Vitamin B12: Unique metalorganic compounds and the most complex vitamins

Molecules

Volumn 15, Issue 5, 2010, Pages 3228-3259

  Randaccio, Lucio ^a   Geremia, Silvano ^a   Demitri, Nicola ^a   Wuerges, Jochen ^a  

^a UNIVERSITY OF TRIESTE   (Italy)

Author keywords

B12 enzymes; B12 structure function; B12 transport proteins; Cobalamins; Vitamin B12

Indexed keywords

CYANOCOBALAMIN; ORGANOMETALLIC COMPOUND;

CHEMISTRY; HUMAN; REVIEW; STRUCTURE ACTIVITY RELATION; TRANSPORT AT THE CELLULAR LEVEL;

BIOLOGICAL TRANSPORT; HUMANS; ORGANOMETALLIC COMPOUNDS; STRUCTURE-ACTIVITY RELATIONSHIP; VITAMIN B 12;

EID: 77952803052     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules15053228     Document Type: Review

References (87)

1. Folkers, K. History of Vitamin B12: Pernicious Anemia to Crystalline Cyanocobalamin. In Vitamin B12; Dolphin, D., Ed.; John Wiley & Sons: New York, NY, USA, 1982; Volume I, pp. 1-15.
2. Hodgkin, D.C. New and Old Problem in the Structure Analysis of Vitamin B12. In Vitamin B12, Proceedings of the Third European Symposium on Vitamin B12 and Intrinsic Factors, Zurich, Switzerland, March 1999; Zagalak, B., Friedrich, W., Eds.; Walter de Gruyter: Berlin, Germany, 1979; pp. 19-36.
3. Woodward, R.B. Synthetic vitamin B12. In Vitamin B12, Proceedings of the Third European Symposium on Vitamin B12 and Intrinsic Factors, Zurich, Switzerland, March 1999; Zagalak, B., Friedrich, W., Eds.; Walter de Gruyter: Berlin, Germany; 1979, pp. 37-88.
4. Kräutler, B. Vitamin B12 and B12 Proteins, Kräutler, B., Arigoni, D., Golding, B.T., Eds.; Wiley-VCH: Weinheim, Germany, 1998; pp. 3-43.
5. Hogenkamp, H.P.C. Chemistry and Biochemistry of B12; Banerjee, R., Ed.; John Wiley & Sons; New York, NY, USA, 1999; pp. 3-8.
6. Brown, K.L. Chemistry and Enzymology of Vitamin B12. Chem. Rev. 2005, 105, 2075-2149.
7. Kräutler, B. Organometallic Chemistry of B12 Coenzymes. In Metal Ions in Life Sciences; Sigel A., Sigel H., Sigel, R.K.O., Eds.; Royal Society of Chemistry: Cambridge, UK, 2009; Volume 6, pp. 1-51.
8. Matthews R.G. Cobalamin- and Corrinoid-Dependent Enzymes. In Metal Ions in Life Sciences; Sigel, A.; Sigel, H.; Sigel, R.K.O., Eds.; Royal Society of Chemistry: Cambridge, UK, 2009; Volume 6, pp. 53-114.
9. Battersby, A.R.; Leeper, F.J. Biosynthesis of B12 in the aerobic organism Pseudomonas denitrificans. In Chemistry and Biochemistry of B12; Banerjee, R., Ed.; John Wiley & Sons; New York, NY, USA, 1999; pp. 507-535.
10. Scott, A.I.; Roessner, C.A.; Santader, P.J. B12 Biosynthesis: the anaerobic pathway. In Chemistry and Biochemistry of B12; Banerjee, R., Ed.; John Wiley & Sons; New York, NY, USA, 1999; pp. 537-556.
11. Randaccio, L.; Geremia, S.; Wuerges, J. Crystallography of Vitamin B12 Proteins. J. Organometal. Chem. 2007, 692, 1198-1215.
12. Fedosov, S.N.; Fedosova, N.U.; Kräutler; B., Nexø E.; Petersen, T.E. Mechanisms of discrimination between cobalamins and their natural analogues during binding to the specific B12-transporting proteins. Biochemistry 2007, 46, 6446-6458 and references therein.
13. Wuerges, J.; Garau, G.; Geremia, S.; Fedosov, S.N.; Petersen, T.E.; Randaccio, L. Structural basis for mammalian vitamin B12 transport by transcobalamin. Proc. Natl. Acad. Sci. USA 2006, 103, 4386-4391.
14. Mathews, F.S.; Gordon, M.M.; Chen, Z.; Rajashankar, K.R.; Ealick, S.E.; Alpers, D.H.; Sukumar, N. Crystal structure of human intrinsic factor: cobalamin complex at 2.6-Å resolution. Proc. Natl. Acad. Sci. USA 2007, 104, 17311-17316.
15. Russell-Jones, G.; McTavish, K.; McEwan, J.; Rice J.; Novotnik D. Vitamin-mediated targeting as a potential mechanism to increase drug uptake by tumours. J. Inorg. Biochem. 2004, 98, 1625-1633.
16. Waibel, R.; Treichler, H.; Schaefer, N.G.; van Staveren, D.R.; Mudwiler, Kunze, S.; Küenzi, M.; Alberto, R.; Nüesch, J.; Knuth, A.; Moch, H.; Schibli, R.; Shubiger, P.A. New Derivatives of Vitamin B12 Show Preferential Targeting of Tumours. Cancer Res. 2008, 68, 2904-2911.
17. Petrus, A.K.; Fairchild, T.J.; Doyle, R.P. Travelling the Vitamin B12 Pathway: Oral Delivery of Protein and Peptide Drugs. Angew. Chem. Int. Ed. 2009, 48, 1022-1028.
18. Ragsdale, S.W. The acetogenic corrinoid proteins. In Chemistry and Biochemistry of B12; Banerjee, R., Ed.; John Wiley & Sons; New York, NY, USA, 1999; pp. 633-653.
19. Sauer, K.; Thauer, R.K. The role of corrinoids in methanogenesis. In Chemistry and Biochemistry of B12; Banerjee, R., Ed.; John Wiley & Sons; New York, NY, USA, 1999; pp. 655-680.
20. Koutmos, M.; Pejchal, R.; Bomer, T.M.; Matthews, R.G.; Smith, J.L.; Ludwig, M.L. Metal active site elasticity linked to activation of homocysteine in methionine synthase. Proc. Natl. Acad. Sci. USA 2008, 105, 3286-3291.
21. Fontecave, M.; Mulliez, E. Ribonucleotide reductases. In Chemistry and Biochemistry of B12; Banerjee, R., Ed.; John Wiley & Sons; New York, NY, USA, 1999; pp. 731-756.
22. Wolhfarth, G.; Diekert, G. Reductive dehalogenases. In Chemistry and Biochemistry of B12; Banerjee, R., Ed.; John Wiley & Sons; New York, NY, USA, 1999; pp. 871-893.
23. Butler, P.; Ebert, M.O.; Lyskowski, A.; Gruber, K.; Kratky, C.; Kräutler B. Vitamin B12: A Methyl Group without a Job? Angew. Chem. Int. Ed. 2006, 45, 989-993.
24. Randaccio, L. Vitamin B12 Coenzyme Models: Perspectives on Recent Developments in the Chemistry of the Cobaloximes and Related Models. Comments Inorg. Chem. 1999, 21, 327-376 and references therein.
25. Randaccio, L.; Geremia, S.; Nardin, G., Wuerges, J. X-ray structural chemistry of cobalamins. Coord. Chem. Rev. 2006, 250, 1332-1350.
26. Hogenkamp, H.P.C. Reactions of Alkyl Ligands Coordinated to Cobalamins and Cobaloximes. In Vitamin B12; Dolphin, D., Ed.; John Wiley & Sons: New York, NY, USA, 1982; Volume I, pp. 295-323.
27. Luo, L.B.; Li, G.; Chen, H.L.; Fu, S.W.; Zhang, S.Y. Laser-induced photoacoustic calorimetric determination of enthalpy and volume changes in photolysis of 5′-deoxyadenosylcobalamin and methylcobalamin. J. Chem. Soc. Dalton Trans. 1998, 2103-2107. (Pubitemid 128756625)
28. Randaccio, L.; Geremia, S.; Demitri, N.; Wuerges, J. Structural aspects of B12 chemistry and biochemistry: From simple models to proteins. Trends Inorg. Chem. 2009, 11, 1-19.
29. Hannibal, L.; Smith, C.A.; Chavez, R.A.; Jacobsen, D.W.; Brasch, N.E Nitroxylcob(III)alamin: Synthesis and X-ray Structural Characterization. Angew. Chem. Int. Ed. 2007, 46, 5140-5143.
30. Brasch, N.E.; Kent State University, Kent, USA, Personal communication, 2009.
31. Hannibal, L.; Smith, C.A.; Smith, J.A.; Axhemi, A.; Miller, A.; Wang, S.; Brasch, N.E; Jacobsen, D.W. High Resolution Crystal Structure of the Methylcobalamin Analogues Ethylcobalamin and Butylcobalamin by X-ray Synchrotron Diffraction. Inorg. Chem. 2009, 48, 6615-6622.
32. Hassanin, H.A.; Hannibal, Jacobsen, D.W.; Brown, K.L.; Marques, M.M.; Brasch, N.E NMR spectroscopy and molecular modelling studies of nitrosylcobalamin: further evidence that the deprotonated, base-off form is important for nitrosylcobalamin in solution. Dalton Trans. 2009, 424-433.
33. Kuta, J; Wuerges, J; Randaccio, L.; Kozlowski, P.M. Axial Bonding in Alkylcobalamins: DFT Analysis of the Inverse versus Normal Trans Influence. J. Phys. Chem. A 2009, 113, 11604-11612.
34. Brown, K.L.; Peck-Siler, S. Heteronuclear NMR Studies of Cobalamins. 9. Temperature-Dependent NMR of Organocobalt Corrin Enriched in 13 C in the Organic Ligand and the Thermodynamics of Base-On/Base-Off Reactions. Inorg. Chem. 1988, 27, 3548-3555.
35. Pratt, J.M. The Roles of Co, Corrins, and Protein. I. Co-Ligand Bonding and the Trans Effect. In Chemistry and Biochemistry of B12; Banerjee, R., Ed.; John Wiley & Sons; New York, NY, USA, 1999; pp. 73-112.
36. Alpers, D.H.; Russel-Jones, G.J. Intrinsic factor, haptocorrin and their receptors. In Chemistry and Biochemistry of B12; Banerjee, R., Ed.; John Wiley & Sons; New York, NY, USA, 1999; pp. 411-440.
37. Rothenberg, S.P.; Quadros, E.V.; Regec, A. Transcobalamin II. In Chemistry and Biochemistry of B12; Banerjee, R., Ed.; John Wiley & Sons; New York, NY, USA, 1999; pp. 441-473.
38. Andersen, C.B.; Madsen, M.; Storm, T.; Moestrup, S.K.; Andersen, G.R. Structural basis for receptor recognition of vitamin-B12-intrinsic factor complexes. Nature 2010, 464, 445-449.
39. Nexø, E. Cobalamin Binding Proteins. In Vitamin B12 and B12 Proteins; Kräutler, B., Arigoni, D., Golding, B.T., Eds.; Wiley-VCH: Weinheim, Germany, 1998; pp. 461-471.
40. Quadros, E.V.; Nakayama, Y.; Sequeira, J.M. The protein and the gene encoding the receptor for the cellular uptake of transcobalamin-bound cobalamin. Blood 2009, 113, 186-192.
41. Banerjee, R. B12 Trafficking in Mammals: A Case for Coenzyme Escort Service. ACS Chem. Bio. 2006, 1, 149-159.
42. Banerjee, R; Gherasim, C.; Padovani, D. The tinker, tailor, soldier in intracellular B12 trafficking, Curr. Opin. Chem. Biol. 2009, 13, 484-491
43. Bradbeer, C. Cobalamin Transport in Bacteria. In Chemistry and Biochemistry of B12; Banerjee, Ed.; John Wiley & Sons; New York, NY, USA, 1999; pp. 489-506.
44. Fedosov, S.N.; Berglund; L., Fedosova, N.U.; Nexø, E.; and Petersen, T.E. Comparative analysis of cobalamin binding kinetics and ligand protection for intrinsic factor, transcobalamin, and haptocorrin. J. Biol. Chem. 2002, 277, 9989-9996.
45. Wuerges, J.; Geremia, S.; Randaccio, L. Structural study on ligand specificity of human vitamin B12 transporters. Biochem. J. 2007, 403, 431-440.
46. Fedosov, S.N.; Fedosova, N.U.; Berglund; Moestrup, S.K.; Nexø, E.; Petersen, T.E. Composite Organization of the Cobalamin Binding and Cubilin Recognition Sites of Intrinsic Factor. Biochemistry 2005, 44, 3604-3614.
47. Wuerges, J.; Geremia, S.; Fedosov, S.N.; Randaccio, L. Vitamin B12 Transport Proteins: Crystallographic Analysis of γ-Axial Ligand Substitution in Cobalamin Bound to Transcobalamin. IUBMB Life 2007, 59, 722-729.
48. Hogenkamp, H.P.; Collins, D.A.; Grissom, C.B., West, F.G. Diagnostic and Therapeutic Analogues of Cobalamins. In Chemistry and Biochemistry of B12; Banerjee, R., Ed.; John Wiley & Sons; New York, NY, USA, 1999; pp. 385-410.
49. Chimento, D.P.; Mohanty, A.K.; Kadner, R.J.; Wiener, M.C. Substrate-induced transmembrane signalling in the cobalamin transporter BtuB. Nature Struct. Biol. 2003, 10, 394-400.
50. Shultis, D.D.; Purdy, M.D.; Banchs, C.N.; Wiener, M.C. Outer Membrane Active Transport: Structure of the BtuB:TonB Complex. Science 2006, 312, 1396-1399.
51. Locher, K.P.; Lee, A.T.; Rees, D.C. The E. coli BtuCD Structure: a Framework for ABC Transporter Architecture and Mechanism. Science 2002, 296, 1091-1098.
52. Karpowich, N.K.; Huang, H.H.; Smith, P.C.; Hunt, J.F. Crystal Structures of the BtuF Periplasmatic-binding Protein for Vitamin B12 Suggest a Functionally Important Reduction in Protein Mobility upon Ligand Binding. J. Biol. Chem. 2003, 278, 8429-8434.
53. Borths, E.L.; Locher, K.P.; Lee, A.T.; Rees, D.C. The structure of Escherichia coli BtuF and binding its cognate ATP binding cassette transporter. Proc. Natl. Acad. Sci. USA 2002, 99, 016642-16647.
54. Hvorup, R.N.; Goetz, B.A.; Niederer, M.; Hollenstein, K.; Perozo, E.; Locher, K.P. Asymmetry in the Structure of the ABC Transporter-Binding Protein Complex BtuCD-BtuF. Science 2007, 317, 1387-1390. (Pubitemid 47417478)
55. Drennan, C.L.; Huang, S.; Drummond, J.T.; Mattews, R.G.; Ludwig, M.L. How a protein binds B12: A 3.0 X-ray structure of B12-binding domain of methionine synthase. Science 1994, 266, 1699-1704.
56. Mancia, F.; Keep, N.H.; Nakagawa, A.; Leadlay, P.F.; McSweeney, S.; Rasmussen, B.; Bösecke, P; Diat, O.; Evans, P.R. How coenzyme B12 radicals are generated: the crystal structure of methylmalonyl-coenzyme A mutase at 2 Å resolution. Structure 1996, 4, 339-350.
57. Evans, J.C.; Huddler, D.P.; Hilgers, M.T.; Romanchuk, G.; Matthew, R.G.; Ludwig, M.L. Structures of the N-terminal modules imply large domain motions during catalysis by methionine synthase. Proc. Natl. Acad. Sci. USA 2004, 101, 3729-3736.
58. Koutmos, M.; Pejchal, R.; Bomer, T.M.; Matthew, R.G.; Smith, J.L.; Ludwig, M.L. Metal active site elasticity linked to activation of homocystine in methionine synthase. Proc. Natl. Acad. Sci. USA 2008, 105, 3286-3291.
59. March, E.N.G.; Holloway, D.E. Cloning and sequencing of glutamate mutase component S from Clostridium tetanomorphum. FEBS Lett. 1992, 310, 167-170.
60. Bandarian, V.; Pattridge, K.A.; Lennon, B.W.; Huddler, D.P.; Matthews, R.G.; Ludwig, M.L. Domain alternation switches B12-dependent methionine synthase to the activation conformation. Nat. Struct. Biol. 2002, 9, 53-56.
61. Datta, S., Koutmos, M., Pattridge, K.A., Ludwig, M.L., Matthew, R.G. A disulfide-stabilized conformer of methionine synthase reveals an unexpected role for the histidine ligand of the cobalamin cofactor. Proc. Natl. Acad. Sci. USA 2008, 105, 4115-4120.
62. Bandarian, V.; Matthews, R.G.; Ludwig, M.L. Factors modulating conformational equilibria in large modular proteins: A case study with cobalamin-dependent methionine synthase. Proc. Natl. Acad. Sci. USA 2003, 100, 8156-8163.
63. Fleischhacker, A.S.; Matthews, R.G. Ligand Trans Influence Governs Conformation in Cobalamin-Dependent Methionine Synthase. Biochemistry, 2007, 46, 12382-12392.
64. Hagemeier, C.H.; Krüer, M.; Thauer, R.K.; Warkentin, B.; Ermler, U. Insight into the mechanism of biological methanol activation based on the crystal structure of the methanol-cobalamin methyltransferase complex. Proc. Natl. Acad. Sci. USA 2006, 103, 18917-18922.
65. Sauer, K.; Thauer, R.K. The Role of Corrinoids in Methanogenesis. In Chemistry and Biochemistry of B12; Banerjee, R., Ed.; John Wiley & Sons; New York, NY, USA, 1999; pp. 655-679.
66. Svetlitchnaia, T.; Svetlitchnyi, V.; Meyer, O.; Dobbek, H. Structural insights into methytransfer reactions of a corrinoid iron-sulfur protein involved in acetyl-CoA synthesis. Proc. Natl. Acad. Sci. USA 2006, 103, 14331-14336.
67. Randaccio, L.; Bresciani-Pahor, N.; Zangrando, E.; Marzilli, L.G. Structural Properties of Organocobalt Coenzyme B12 Models. Chem. Soc. Rev. 1989, 18, 225-250.
68. Toraya, T. Radical catalysis of B12 enzymes: structure, mechanism, inactivation, and reactivation of diol and glycerol dehydratases. Cell. Mol. Life Sci. 2000, 57, 1006-127.
69. Banerjee, R. Radical Skeleton Rearrangements: Catalysis by Coenzyme B12-Dependent Mutases. Chem. Rev. 2003, 103, 2083-2094.
70. Toraya, T. Radical Catalysis in Coenzyme B12-Dependent Isomerization (eliminating) Reactions. Chem. Rev. 2003, 103, 2095-2127.
71. Frey, P.A.; Essenberg, M.K.; Abeles, R.H. Studies on the Mechanism of Hydrogen Transfer in the Cobamide Coenzyme-dependent Dioldehydratase Reaction. J. Biol. Chem. 1967, 242, 5369-5377.
72. Retey, J.; Arigoni, D. Coenzym B12 als gemeinsamer Wassestoffü berträger der Dioldehydratase-und der Methylmalonyl-CoA-mutase-Reaktion. Experientia 1966, 22, 783-784.
73. Sintchak, M.D.; Arjara, G.; Kellog, B.A.; Stubbe, J.; Drennan, C.L. The crystal structure of class II ribonucleotide reductase reveals how an allosterically regulated monomer mimics a dimer. Nature Struct. Biol. 2002, 9, 293-300.
74. Buckel, W.; Golding, B.T.; Kratky, C. Stabilisation of Methylene Radicals by Cob(II)alamin in Coenzyme B12 dependent Mutases. Chem. Eur. J. 2006, 12, 352-362.
75. Kozlowski, P.M.; Kamachi, T.; Toraya, T.; Yoshizawa, K. Does Cob(II)alamin Act as a Conductor in Coenzyme B12 Dependent Mutases. Angew. Chem. Int. Ed. 2007, 46, 980-983.
76. Kumar, M.; Kozlowski, P.M. Role of the Tyrosine Residue in the Activation of the Co-C Bond in Coenzyme B12-Dependent Enzymes: Another Case of Proton-Coupled Electron Transfer. J. Phys.Chem. B 2009, 113, 9050-9054.
77. Rosenblatt, D.S.; Fenton, W.A. Methylmalonyl-CoA mutase. In Chemistry and Biochemistry of B12; Banerjee, R., Ed.; John Wiley & Sons; New York, NY, USA, 1999; pp. 367-384.
78. Stich, T.A.; Buan, N.R.; Escalante-Semerena, J.C.; Brunold, T.C. Spectroscopic and Computational Studies of the ATP:Corrinoid Adenosyltransferase (CobA) from Salmonella enterica: Insights into the Mechanism of Adenosylcobalamin Biosynthesis. J. Am. Chem. Soc. 2005, 127, 8710-8719.
79. Schubert, H.L.; Hill, C.P. Structure of ATP-bound human ATP: Cobalamin Adenosyltransferase. Biochemistry 2006, 45, 15188-15196.
80. St. Maurice, M.; Mera, P.E.; Taranto, M.P.; Sesma, F.; Escalante-Semerena, J.; Rayment, I. Structural characterization of the active site of the PduO-type ATP:Co(I)rrinoid Adenosyltransferase from Lactobacillus reuteri. J. Biol. Chem. 2007, 282, 2596-2605.
81. Maurice, M.; Mera, P.; Park, K.; Brunold, T.C.; Escalante-Semerena, J.; Rayment, I. Structural Characterization of a Human-Type Corrinoid Adenosyltransferase Confirms that Coenzyme B12 is synthesized trough a Four-Coordinate Intermediate. Biochemistry 2008, 47, 5755-5766.
82. Mera, P.E.; Maurice, M.; T.C.; Rayment, I.; Escalante-Semerena, J. Residue Phe112 of the Human-Type Corrinoid Adenosyltransferase (PduO) Enzyme of Lactobacillus reuteri Is Critical to the formation of the Four-Coordinate Co(II) Corrinoid Substrate and to the Activity of the Enzyme. Biochemistry 2009, 48, 3138-3145.
83. Petrus, A.K.; Fairchild, T.J.; Doyle, R.P. Traveling the Vitamin B12 Pathway: Oral Delivery of Protein and Peptide Drugs. Angew. Chem. Int. Ed. 2009, 48, 1022-1028.
84. Petrus, A.K.; Allis, D.G.; Smith, P.R.; Fairchild, T.J.; Doyle, R.P. Exploring the Implications of Vitamin B12 Conjugation to Insulin on Insulin Receptor Binding. ChemMedChem 2009, 4, 421-426.
85. Gupta, Y.; Kohli, D.V.; Jain, S.D. Vitamin B12-mediated transport: a potential tool for tumor targeting of antineoplastic drugs and imaging agents. Crit. Rev. Ter. Drug Carrier Syst. 2008, 25, 347-379.
86. 3+Ions to Tumour Cells by Vitamin B12 Bioconjugates. Chem. Eur. J. 2009, 15, 7980-7989.
87. Viola-Villegas, N; Rabideau, A.E.; Bartholoma, M.; Zubieta, J.; Doyle, R.P. Targeting the Cubilin Receptor through the Vitamin B12 Uptake Pathway: Cytotoxicity and Mechanistic Insight through Fluorescent Re(I) Delivery. J. Med. Chem. 2009, 52, 5253-5261.