Knapton, and H.M. Marques Inorg. Chem. 36 1997 3666 3675
40. C.B. Perry, M.A. Fernandes, K.L. Brown, X. Zou, E.J. Valente, and H.M. Marques Eur. J. Inorg. Chem. 2003 2095 2107
41. H.M. Marques, J.H. Marsh, J.R. Mellor, and O.Q. Munro Inorg. Chim. Acta 170 1990 259 269
42. 12 1999 John Wiley & Sons, Inc. New York 73 112
43. H.M. Marques, L. Knapton, X. Zou, and K.L. Brown J. Chem. Soc., Dalton Trans. 2002 3195 3200
44. L. Knapton, and H.M. Marques S. Afr. J. Chem. 59 2006 43 47
45. M. Hamza J. Chem. Soc., Dalton Trans. 2002 2831 2836
46. D. Zheng, and R.L. Birke J. Am. Chem. Soc. 124 2002 9066 9067
47. M. Wolak, G. Stochel, M. Hamza, and R. Van Eldik Inorg. Chem. 39 2000 2018 2019
48. H.M. Marques, O.Q. Munro, T. Munro, M. de Wet, and P.R. Vashi Inorg. Chem. 38 1999 2312 2319
49. H.M. Marques, I. Cukrowski, and P.R. Vashi J. Chem. Soc., Dalton Trans. 2000 1335 1342
50. W.W. Reenstra, and W.P. Jencks J. Am. Chem. Soc. 101 1979 5780 5791
51. H.M. Marques, K.L. Brown, and D.W. Jacobsen J. Biol. Chem. 263 1988 12378 12383
52. W.C. Randall, and R.A. Alberty Biochemistry 5 1966 3189 3193
53. W.C. Randall, and R.A. Alberty Biochemistry 6 1967 1520 1525
54. D. Thusius J. Am. Chem. Soc. 93 1971 2629 2635
55. D. Thusius J. Chem. Soc. Chem. Commun. 1968 1183
56. H.M. Marques J. Chem. Soc., Dalton Trans. 1991 339 341
57. H.M. Marques J. Chem. Soc., Dalton Trans. 1991 1437 1442
58. G. Stochel, and R. van Eldik Inorg. Chem. 29 1990 2075 2077
59. H.M. Marques, J.C. Bradley, and L.A. Campbell J. Chem. Soc., Dalton Trans. 1992 2019 2027
60. H.M. Marques, O.Q. Munro, B.M. Cumming, and C. de Nysschen J. Chem. Soc., Dalton Trans. 1994 297
61. S. Mathura, PhD Thesis, University of the Witwatersrand, Johannesburg, 2013.
62. H.M. Marques, O.Q. Munro, and M.L. Crawcour Inorg. Chim. Acta 196 1992 221 229
63. M.J.T. Frisch, G. W. Schlegel, H. B. Scuseria, G. E. Robb, M. A. Cheeseman, J. R. Scalmani, G. Barone, V. Mennucci, B. Petersson, G. A. Nakatsuji, H. Caricato, M. Li, X. Hratchian, H. P. Izmaylov, A. F. Bloino, J. Zheng, G. Sonnenberg, J. L. Hada, M. Ehara, M. Toyota, K. Fukuda, R. Hasegawa, J. Ishida, M. Nakajima, T. Honda, Y. Kitao, O. Nakai, H. Vreven, T. Montgomery, J., J. A. Peralta, J. E. Ogliaro, F. Bearpark, M. Heyd, J. J. Brothers, E. Kudin, K. N. Staroverov, V. N. Kobayashi, R. Normand, J. Raghavachari, K. Rendell, A. Burant, J. C. Iyengar, S. S. Tomasi, J. Cossi, M. Rega, N. Millam, N. J. Klene, M. Knox, J. E. Cross, J. B. Bakken, V. Adamo, C. Jaramillo, J. Gomperts, R. Stratmann, R. E. Yazyev, O. Austin, A. J. Cammi, R. Pomelli, C. Ochterski, J. W. Martin, R. L. Morokuma, K. Zakrzewski, V. G. Voth, G. A. Salvador, P. Dannenberg, J. J. Dapprich, S. Daniels, A. D. Farkas, Ö. Foresman, J. B. Ortiz, J. V. Cioslowski, J. Fox, D. J., Gaussian, Inc., Wallingford C, 2009.
64. L. Hannibal, S.D. Bunge, R. van Eldik, D.W. Jacobsen, C. Kratky, K. Gruber, and N.E. Brasch Inorg. Chem. 46 2007 3613 3618
65. Y. Zhao, and D.G. Truhlar J. Chem. Phys. 125 2006 194101
66. A. Schaefer, H. Horn, and R. Ahlrichs J. Chem. Phys. 97 1992 2571 2577
67. K. Eichkorn, O. Treutler, H. Öhm, M. Häser, and R. Ahlrichs Chem. Phys. Lett. 240 1995 283 290
68. K. Eichkorn, F. Weigend, O. Treutler, and R. Ahlrichs Theor. Chem. Acc. 97 1997 119
69. B.I. Dunlap J. Chem. Phys. 78 1983 3140 3142
70. B.I. Dunlap J. Mol. Struct. (THEOCHEM) 529 2000 37 40
71. T.A. Keith http://aim.tkgristmill.com 2011 (Overland Park, KS)
72. J.I. Toohey Proc. Natl. Acad. Sci. U. S. A. 54 1965 934 942
73. A.D. Carraway, M.G. McCollum, and J. Peterson Inorg. Chem. 35 1996 6885 6891
74. S. Othman, A. Le Lirzin, and A. Desbois Biochemistry 32 1993 9781 9791
75. D.W. Urry, and J.W. Pettegrew J. Am. Chem. Soc. 89 1967 5276 5283
76. D.W. Urry J. Am. Chem. Soc. 89 1967 4190 4196
77. A.D. Carraway, R.S. Burkhalter, R. Timkovich, and J. Peterson J. Inorg. Biochem. 52 1993 201 207
78. A. Carraway, S. Povlock, M. Houston, D. Johnston, and J. Peterson J. Inorg. Biochem. 60 1995 267 276
79. J.S. Wang, A.L. Tsai, J. Heldt, G. Palmer, and H.E. Van Wart J. Biol. Chem. 267 1992 15310 15318
80. J.S. Wang, and H.E. Van Wart J. Phys. Chem. 93 1989 7925 7931
81. S.A. Kazmi, M.A. Mills, Z.W. Pitluk, and R.A. Scott J. Inorg. Biochem. 24 1985 9 12
82. D.C. Blumenthal, and R.J. Kassner J. Biol. Chem. 255 1980 5859 5863
83. R. Santucci, H. Reinhard, and M. Brunori J. Am. Chem. Soc. 110 1988 8536
84. V.J. Razumas, A.V. Gundavičius, J.D. Kazlauskaite, and J.J. Kulys J. Electroanal. Chem. 271 1989 155
85. H.M. Marques, and C.B. Perry J. Inorg. Biochem. 75 1999 281 291
86. L.R. Milgrom The Colours of Life: An introduction to the chemistry of porphyrins and related compounds 1997 Oxford University Press Oxford
87. R.D. Shannon Acta Crystallogr. A32 1976 751 767
88. M. Gouterman J. Chem. Phys. 30 1959 1139 1161
89. I. Navizet, C.B. Perry, P.P. Govender, and H.M. Marques J. Phys. Chem. B 116 2012 8836 8846
90. M.W. Makinen, and A.K. Churg A.B.P. Lever, H.B. Gray, Iron Porphyrins, Part 1 1983 Addison-Wesley Reading, MA 141 235
91. CCDC, Cambridge, UK, 2011.
92. 12 vol. 1 1982 Wiley-Interscience New York 23 107
93. K.L. Brown, X. Zou, and H.M. Marques J. Mol. Struct. (THEOCHEM) 453 1998 209 224
94. G. Garau, S. Geremia, L.G. Marzilli, G. Nardin, L. Randaccio, and G. Tauzher Acta Crystallogr. B 2003 51 59
95. J. Li, B.C. Noll, A.G. Oliver, G. Ferraudi, A.G. Lappin, and W.R. Scheidt Inorg. Chem. 49 2010 2398
96. H. Bang, J.O. Edwards, J. Kim, R.G. Lawler, K. Reynolds, W.J. Ryan, and D.A. Sweigart J. Am. Chem. Soc. 114 1992 2843
97. J.W. Lauher, and J.A. Ibers J. Am. Chem. Soc. 96 1974 4447
98. L. Liu, and Q.-X. Guo Chem. Rev. 101 2001 673 695
99. G.C. Hayward, H.A.O. Hill, J.M. Pratt, N.J. Vanston, and R.J.P. Williams J. Chem. Soc. A 1965 6485 6493
100. N.R. de Tacconi, D. Lexa, and J.M. Saveant J. Am. Chem. Soc. 101 1979 467
101. A.E. Martell, R.M. Smith, R.J. Motekaites, NIST, Gaithersburg, MD, 2004.
102. L. Di Costanzo, S. Geremia, L. Randaccio, F. Nastri, O. Maglio, A. Lombardi, and V. Pavone J. Biol. Inorg. Chem. 9 2004 1017 1027
103. B. Kräutler, R. Konrat, E. Stupperich, G. Färber, K. Gruber, and C. Kratky Inorg. Chem. 33 1994 4128 4139
104. P.R. Varadwaj, I. Cukrowski, and H.M. Marques J. Phys. Chem. A 112 2008 10657 10666
105. P.R. Varadwaj, and H.M. Marques Phys. Chem. Chem. Phys. 12 2010 2126 2138
106. P.R. Varadwaj, and H.M. Marques Theor. Chem. Acc. 127 2010 711 725
107. P.R. Varadwaj, A. Varadwaj, and H.M. Marques J. Phys. Chem. A 115 2011 5592 5601
108. P.R. Varadwaj, A. Varadwaj, G.H. Peslherbe, and H.M. Marques J. Phys. Chem. A 115 2011 13180 13190
109. P.R. Varadwaj, I. Cukrowski, C.B. Perry, and H.M. Marques J. Phys. Chem. A 115 2011 6629 6640
110. S.T. Howard, and T.M. Krygowski Can. J. Chem. 75 1997 1174 1181
111. S.E. O'Brien, and P.L. Popelier Can. J. Chem. 77 1999 28 36
112. R.F.W. Bader, and C.F. Matta J. Phys. Chem. A 108 2004 8385 8394
113. I. Vidal, S. Melchor, I. Alkorta, J. Elguero, M.R. Sundberg, and J.A. Dobado Organometallics 25 2006 5638 5647
114. L. González, O. Mó, M. Yáñez, and J. Elguero J. Mol. Struct. 371 1996 1 10
115. E. Espinosa, M. Souhassou, H. Lachekar, and C. Lecomte Acta Crystallogr. B 55 1999 563 572
116. S.J. Grabowski J. Phys. Chem. A 105 2000 5551 5557
117. L. Sobczyk, S.J. Grabowski, and T.M. Krygowski Chem. Rev. 105 2005 3513 3560
118. R.F.W. Bader, and H. Essén J. Chem. Phys. 80 1984 1943 1960
119. M.F. Bobrov, G.V. Popova, and V.G. Tsirelson Russ. J. Phys. Chem. 80 2006 584 590
120. E. Espinosa, I. Alkorta, J. Elguero, and E. Molins J. Chem. Phys. 117 2002 5529 5542
121. R.F.W. Bader, and C.F. Matta Inorg. Chem. 40 2001 5603 5611
122. R.F. Bader Atoms in Molecules: A Quantum Theory 1990 Oxford University Press Oxford
123. S.M. Chemaly, M. Florczak, H. Dirr, and H.M. Marques Inorg. Chem. 50 2011 8719 8727
124. R.F. Pasternack, and M.A. Cobb J. Inorg. Nucl. Chem. 35 1973 4327 4339
125. R.F. Pasternack, M.A. Cobb, and N. Sutin Inorg. Chem. 14 1975 866 873
126. E.B. Fleischer, S. Jacobs, and L. Mestichelli J. Am. Chem. Soc. 90 1967 2527 2531