Probing the mechanism of coenzyme B12: Synthesis, crystal structures, and molecular modeling of coenzyme B12 model compounds

Comments on Inorganic Chemistry

Volumn 23, Issue 6, 2002, Pages 385-400

  Pett, Virginia B ^a   Fischer, Anne E ^a   Dudley, Gary K ^a   Zacharias, David E ^b  

^a 931 College Mall   (United States)

^b FOX CHASE CANCER CENTER   (United States)

Author keywords

B12; Coenzyme B12; Deoxyadenosylcobalamin

Indexed keywords

COBALT; COBALT COMPLEX; COBAMAMIDE; LIGAND; NITROGEN;

ARTICLE; CALCULATION; CHEMICAL BOND; COMPLEX FORMATION; CRYSTAL STRUCTURE; DENSITY; DRUG SYNTHESIS; ELECTRON; EMPIRICISM; MOLECULAR MODEL;

EID: 0036877037     PISSN: 02603594     EISSN: None     Source Type: Journal    
DOI: 10.1080/02603590216080     Document Type: Article

References (51)

1. 12, ed. R. Banerjee, 343-365. New York: Wiley.
2. 12, ed. R. Banerjee, 3-8. New York: Wiley.
3. 12. Nature (London) 178, 64-66.
4. Lenhert, P.G., and D.C. Hodgkin. 1961. Structure of the 5,6-dimethylbenzimidazolylcobamide coenzyme. Nature (London) 192, 937-938.
5. 12 coenzyme: Methylcobalamin studies by X-ray and NMR methods. J. Am. Chem. Soc. 107, 1729-1738.
6. (a) Kovacs, J.A., Shoner, S.C., and J.J. Ellison. 1995. Metal-carbon bonds in nature. Science 270:587-588.
7. (b) Kumar, M., Qiu, D., Spiro, T.G., and S.W. Ragsdale. 1995. A methylnickel intermediate in a bimetallic mechanism of acetyl-coenzyme A synthesis by anaerobic bacteria. Science 270, 628-630.
8. 12-binding domains of methionine synthase. Science 266, 1669-1674.
9. 12 radicals are generated: The crystal structure of methylmalonyl-coenzyme A mutase at 2 Å resolution. Structure 4, 339-350.
10. (b) Mancia, F. and P.R. Evans. 1998. Conformational changes on substrate binding to methylmalonyl-CoA mutase and new insights into the free radical mechanism. Structure 6, 711-720.
11. (c) Mancia, F., Smith, G.A., and P.R. Evans. 1999. Crystal structure of substrate complexes of methylmalonyl-CoA mutase. Biochemistry 38, 7999-8005.
12. 12-dependent enzyme provides new mechanistic insights. Structure 7, 891-902.
13. 12 dependent enzyme glutamate mutase. Angew. Chem. Int. Ed. 40, 3377-3380.
14. 12 binding and the direct participation of a potassium ion in enzyme catalysis: X-ray structure of diol dehydratase. Structure 7, 997-1008.
15. 12-dependent diol dehydratases. J. Mol. Catal. B10, 87-106.
16. 12. J. Inorg. Biochem. 83, 121-132.
17. Matthews, R.G. 2001. Cobalamin-dependent methyltransferases. Acc. Chem. Res. 34, 681-689.
18. 12-dependent methylmalonyl-CoA mutase. Biochemistry 39, 7998-8006.
19. 12 models. Chem. Soc. Rev. 18, 225-250.
20. 12, vol. 1, ed. D. Dolphin, 23-106. New York: Wiley.
21. Pett, V.B., Liebman, M.N., Murray-Rust, P., Prasad, K., and J.P. Glusker. 1987. Conformational variability of corrins: Some methods of analysis. J. Am. Chem. Soc. 109, 3207-3215.
22. 12-Proteins, ed. B. Kräutler, D. Arigoni, and B.T. Golding, 335-347. New York: Wiley.
23. 12? J. Am. Chem. Soc. 109, 1238-1240.
24. 12. Bull. Soc. Chim. Fr. no. 2, 187-191.
25. 2O. Acta Cryst. B43, 280-295.
26. 12 coenzyme at 15 K. Acta Cryst. B49, 79-89.
27. 12, ed. R. Banerjee, 9-41. New York: Wiley.
28. 12, ed. R. Banerjee, 73-112. New York: Wiley.
29. 12, ed. R. Banerjee, 113-164. New York: Wiley.
30. Choo, P.L., Mulichak, A.M., Jones, Jr., R.W., Bacon, J.W., Pett, V.B., and D.E. Zacharias. 1990. A new type of organocobalt complex with a buckled equatorial ligand. Inorg. Chim. Acta. 171, 183-192.
31. McFarland, C.A., Gross, S.A., Winfield, J.S., and V.B. Pett. 1994. An ethyl-cobalt complex with a buckled equatorial ligand. Inorg. Chim. Acta. 221, 35-40.
32. Jaynes, B.S., Ren, T., Masschelein, A., and S.J. Lippard. 1993. Stereochemical control of reactivity in Co(III) alkyl complexes of the tropocoronand ligand system. J. Am. Chem. Soc. 115, 5589-5599.
33. 12: Finding the smoking gun. American Crystallographic Association Annual Meeting, Los Angeles, presentation 02.01.09.
34. (b) Pett, V.B., Fischer, A.E., Dudley, G.K., and S.O. Majors. To be submitted for publication. Cambridge Crystallographic Data Centre deposition number 189472.
35. 12 dependent diol dehydratase. 2. A kinetic and mechanistic study focusing upon the cobalt participation or nonparticipation question. J. Am. Chem. Soc. 105, 7605-7617.
36. 12. J. Am. Chem. Soc. 103, 5558-5566.
37. Marsh, E.N.G. and C.L. Drennan. 2001. Adenosylcobalamin-dependent isomerases: New insights into structure and mechanism. Curr. Opinion Chem. Biol. 5, 499-505.
38. Toscano, P.J. and L.G. Marzilli. 1979. An extensive trans-effect series: The reaction of coordinated trimethyl phosphite. Inorg. Chem. 18, 421-424.
39. Appleton, T.G., Clark, H.C., and L.E. Manzer. 1973. The trans-influence: Its measurement and significance. Coord. Chem. Rev. 10, 335-422.
40. (a) Stewart, J.J.P. 1989. Optimization of parameters for semiempirical methods. I. Method. J. Computat. Chem. 10:209-220.
41. (b) Stewart, J.J.P. 1989. Optimization of parameters for semiempirical methods. II. Applications. J. Computat. Chem. 10, 221-264.
42. Hehre, W.J., Yu, J., Klunzinger, P.E., and L. Lou. 1998. A Brief Guide to Molecular Mechanics and Quantum Chemical Calculations. Irvine, CA: Wavefunction.
43. (a) Costa, G. and G. Mestroni. 1967. Tetrahedron Lett. 41, 4005.
44. (b) Costa, G., Mestroni, G., and E. de Savorgnani. 1969. Inorg. Chim. Acta. 3, 323.
45. Dong, S., Padmakumar, R., Banerjee, R., and T.G. Spiro. 1996. Resonance Raman Co-C stretching frequencies reflect bond strength changes in alkyl cobalamins, but are unaffected by trans ligand substitution. J. Am. Chem. Soc. 118, 9182-9183.
46. Dong, S., Padmakumar, R., Banerjee, R., and T.G. Spiro. 1998. Co-C force constants from resonance Raman spectra of alkylcobalamins: Insensitivity to dimethylbenzimidazole coordination. Inorg. Chim. Acta. 270, 392-398.
47. 12 axial-base chemical precedent studies. Adenosylcobinamide plus sterically hindered axial-base Co-C bond cleavage product and kinetic studies: Evidence for the dominance of axial-base transition-state effects and for Co-N(axial-base) distance-dependent, competing σ and π effects. Inorg. Chem. 38, 1697-1707.
48. 12 chemistry and its use to probe the plausibility of an axial-base-induced, ground-state corrin butterfly conformational steric effect. Inorg. Chim. Acta. 300-302, 545-555.
49. Dölker, N., Maseras, F., and A. Liedós. 2001. A density function study on the effect of the trans axial ligand of cobalamin on the homolytic cleavage of the Co-C bond. J. Phys. Chem. B105, 7564-7571.
50. 12 models. Organometallics 20, 550-556.
51. Jensen, K.P. and U. Ryde. 2002. The axial N-base has minor influence on Co-C bond cleavage in cobalamins. J. Mol. Struct. (Theochem) 585, 239-255.