Bibliography for Vitamin B12
There is a huge literature about Vitamin B12. Here
are some key references. The articles section contains some more up-todate references.
Books | Reviews | Articles | X-Ray Crystal Structure Papers for the coenzyme
Books
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"Chemistry and Biochemistry of B12 by Ruma Banerjee (Ed), John Wiley, New York, 1999.
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"Principles of Bioinorganic
Chemistry" by S.J.Lippard and J.M.Berg, , p336-343 University Science Books, Mill Valley, California, 1994
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The Biological Chemistry of the Elements, The Inorganic Chemistry of Life by J.J.R.Frausto da Silva and R.J.P.Williams,
Chapter 16, Nickel and Cobalt : remnants of Early Life?, Clarendon, Oxford, 1991.
A second edition of this seminal text has now (2001) appeared.
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"Pollution, Causes, Effects and
Control" by R.M.Harrison (Ed), , RSC, Cambridge, 1990. See p 328-325.
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Biochemistry by G.Zubay, (Ed), Chapter 11 Vitamins andCoenzymes Macmillan, New York, 1988.
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B12.Vol. 1: Chemistry and Vol. 2: Biochemistry and Medicine. by J. D.Dolphin (Ed), Wiley, New York, 1982.
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"Structural studies on molecules of biological interest - A volume in honour of Dorothy Hodgkin" by G.Dodson, J.P.Glusker and D Sayre (Eds), Clarendon, Oxford, 1981.
A comprehensive description of the background to the medicine, biology and chemistry of Vitamin B12. Includes descriptions of Dorothy Hodgkin's work through the eyes of colleagues and friends.
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"Vitamin B12 and
B12 Coenzymes" by Ei-Ichiro Ochiai, , Chapter 12, Bioinorganic Chemistry, An Introduction, Allyn and Bacon, Boston, 1977
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Inorganic Chemistry of Vitamin
B12 by J.M.Pratt, , Academic Press, New York, 1972.
Reviews
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Biosynthesis of vitamin B12 (Biosynthesis: Polyketides and Vitamins) by A.R. Battersby and F.J. Leeper,. Top. Curr. Chem., 1998, 195, 143-193.
- Vitamin B12. Recent discoveries cast new light on an ancient structure by A.I. Scott, Pure and Applied Chem., 1996, 68(11), 2057-2063
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Structural and solution properties of rhodoximes: the Rh analogs of cobaloximes, a vitamin B12 model. by L. Randaccio, Croat. Chem. Acta, 1994, 67(2), 235-40.
- The Discovery of Nature's pathway to Vitamin B12. A 25 year Odyssey by A.I.Scott, Tetrahedron, 1994, 50 (47), 13315-13333.
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How nature Synthesises Vitamin B12 - A Survey of the Last Four Billion Years by A.I. Scott, Angew. Chem., Int. Ed. 1993, 32(9), 1223-1243.
- Organometallic chemistry in Biology : the role of Vitamin B12 by J.Halpern, Bull. Soc. Chim. France, 1988, 187-191.
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Chemistry and significance of Vitamin B12 model systems by J. Halpern. D. Dolphin (Ed), B12, . 1982, 1 , 501-41. Wiley, N. Y
A review of cobalt compounds with the chemical characteristics of vitamin B12 and its derivatives. Emphasis is on redox reactions, Co-C bond formation and cleavage, and studies related to the mechanisms of B12-promoted reactions.
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Mechanism of Cobalamin-Dependent Rearrangements by B.M.Babior, Acc. Chem.Res., 1975, 8, 376 - 384.
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2001
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"Interaction of the Substrate Radical and the 5'-Deoxyadenosine-5'-Methyl Group in Vitamin B12 Coenzyme-Dependent Ethanolamine Deaminase" by K. Warncke and A. S. Utada, J. Amer. Chem. Soc., 2001, 123, 8564.
- "A Continuous Wave and Pulse EPR and ENDOR Investigation of Oxygenated Co(II)
Corrin Complexes"
S. Van Doorslaer, A. Schweiger, and
B. Kräutler, , J. Phys. Chem. B, 2001, 105, 7554.
- "Assessment of the Existence of Hyper-Long Axial Co(II)-N Bonds in Cobinamide B12 Models by Using Electron Paramagnetic
Resonance Spectroscopy"
J. S. Trommel, K. Warncke, and L. G. Marzilli, , J. Amer. Chem. Soc., 2001, 123, 3358.
- Thermodynamic and Kinetic Studies on the Reaction between the Vitamin B12b Derivative a-(N-Methylimidazolyl)cobalamin and N-Methylimidazole: Ligand Displacement at the
Axial Site of Cobalamins by A. G. Cregan,
N.E. Brasch,* and R. van Eldik, Inorg. Chem., 2001, 40
(7), 1430 -1438
2000
- A Multinuclear Solid-State NMR Analysis of Vitamin B12 in Its
Different Polymorphic Forms by
A. Medek and
L. Frydman, J.Amer.Chem.Soc., 2000, 122
(4), 684
-691 br>
Multinuclear solid-state NMR methods (59Co, 13C, 15N, and 31P NMR) were
applied at natural abundance to the structural and dynamic analysis of cyanocobalamin. 13C spectra were the most informative. Article provides a useful set of references into solid state NMR spectra of cobalamin.
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1999
- Identification of a Rearranged-Substrate, Product Radical Intermediate and the Contribution of a Product Radical Trap in Vitamin B12 Coenzyme-Dependent Ethanolamine Deaminase Catalysis by K. Warncke, J.C. Schmidt, and Shyue-Chu Ke
J. Amer.Chem. Society, 1999, 121(45), 10522-10528.
- "The Dehydration Step in the Enzyme-Coenzyme-B12 Catalysed Diol Dehydrase Reaction of 1,2-Dihydroxyethane Utilizing a Hydrogen-Bonded Carboxylic Acid Group as an Additional Cofactor: A Computational Study" by P.George, P.E.M.Siegbahn, J.P.Glusker, and C.W.Bock, , J.Phys.Chem. B, 1999, 103, 7531.
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Hydrolytic Dealkylation of Organocobaloximes Related to Coenzyme B12: Ligand Influences. by M.P.Jensen, D.M.Zinkl, and J.Halpern, Inorg. Chem., 1999, 38, 2386-2393.
1998
- Mechanism of Action of Vitamin B12. Ultrafast Radical Clocks Provide No Evidence for Radical Intermediates in Cyclopropane Models for the Methylmalonyl-CoA to Succinyl-CoA Carbon Skeleton Rearrangement, by Mu He and P. Dowd, J.Amer.Chem.Soc.,1998, 120(6), 1133-1137.
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1997
- Comparison of the Coordination Distances Derived by
Extended X-ray Absorption Fine Structure and X-ray
Crystallography in a Vitamin B12 Model by
L. Randaccio* and S.Geremia, Organometallics, 1997, 16
(23), 4951
-4953.
Communication questions the accuracy of EXAFS measurements for Co-C bond distances in models. See below, first reference.
1996
- X-ray Absorption Spectroscopic Study of "Costa Type"
Organocobalt Coenzyme B12 Models
M. Giorgetti, M. Berrettoni,
P. Conti,
A. Di Cicco,
R. Marassi, and I. Ascone, Organometallics, 1996, 15
(16), 3491-3495.
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Mechanism of Action of Vitamin B12. A New Test for Free Radical Intermediates Using a Cyclopropane Model for the Methylmalonyl-CoA to Succinyl-CoA Carbon Skeleton Rearrangement by Mu He and P.Dowd, J.Amer.Chem.Soc.,1996, 118(3), 711-711.
- "Mutations in the B12-Binding Region of Methionine Synthase: How the Protein
Controls Methylcobalamin Reactivity" by J. T. Jarrett, M. Amaratunga, C. L. Drennan,J. D. Scholten, R. H. Sands, M. L. Ludwig, and R. G. Matthews
, Biochem. , 1996, 35, 2464.
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Pre : 1996
- "How nature Builds the Pigments of Life: The Conquest of Vitamin B12, by A.R. Battersby, Science, 1994, 264, 1551-1557.
- "Binding Site Revealed of Nature's Most Beautiful Cofactor" by JoAnne Stubbe, , Science, 1994, 266, 1663.
A cogent and useful summary of the state of our understanding (in 1994) of the structure of the B12 requiring enzyme. (but see next reference)
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"How a Protein Binds B12: A 3.0 A X-ray Structure of B12-Binding Domains of
Methionine Synthase by C.L.Drennan, S. Huang, J.T. Drummond, R.G.Matthews, M.L.Ludwig, , Science, 1994, 266, 1669
- "How nature Synthesises Vitamin B12 - A survey of the Last Four Billion Years by A.I.Scott, Angew.Chem.Int. Ed., 1993, 32(9), 1223-1243.
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"The B12 Mystery" B.T.Goldring, Chemistry in Britain,1990, 950-4.
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Evidence for hydride complexes of cobalt(III) corrinoids by S.M.Chemaly and J.M.Pratt, . J. Chem. Soc., Dalton Trans., 1984, 595-9.
"Reduction of aquacobalamin and cyanoaquacobinamide with Zn dust in AcOH gave unstable yellow complexes in solution. UV-visible absorption spectra of the solns. showed the complexes to be 5-coordinate Co(III) corrinoids with H- as the axial ligand. Both reacted with
H2C:CH2 and MeCH:CH2, respectively, to give ethylcobalamin and isopropylcobinamide."
- Organometallic Chemistry in Biology: the role of Vitamin B12 by J.Halpern, Bull.Soc.Chim.France, 1988 (2), 187-191.
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EPR, ENDOR, CD, and MCD Spectra of [63Cu]Cobalamin by K.A.Robinson, J.Amer.Chem.Soc., 1979, 101(20), 6105 - 6110
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Why Does nature Not Use the Porphyrin Ligand in Vitamin B12? by J.Halpern, J.Amer.Chem.Soc., 1987, 109, 1238-1240
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T.H.Finley, J.Valinsky, K.Sato, and R.H.Abeles, J.Biol.Chem., 1972, 247, 4197.
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J.M.Wood, P.S.Kennedy and C.G.Rosen, Nature, 1968,
220, 173.
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Original paper showing that methylcobalamin can methylate mercury in sediments.
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Pentacyanocobaltate(III). A new series of stable organocobalt compounds by J.Halpern and J.P.Maher, J.Amer.Chem.Soc.,1964,86,2311.
The first cobalt alkyl complex and model for B12
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Alkylcobaloximes and their relation to alkylcobalamins. by G. N. Schrauzer, R. J.Windgassen, J. Am. Chem. Soc., 1966, 88(16), 3738-43.
Methods of preparationof the remarkably stable alkylcobaloximes RCo(Q2H2)Z (with R =
alkyl, Q = dianions of 1,2-dioximes, Z = base) are
described. These new and unusual organometallic complexes of cobalt are compared with the alkyl derivs. of vitamin B12 with which they bear a remarkable resemblance. Alkyl-cobaloximes reacted with BF3 etherate forming cyclic oxime boronic esters of composition RCo(Q2Z2F4)Z. Preparation of the first alkylaquocobaloximes,
RCo(Q2H2)H2O, is also reported.
X-ray Crystal Structure Papers for the Coenzyme
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Cyanocobalamin:
- D.C.Hodgkin, J.Kamper, M.Mackay, J.Pickworth, Nature, 1956, 178, 64
- D.C.Hodgkin, Proc. Royal Soc. (London), 1957, A242, 228
- D.C.Hodgkin, Proc. Royal Soc. (London), 1959, A251, 306
- J.G.White, Proc. Royal Soc. (London), 1962, A266, 440
- D.C.Hodgkin, J.Lindsey, M.Mackay, K.N.Trueblood, Proc. Royal Soc. (London), 1962, A242, 475
- D.C.Hodgkin, J.Lindsey, R.A. Sparks, K.N.Trueblood, J.G.White, Proc. Royal Soc. (London), 1962, A242, 494
- C.Brink-Shoemaker, D.W.J.Cruickshank, D.C.Hodgkin, M.J.Kamper, D.Piling, Proc. Royal Soc. (London), 1964, A278, 1
Adenosyl cobalamin:
- P.G.Lenhert and D.C. Hodgkin, Nature, 1961, 192, 937
- P.G. Lenhert, Proc. Royal Soc. (London), 1968, A303, 45
Methyl cobalamin:
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The structure of a B12 coenzyme: methylcobalamin studies by x-ray and NMR
methods. by M. Rossi, J.P.Glusker, L. Randaccio, M.F.Summers, P.J.Toscano, L.G.Marzilli. J. Am. Chem. Soc., 1985, 107(6), 1729-38.
"The structural and NMR studies revealed no particular steric interactions involving the Me group of methylcobalamin. Furthermore, the similarity in structure of the nonalkyl portion of coenzyme B12 and methyl-B12, with a bulky and with a small alkyl ligand, suggested that the bulkiness of the alkyl substituent in coenzyme B12 is not a major structural determinant."
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