Assessing Electronically Excited States of Cobalamins …
257
64. Park K, Brunold TC (2013) Combined spectroscopic and computational analysis of the vibrational properties of vitamin B 12 in its Co 3+ , Co 2+ , and Co 1+ oxidation states. J Phys Chem B
117:5397–5410
65. Peach MJ, Benfield P, Helgaker T, Tozer DJ (2008) Excitation energies in density functional
theory: an evaluation and a diagnostic test. J Chem Phys 128(044):118
66. Perry CB, Marques HM (2005) Probing the cis and trans influrence in cobalamin chemistry by
electronic spectroscopy. S Afr J Chem 58:9–15
67. Pratt JM (1972) Inorganic chemistry of vitamin B 12 . Academic Press, London
68. Pratt JM (1999) Electronic structure and spectra of B 12 : from trans effects to protein conformation I and II. In: Banerjee R (ed) Chemistry and biochemistry of B 12 . Wiley, New York, pp
113–164
69. Ragsdale SW (2006) Metals and their scaffolds to promote difficult enzymatic reactions. Chem
Rev 106:3317–3337
70. Robertson WD, Wang M, Warncke K (2011) Characterization of protein contributions to cobaltcarbon bond cleavage catalysis in adenosylcobalamin-dependent ethanolamine ammonia-lyase
by using photolysis in the ternary complex. J Am Chem Soc 133:6968–77
71. Roman-Melendez GD, von Glehn P, Harvey JN, Mulholland AJ, Marsh ENL (2014) Role
of active site residues in promoting cobalt-carbon bond homolysis in adenosylcobalamindependent mutases revealed through experiment and computation. Biochemistry 53:169–77
72. Ruetz M, Gherasim C, Gruber K, Fedosov S, Banerjee R, Kräutler B (2013) Access to
organometallic arylcobaltcorrins through radical synthesis: 4-ethylphenylcobalamin, a potential “antivitamin B 12 ”. Angew Chem Int Ed 52:2606–2610
73. Ruetz M, Salchner R, Wurst K, Fedosov S, Kräutler B (2013) Phenylethynylcobalamin: a
lightstable and thermolysisresistant organometallic vitamin B 12 derivative prepared by radical
synthesis. Angew Chem Int Ed 52:11,406–11,409
74. Runge E, Gross EKU (1984) Density-functional theory for time-dependent systems. Phys Rev
Lett 52:997–1000
75. Rury AS, Wiley TE, Sension RJ (2015) Energy cascades, excited state dynamics, and photochemistry in cob(III)alamins and ferric porphyrins. Acc Chem Res 48:860–867
76. Ryde U, Mata RA, Grimme S (2011) Does DFT-D estimate accurate energies for the binding
of ligands to metal complexes? Datlon Trans 40:11,176–11,183
77. Sandala GM, Smith DM, Radom L (2010) Modeling the reactions catalyzed by coenzyme
B 12 -dependent enzymes. Acc Chem Res 43:642–651
78. Sension RJ, Harris DA, Cole AG (2005a) Time-resolved spectroscopic studies of B 12 coenzymes: Comparison of the influence of solvent on the primary photolysis mechanism and
geminate recombination of methyl-, ethyl-, n-propyl, and 5’-deoxyadenosylcobalamin. J Phys
Chem B 109:21,954–21,962
79. Sension RJ, Harris DA, Stickrath A, Cole AG, Fox CC, Marsh EN (2005b) Time-resolved
measurements of the photolysis and recombination of adenosylcobalamin bound to glutamate
mutase. J Phys Chem B 109:18,146–18,152
80. Shell TA, Lawrence DS (2015) Vitamin B 12 : a tunable, long wavelength, light-responsive
platform for launching therapeutic agents. Acc Chem Res 48:2866–2874
81. Shell TA, Shell JR, Rodgers ZL, Lawrence DS (2014) Tunable visible and near-IR photoactivation of light-responsive compounds by using fluorophores as light-capturing antennas. Angew
Chem Int Ed 53:875–878
82. Shiang JJ, Walker LA, Anderson NA, Cole AG, Sension RJ (1999) Time-resolved spectroscopic
studies of B 12 coenzymes: The photolysis of methylcobalamin is wavelength dependent. J Phys
Chem B 103:10,532–10,539
83. Shiang JJ, Cole AG, Sension RJ, Hang K, Weng Y, Trommel JS, Marzilli LG, Lian T (2006)
Ultrafast excited-state dynamics in vitamin B 12 and related cob(III)alamins. J Am Chem Soc
128:801–808
84. Solheim H, Kornobis K, Ruud K, Kozlowski PM (2011) Electronically excited states of vitamin
B 12 and methylcobalamin: theoretical analysis of absorption, CD, and MCD data. J Phys Chem
B 115:737–748
257
64. Park K, Brunold TC (2013) Combined spectroscopic and computational analysis of the vibrational properties of vitamin B 12 in its Co 3+ , Co 2+ , and Co 1+ oxidation states. J Phys Chem B
117:5397–5410
65. Peach MJ, Benfield P, Helgaker T, Tozer DJ (2008) Excitation energies in density functional
theory: an evaluation and a diagnostic test. J Chem Phys 128(044):118
66. Perry CB, Marques HM (2005) Probing the cis and trans influrence in cobalamin chemistry by
electronic spectroscopy. S Afr J Chem 58:9–15
67. Pratt JM (1972) Inorganic chemistry of vitamin B 12 . Academic Press, London
68. Pratt JM (1999) Electronic structure and spectra of B 12 : from trans effects to protein conformation I and II. In: Banerjee R (ed) Chemistry and biochemistry of B 12 . Wiley, New York, pp
113–164
69. Ragsdale SW (2006) Metals and their scaffolds to promote difficult enzymatic reactions. Chem
Rev 106:3317–3337
70. Robertson WD, Wang M, Warncke K (2011) Characterization of protein contributions to cobaltcarbon bond cleavage catalysis in adenosylcobalamin-dependent ethanolamine ammonia-lyase
by using photolysis in the ternary complex. J Am Chem Soc 133:6968–77
71. Roman-Melendez GD, von Glehn P, Harvey JN, Mulholland AJ, Marsh ENL (2014) Role
of active site residues in promoting cobalt-carbon bond homolysis in adenosylcobalamindependent mutases revealed through experiment and computation. Biochemistry 53:169–77
72. Ruetz M, Gherasim C, Gruber K, Fedosov S, Banerjee R, Kräutler B (2013) Access to
organometallic arylcobaltcorrins through radical synthesis: 4-ethylphenylcobalamin, a potential “antivitamin B 12 ”. Angew Chem Int Ed 52:2606–2610
73. Ruetz M, Salchner R, Wurst K, Fedosov S, Kräutler B (2013) Phenylethynylcobalamin: a
lightstable and thermolysisresistant organometallic vitamin B 12 derivative prepared by radical
synthesis. Angew Chem Int Ed 52:11,406–11,409
74. Runge E, Gross EKU (1984) Density-functional theory for time-dependent systems. Phys Rev
Lett 52:997–1000
75. Rury AS, Wiley TE, Sension RJ (2015) Energy cascades, excited state dynamics, and photochemistry in cob(III)alamins and ferric porphyrins. Acc Chem Res 48:860–867
76. Ryde U, Mata RA, Grimme S (2011) Does DFT-D estimate accurate energies for the binding
of ligands to metal complexes? Datlon Trans 40:11,176–11,183
77. Sandala GM, Smith DM, Radom L (2010) Modeling the reactions catalyzed by coenzyme
B 12 -dependent enzymes. Acc Chem Res 43:642–651
78. Sension RJ, Harris DA, Cole AG (2005a) Time-resolved spectroscopic studies of B 12 coenzymes: Comparison of the influence of solvent on the primary photolysis mechanism and
geminate recombination of methyl-, ethyl-, n-propyl, and 5’-deoxyadenosylcobalamin. J Phys
Chem B 109:21,954–21,962
79. Sension RJ, Harris DA, Stickrath A, Cole AG, Fox CC, Marsh EN (2005b) Time-resolved
measurements of the photolysis and recombination of adenosylcobalamin bound to glutamate
mutase. J Phys Chem B 109:18,146–18,152
80. Shell TA, Lawrence DS (2015) Vitamin B 12 : a tunable, long wavelength, light-responsive
platform for launching therapeutic agents. Acc Chem Res 48:2866–2874
81. Shell TA, Shell JR, Rodgers ZL, Lawrence DS (2014) Tunable visible and near-IR photoactivation of light-responsive compounds by using fluorophores as light-capturing antennas. Angew
Chem Int Ed 53:875–878
82. Shiang JJ, Walker LA, Anderson NA, Cole AG, Sension RJ (1999) Time-resolved spectroscopic
studies of B 12 coenzymes: The photolysis of methylcobalamin is wavelength dependent. J Phys
Chem B 103:10,532–10,539
83. Shiang JJ, Cole AG, Sension RJ, Hang K, Weng Y, Trommel JS, Marzilli LG, Lian T (2006)
Ultrafast excited-state dynamics in vitamin B 12 and related cob(III)alamins. J Am Chem Soc
128:801–808
84. Solheim H, Kornobis K, Ruud K, Kozlowski PM (2011) Electronically excited states of vitamin
B 12 and methylcobalamin: theoretical analysis of absorption, CD, and MCD data. J Phys Chem
B 115:737–748