- Stabler , S.P. 1999 . B12 and nutrition. In Chemistry and Biochemistry of B11 , Edited by: Banerjee , R. 343 – 365 . New York : Wiley .
- Hogenkamp , H.P.C. 1999 . B12: 1948-1998. In Chemistry and Biochemistry of B11 , Edited by: Banerjee , R. 3 – 8 . New York : Wiley .
- Hodgkin , D.C. , Kamper , J. , Mackay , M. , Pickworth , J. , Tmeblood , K.N. and White , J.G. 1956 . Structure of vitamin B12 . Nature (London} , 178 : 64 – 66 .
- Lenhert , P.C. and Hodgkin , D.C. 1961 . Structure of the 5,6-dimethylbenzimidazolylcobamide coenzyme . Nature (London} , 192 : 937 – 938 .
- Rossi , M. , Glusker , J.P. , Randaccio , L. , Summers , M.F. , Toscano , PJ. and Marzilli , L.G. 1985 . The structure of a B12 coenzyme: Methylcobalamin studies by X-ray and NMR methods . J. Am. Chem. Soc. , 107 : 1729 – 1738 .
- Kovacs , I.A. , Shoner , S.C. and Ellison , I.J. 1995 . Metal-carbon bonds in nature . Science , 270 : 587 – 588 .
- Kumar , M. , Qiu , D. , Spiro , T.G. and Ragsdale , S.W. 1995 . A methylnickel intermediate in a bimetallic mechanism of acetyl-coenzyme A synthesis by anaerobic bacteria . Science , 270 : 628 – 630 .
- Drennan , C.L. , Huang , S. , Drummond , J.T. , Matthews , R.G. and Ludwig , M.L. 1994 . How a protein binds B12: A 3.0 Å X-ray structure of B12-binding domains of methionine synthase . Science , 266 : 1669 – 1674 .
- Mancia , F. , Keep , N.H. , Nakagawa , A. , Leadlay , P.F. , McSweeney , S. , Rasmussen , B. , Bösecke , P. , Dial , O. and Evans , P.R. 1996 . How coenzyme B12 radicals are generated: The crystal structure of methylmalonyl-coenzyme A mutase at 2 Å resolution . Structure , 4 : 339 – 350 .
- Mancia , F. and Evans , P.R. 1998 . Conformational changes on substrate binding to methylmalonyl-CoA mutase and new insights into the free radical mechanism . Structure , 6 : 711 – 720 .
- Mancia , F. , Smith , G.A. and Evans , P.R. 1999 . Crystal structure of substrate complexes of methylmalonyl-CoA mutase . Biochemistry , 38 : 7999 – 8005 .
- Reitzer , R. , Gruber , JC , Jogi , G. , Wagner , U.G. , Bothe , H. , Buckel , W. and Kratky , C. 1999 . Glutamate mutase from Clostridiium cochlearium: The structure of a coenzyme B12-dependent enzyme provides new mechanistic insights . Structure , 7 : 891 – 902 .
- Gruber , K. , Reitzer , R. and Kratky , C. 2001 . Radical shuttling in a protein: Ribose pseudorotation controls alkyl-radical transfer in the coenzyme B12 dependent enzyme glutamate mutase . Angew. Chem. Int. Ed. , 40 : 3377 – 3380 .
- Shibata , N. , Masuda , J. , Tobimatsu , T. , Toraya , T. , Suto , K. , Morimoto , Y. and Yasuoka , N. 1999 . A new mode of B12 binding and the direct participation of a potassium ion in enzyme catalysis: X-ray structure of diol dehydratase . Structure , 7 : 997 – 1008 .
- Toraya , T. 2000 . The structure and the mechanism of action of coenzyme B12-dependent diol dehydratases . J. MoI. Catal. , B10 : 87 – 106 .
- Brown , K.L. and Marques , H.M. 2001 . Molecular modeling of the mechanochemical triggering mechanism for catalysis of carbon-cobalt bond homolysis in coenzyme B|2 . J. Inorg. Biochem. , 83 : 121 – 132 .
- Matthews , R.G. 2001 . Cobalamin-dependent methyltransferases . Ace. Chem. Res. , 34 : 681 – 689 .
- Chowdhury , S. and Banerjee , R. 2000 . Thermodynamic and kinetic characterization of Co-C bond homolysis catalyzed by coenzyme B12-dependent methylmalonyl-CoA mutase . Biochemistry , 39 : 7998 – 8006 .
- Randaccio , L. , Pahor , N.B. , Zangrando , E. and Marzilli , L.G. 1989 . Structural properties of organocobalt coenzyme B12 models . Chem. Soc. Rev. , 18 : 225 – 250 .
- Glusker , J.P. 1982 . X-ray crystallography of Bi2 and cobaloximes , Edited by: Dolphin , D. vol. 1 , B12 23 – 106 . New York : Wiley .
- Pett , V.B. , Liebman , M.N. , Murray-Rust , P. , Prasad , K. and Glusker , J.P. 1987 . Conformational variability of corrins: Some methods of analysis . J. Am. Chem. Soc. , 109 : 3207 – 3215 .
- Gruber , K. , Jogi , G. , Klinischer , G. and Kratky , C. 1988 . “ High-resolution crystal structures of cobalamins ” . In Vitamin B12 and B12-Proteins , Edited by: Kräutler , B. , Arigoni , D. and Golding , B.T. 335 – 347 . New York : Wiley .
- Geno , M.K. and Halpern , J. 1987 . Why does nature not use the porphyrin ligand in vitamin Bi2? . J. Am. Chem. Soc. , 109 : 1238 – 1240 .
- Halpern , J. 1988 . Organometallic chemistry in biology: The role of vitamin Bi2 . Bull. Soc. Chim. Fr. no. , 2 : 187 – 191 .
- Savage , H.F.J. , Lindley , P.F. , Finney , J.L. and Timmins , P.A. 1987 . High-resolution neutron and X-ray refinement of vitamin B12 coenzyme, C72H1ooCoN12O17P.17H2O . Ada Cryst. , B43 : 280 – 295 .
- Bouquiere , J.P. , Finney , J.L. , Lehmann , M.S. , Lindley , P.F. and Savage , H.F.J. 1993 . Highresolution neutron study of vitamin B12 coenzyme at 15 K . Acta Cryst. , B49 : 79 – 89 .
- Kratky , C. and Kräutler , B. 1999 . “ X-ray crystallography of B12 ” . In Chemistry and Biochemistry of B12 , Edited by: Banerjee , R. 9 – 41 . New York : Wiley .
- Pratt , I.M. 1999 . “ The roles of Co, corrin, and protein. I. Co-ligand bonding and the Irans effect ” . In Chemistry and Biochemistry of B12 , Edited by: Banerjee , R. 73 – 112 . New York : Wiley .
- Pratt , J.M. 1999 . “ The roles of Co, corrin, and protein. II. Electronic spectra and structure of the corrin ligand: Molecular machinery of the protein ” . In Chemistry and Biochemistry of B12 , Edited by: Banerjee , R. 113 – 164 . New York : Wiley .
- Choo , P.L. , Mulichak , A.M. , Jones , R.W. Jr. , Bacon , J.W. , Pett , V.B. and Zacharias , D.E. 1990 . A new type of organocobalt complex with a buckled equatorial ligand . Inorg. Chim. Acta. , 171 : 183 – 192 .
- McFarland , C.A. , Gross , S.A. , Winfield , J.S. and Pett , V.B. 1994 . An ethyl-cobalt complex with a buckled equatorial ligand . Inorg. Chim. Acta. , 221 : 35 – 40 .
- Jaynes , B.S. , Ren , T. , Masschelein , A. and Lippard , S.J. 1993 . Stereochemical control of reactivity in Co(III} alkyl complexes of the tropocoronand ligand system . J. Am. Chem. Soc. , 115 : 5589 – 5599 .
- Fischer , A. and Pett , V.B. Coenzyme B12: Finding the smoking gun . American Crystallographic Association Annual Meeting . Los Angeles. presentation 02.01.09.
- Pett , V.B. , Fischer , A.E. , Dudley , G.K. and Majors , S.O. To be submitted for publication , Cambridge Crystallographic Data Centre deposition number 189472
- Finke , R.G. and Schiraldi , D.A. 1983 . Model studies of coenzyme B12 dependent diol dehydratase. 2. A kinetic and mechanistic study focusing upon the cobalt participation or nonparticipation question . J. Am. Chem. Soc. , 105 : 7605 – 7617 .
- Elliott , C.M. , Hershenhart , E. , Finke , R.G. and Smith , B.L. 1981 . Coenzyme B12 model studies: An electrochemical comparison of cobaloxime and Co[C2(DO}(DOH}Pn] complexes to coenzyme B12 . J. Am. Chem. Soc. , 103 : 5558 – 5566 .
- Marsh , E.N.G. and Drennan , C.L. 2001 . Adenosylcobalamin-dependent isomerases: New insights into structure and mechanism . Curr. Opinion Chem. Biol. , 5 : 499 – 505 .
- Toscano , PJ. and Marzilli , L.G. 1979 . An extensive trans-effect series: The reaction of coordinated trimethyl phosphite . Inorg. Chem. , 18 : 421 – 424 .
- Appleton , T.G. , Clark , H.C. and Manzer , L.E. 1973 . The tram-influence: Its measurement and significance . Coord. Chem. Rev. , 10 : 335 – 422 .
- Stewart , J.J.P. 1989 . Optimization of parameters for semiempirical methods. I. Method . J. Computat. Chem. , 10 : 209 – 220 .
- Stewart , J.J.P. 1989 . Optimization of parameters for semiempirical methods. D. Applications . J. Computat. Chem. , 10 : 221 – 264 .
- Hehre , W.J. , Yu , J. , Klunzinger , P.E. and Lou , L. 1998 . A Brief Guide to Molecular Mechanics and Quantum Chemical Calculations , Irvine, CA : Wavefunction .
- Costa , G. and Mestroni , G. 1967 . Tetrahedron Lett , 41 : 4005
- Costa , G. , Mestroni , G. and Savorgnani , E. de . 1969 . Inorg. Chim. Acta. , 3 : 323
- Dong , S. , Padmakumar , R. , Banerjee , R. and Spiro , T.G. 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 .
- Dong , S. , Padmakumar , R. , Banerjee , R. and Spiro , T.G. 1998 . Co-C force constants from resonance Raman spectra of alkylcobalamins: Insensitivity to dimethylbenzimidazole coordination . Inorg. Chim. Acta. , 270 : 392 – 398 .
- Sirovatka , J.M. and Finke , R.G. 1999 . Coenzyme B12 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 s and p effects . Inorg. Chem. , 38 : 1697 – 1707 .
- Sirovatka , J.M. , Rappe , A.K. and Finke , R.G. 2000 . Molecular mechanics studies of coenzyme B12 complexes with constrained Co-N(axial-base} bond lengths: Introduction of the universal force field (UFF} to coenzyme B12 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 .
- Dölker , N. , Maseras , F. and Liedos , A. 2001 . A density function study on the effect of the Irans axial ligand of cobalamin on the homolytic cleavage of the Co-C bond . J. Phys. Chem. , B105 : 7564 – 7571 .
- Jensen , K.P. , Sauer , S.P.A. , Liljefors , T. and Norrby , P.-O. 2001 . Theoretical investigation of steric and electronic effects in coenzyme B12 models . Organometallics , 20 : 550 – 556 .
- Jensen , K.P. and Ryde , U. 2002 . The axial N-base has minor influence on Co-C bond cleavage in cobalamins . J. MoI. Struct. (Theochem} , 585 : 239 – 255 .
Probing the Mechanism of Coenzyme B 12 : Synthesis, Crystal Structures, and Molecular Modeling of Coenzyme B 12 Model Compounds
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