Similarities and differences between cobalamins and cobaloximes. Accurate structural determination of methylcobalamin and of LiCl- and KCl-containing cyanocobalamins by synchrotron radiation

Inorganic Chemistry

Volumn 39, Issue 15, 2000, Pages 3403-3413

  Randaccio, Lucio ^a   Furlan, Michela ^a   Geremia, Silvano ^a   Šlouf, Miroslav ^b   Srnova, Ivana ^b   Toffoli, Daniele ^a  

^a UNIVERSITY OF TRIESTE   (Italy)

^b CHARLES UNIVERSITY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

COBALAMIN DERIVATIVE; COBALOXIME DERIVATIVE; CYANOCOBALAMIN; LITHIUM CHLORIDE; MECOBALAMIN; POTASSIUM CHLORIDE; UNCLASSIFIED DRUG;

ACCURACY; ARTICLE; CRYSTAL; CRYSTAL STRUCTURE; CRYSTALLIZATION; DRUG CONFORMATION; DRUG DETERMINATION; DRUG STRUCTURE; ELECTROCHEMISTRY; RADIATION; SPECTROSCOPY; STRUCTURE ANALYSIS; SYNCHROTRON;

EID: 0034709867     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic0001199     Document Type: Article

References (59)

1. Hodgkin, D. C.; Lindsey, J.; Sparks, R. A.; Trueblood, K. N.; White, J. G. Proc. R. Soc. 1962, A266, 494. Brink-Shomaker, C.; Cruickshank, D. W. J., Hodgkin, D. C.; Kamper, M. J.; Pilling, D. Proc. R. Soc. 1964, A278, 1 and references therein.
2. Hodgkin, D. C.; Lindsey, J.; Sparks, R. A.; Trueblood, K. N.; White, J. G. Proc. R. Soc. 1962, A266, 494. Brink-Shomaker, C.; Cruickshank, D. W. J., Hodgkin, D. C.; Kamper, M. J.; Pilling, D. Proc. R. Soc. 1964, A278, 1 and references therein.
3. Lenhert, P. G. Proc. R. Soc. 1968, 303, 45.
4. 12 Dolphin, D., Ed.; Wiley: New York, 1982; Vol. 1, p 23.
5. Rossi, M.; Glusker, J. P.; Randaccio, L.; Summers, M. F.; Toscano, P. J.; Marzilli, L. G. J. Am. Chem. Soc. 1985, 107, 1729.
6. Bresciani-Pahor, N.; Forcolin, M.; Marzilli, Randaccio, L.; Summers, M. F.; Toscano, J. P. Coord. Chem. Rev. 1985, 63, 1. Randaccio, L.; Bresciani-Pahor, N.; Zangrando, E.; Marzilli, L. G. Chem. Soc. Rev. 1989, 18, 225. Randaccio, L. Comments Inorg. Chem. 1999, 21, 327.
7. Bresciani-Pahor, N.; Forcolin, M.; Marzilli, Randaccio, L.; Summers, M. F.; Toscano, J. P. Coord. Chem. Rev. 1985, 63, 1. Randaccio, L.; Bresciani-Pahor, N.; Zangrando, E.; Marzilli, L. G. Chem. Soc. Rev. 1989, 18, 225. Randaccio, L. Comments Inorg. Chem. 1999, 21, 327.
8. Bresciani-Pahor, N.; Forcolin, M.; Marzilli, Randaccio, L.; Summers, M. F.; Toscano, J. P. Coord. Chem. Rev. 1985, 63, 1. Randaccio, L.; Bresciani-Pahor, N.; Zangrando, E.; Marzilli, L. G. Chem. Soc. Rev. 1989, 18, 225. Randaccio, L. Comments Inorg. Chem. 1999, 21, 327.
9. 12: Banerjee, R., Ed.; J. Wiley & Sons: New York, 1999. Pratt, J. M. In Metal Ions in Biological Systems; Sigel, H., Sigel, A., Eds.; Marcel Dekker Inc.: New York, 1993; Vol. 29, p 229. Marzilli, L. In Bioinorganic Catalysis; Reedijk, J., Bouwman, E., Eds.; Marcel Dekker: New York, 1999; p 423.
10. 12: Banerjee, R., Ed.; J. Wiley & Sons: New York, 1999. Pratt, J. M. In Metal Ions in Biological Systems; Sigel, H., Sigel, A., Eds.; Marcel Dekker Inc.: New York, 1993; Vol. 29, p 229. Marzilli, L. In Bioinorganic Catalysis; Reedijk, J., Bouwman, E., Eds.; Marcel Dekker: New York, 1999; p 423.
11. 12: Banerjee, R., Ed.; J. Wiley & Sons: New York, 1999. Pratt, J. M. In Metal Ions in Biological Systems; Sigel, H., Sigel, A., Eds.; Marcel Dekker Inc.: New York, 1993; Vol. 29, p 229. Marzilli, L. In Bioinorganic Catalysis; Reedijk, J., Bouwman, E., Eds.; Marcel Dekker: New York, 1999; p 423.
12. 12: Banerjee, R., Ed.; J. Wiley & Sons: New York, 1999. Pratt, J. M. In Metal Ions in Biological Systems; Sigel, H., Sigel, A., Eds.; Marcel Dekker Inc.: New York, 1993; Vol. 29, p 229. Marzilli, L. In Bioinorganic Catalysis; Reedijk, J., Bouwman, E., Eds.; Marcel Dekker: New York, 1999; p 423.
13. Marques, H. M.; Warden, C.; Hicks, R. P.; Brown, K. L. J. Chem. Soc. 1996, 27. Marques, H. M.; Brown, K. L. J. Mol. Struct. 1995, 340, 97. Marques, H. M.; Hicks, R. P.; Brown, K. L. Chem. Commun. (Cambridge) 1996, 1427 and references therein.
14. Marques, H. M.; Warden, C.; Hicks, R. P.; Brown, K. L. J. Chem. Soc. 1996, 27. Marques, H. M.; Brown, K. L. J. Mol. Struct. 1995, 340, 97. Marques, H. M.; Hicks, R. P.; Brown, K. L. Chem. Commun. (Cambridge) 1996, 1427 and references therein.
15. Marques, H. M.; Warden, C.; Hicks, R. P.; Brown, K. L. J. Chem. Soc. 1996, 27. Marques, H. M.; Brown, K. L. J. Mol. Struct. 1995, 340, 97. Marques, H. M.; Hicks, R. P.; Brown, K. L. Chem. Commun. (Cambridge) 1996, 1427 and references therein.
16. Hansen, L. M.; Derecskei-Kovacs. A.; Marynick, D. S. J. Mol. Struct. 1998, 431, 53 and references therein.
17. Kratky, C.; Färber, G.; Gruber, K.; Deuter, Z.; Nolting, H. F.; Konrat, R.; Kräutler, B. J. Am. Chem. Soc. 1995, 117, 4654.
18. Brown, K. L.; Cheng, S.; Zubkowski, J. D.; Valente, E. J.; Kropton, L.; Marques, H. M. Inorg. Chem. 1997, 36, 3666.
19. Randaccio, L.; Geremia, S.; Furlan, M.; Slouf, M. Inorg. Chem. 1998, 37, 5390.
20. Furlan, M., Ph.D. Thesis, University of Trieste, 1999.
21. Randaccio, L.; Geremia, S.; Nardin, G.; Slouf, M.; Srnova, I. Inorg. Chem. 1999, 38, 4087.
22. 12-Proteins; Kräutler, B., Arigoni, D., Golding, B. T., Eds.; Wiley-VCH: Weinheim, 1998; p 133.
23. 12-Proteins; Kräutler, B., Arigoni, D., Golding, B. T., Eds.; Wiley-VCH: Weinheim, 1998; p 133.
24. 12-Proteins; Kräutler, B., Arigoni, D., Golding, B. T., Eds.; Wiley-VCH: Weinheim, 1998; p 320 and references therein.
25. Bouquiere, J. P.; Finney, J. L.; Savage H. F. J. Acta Crystallogr. 1994, B50, 566. Bouquiere, J. P.; Finney, J. L.; Lehmann, M. S.; Lindley, P. F.; Savage H. F. J. Acta Crystallogr, 1993, B49, 79. Savage, H. F. J. Biophys. 1986, 50, 947, 967. Savage, H. F. J.; Finney, J. L. Nature 1986, 322, 717.
26. Bouquiere, J. P.; Finney, J. L.; Savage H. F. J. Acta Crystallogr. 1994, B50, 566. Bouquiere, J. P.; Finney, J. L.; Lehmann, M. S.; Lindley, P. F.; Savage H. F. J. Acta Crystallogr, 1993, B49, 79. Savage, H. F. J. Biophys. 1986, 50, 947, 967. Savage, H. F. J.; Finney, J. L. Nature 1986, 322, 717.
27. Bouquiere, J. P.; Finney, J. L.; Savage H. F. J. Acta Crystallogr. 1994, B50, 566. Bouquiere, J. P.; Finney, J. L.; Lehmann, M. S.; Lindley, P. F.; Savage H. F. J. Acta Crystallogr, 1993, B49, 79. Savage, H. F. J. Biophys. 1986, 50, 947, 967. Savage, H. F. J.; Finney, J. L. Nature 1986, 322, 717.
28. Bouquiere, J. P.; Finney, J. L.; Savage H. F. J. Acta Crystallogr. 1994, B50, 566. Bouquiere, J. P.; Finney, J. L.; Lehmann, M. S.; Lindley, P. F.; Savage H. F. J. Acta Crystallogr, 1993, B49, 79. Savage, H. F. J. Biophys. 1986, 50, 947, 967. Savage, H. F. J.; Finney, J. L. Nature 1986, 322, 717.
29. (a) Mancia, F.; Keep. N. H.; Nakagawa, A.; Leadlay, P. F.; McSweeney, S.; Rasmusssen, B.; Boske, P.; Diat, O.; Evans, P. R. Structure 1996, 4, 339. Mancia, F.; Evans, P. R. Structure 1998, 6, 771.
30. (a) Mancia, F.; Keep. N. H.; Nakagawa, A.; Leadlay, P. F.; McSweeney, S.; Rasmusssen, B.; Boske, P.; Diat, O.; Evans, P. R. Structure 1996, 4, 339. Mancia, F.; Evans, P. R. Structure 1998, 6, 771.
31. (b). Drennan, C. L.; Huang, S.; Drummond, J. T.; Matthews, R. G.; Ludwig, M. L. Science 1994, 266, 1669. Dixon, M.; Huang, S.; Mattews, R. G. Structure 1996, 4, 1263.
32. (b). Drennan, C. L.; Huang, S.; Drummond, J. T.; Matthews, R. G.; Ludwig, M. L. Science 1994, 266, 1669. Dixon, M.; Huang, S.; Mattews, R. G. Structure 1996, 4, 1263.
33. (a) Shibata, N.; Mesuda, J.; Tobimatsu, T.; Toraya, T.; Suto, K.; Morimoto, Y.; Yasuoka, N. Structure 1999, 7, 997.
34. (b) Toraya, T.; Sugimoto, Y.; Tamao, Y.; Shimizu, S.; Fukui, S. Biochemistry 1971, 10, 3475.
35. Otwinowski, Z.; Minor, W. Methods Enzymol. 1996, 276, 307.
36. Sheldrick, G. M. SHELXL-97; Universität Göttingen: Göttingen, 1997.
37. 12-Proteins; Kräutler, B., Arigoni, D., Golding, B. T., Eds.; Wiley-VCH: Weinheim, 1998; p 335.
38. Wagner, T.; Afshar, C. E.; Carell, H. L.; Glusker, J. P.; Englert, U.; Hogekamp, H. P. C. Inorg. Chein. 1999, 38, 1784.
39. Kräutler, B.; Konrat, R.; Stupperich, E.; Färber, G.; Graber, K.; Kratky, C. Inorg. Chem. 1994, 33, 4128.
40. Stasrikov, E. B.; Stener, T. Acta Crystallogr. 1998, B54, 94.
41. Recent Developments and Applications of Modern Density Functional Theory; Seminario, M., Ed.; Elsevier: Amsterdam, 1996.
42. Toffoli, D. Thesis, University of Trieste, Italy, 1999.
43. Hohenester, E.; Kratky, C.; Kräutler, B. J. Am. Chem. Soc. 1991, 113, 4523.
44. Randaccio, L.; Geremia, S.; Zangrando, E.; Ebert, C. Inorg. Chem. 1994, 33, 4641 and references therein.
45. Geremia, S.; Randaccio, L.; Zangrando, E. Gazz. Chim. Ital. 1992, 122, 229.
46. 3Cbl, when data are collected at 100 and 275 K.
47. (a) Brown, K. L.; Gupta, B. D. Inorg. Chem, 1990, 29, 3854.
48. (b) Brown, K. L.; Satyanarayana, S. Inorg. Chem. 1992, 31, 1366.
49. 12; Banerjee, R., Ed.; J. Wiley & Sons: New York, 1999; p 73.
50. Attia, W. M.; Zangrando, E.; Randaccio, L.; Antolini, L.; Lopez, C. Acta Crystallogr. 1989, C45, 1500.
51. Lexa, D.; Saveant, J. M. J. Am. Chem. Soc. 1978, 100, 3220.
52. Sheperd, R. E.; Zhang, S.; Dowd, P.; Choi, G.; Wick, B.; Choi, S. Inorg. Chim. Acta 1990, 174, 249.
53. Peressini, S. Private communication.
54. Brown, K. L.; Evans, D. R.; Zubkowski, J. D.; Valente, E. J. Inorg. Chem. 1996, 35, 415. Xou, X.; Brown, K. L. Inorg. Chim. Acta 1998, 267, 305.
55. Brown, K. L.; Evans, D. R.; Zubkowski, J. D.; Valente, E. J. Inorg. Chem. 1996, 35, 415. Xou, X.; Brown, K. L. Inorg. Chim. Acta 1998, 267, 305.
56. Calafat, A. M.; Marzilli, L. G. J. Am. Chem. Soc. 1993, 115, 9182.
57. 12-Proteins; Kräutler, B., Arigoni, D., Golding, B. T., Eds.; Wiley-VCH: Weinheim, 1998; p 349. Tollinger, M.; Konrat, R.; Kräutler, B. Helv. Chim. Acta 1999, 82, 158.
58. 12-Proteins; Kräutler, B., Arigoni, D., Golding, B. T., Eds.; Wiley-VCH: Weinheim, 1998; p 349. Tollinger, M.; Konrat, R.; Kräutler, B. Helv. Chim. Acta 1999, 82, 158.
59. Brown, K. L.; Marques, H. M. J. Mol. Struct. (THEOCHEM) 1998, 453, 209.