256
M. J. Toda et al.
44. Kumar M, Kozlowski PM (2017) Electronic and structural properties of cob(I)alamin: ramifications for B 12 -dependent processes. Coord Chem Rev 333:71–81
45. Kuta J, Patchkovskii S, Zgierski MZ, Kozlowski PM (2006) Performance of DFT in modeling
electronic and structural properties of cobalamins. J Comput Chem 27:1429–1437
46. Kuta J, Wuerges J, Randaccio L, Kozlowski PM (2009) Axial bonding in alkylcobalamins:
DFT analysis of the inverse versus normal trans influence. J Phys Chem A 113:11,604–11,612
47. Kutta RJ, Hardman SJ, Johannissen LO, Bellina B, Messiha HL, Ortiz-Guerrero JM, EliasArnanz M, Padmanabhan S, Barran P, Scrutton NS, Jones AR (2015) The photochemical
mechanism of a B 12 -dependent photoreceptor protein. Nat Commun 6:7907
48. Lewis NJ, Pfaltz A, Eschenmoser A (1983) Acid-catalyzed demetalation of nickelhydrocorphin and cobalt-corrin complexes with 1,3-propoanedithiol. Angew Chem Int Ed
22:735–736
49. Liptak MD, Brunold TC (2006) Spectroscopic and computational studies of Co 1+ cobalamin: spectral and electronic properties of the “superreduced” B 12 cofactor. J Am Chem Soc
128:9144–9156
50. Liu H, Kornobis K, Lodowski P, Jaworska M, Kozlowski PM (2014) TD-DFT insight into
photodissociation of the Co-C bond in coenzyme B 12 . Front Chem 1:1–12
51. Lodowski P, Jaworska M, Andruniów T, Kumar M, Kozlowski PM (2009) Photodissociation
of Co-C bond in methyl- and methylcobalamin: an insight from TD-DFT calculations. J Phys
Chem B 113:6898–6909
52. Lodowski P, Jaworska M, Kornobis K, Andruniów T, Kozlowski PM (2011) Electronic and
structural properties of low-lying excited states of vitamin B 12 . J Phys Chem B 115:13,304–
13,319
53. Lodowski P, Jaworska M, Andruniów T, Garabato BD, Kozlowski PM (2014) Mechanism of the
S 1 excited state internal conversion in vitamin B 12 . Phys Chem Chem Phys 16:18,675–18,679
54. Lodowski P, Ciura K, Toda MJ, Jaworska M, Kozlowski PM (2017) Photodissociation of
ethylphenylcobalamin antivitamin B 12 . Phys Chem Chem Phys 19:30,310–30,315
55. Luo LB, Li G, Chen HL, Fu SW, Zhang SY (1998) Laser-induced photoacoustic calorimetric
determination of enthalpy and volume changes in photolysis of 5’-deoxyadenosylcobalamin
and methylcobalamin. J Chem Soc Dalton Trans pp 2103–2107
56. Mamun AA, Toda MJ, Lodowski P, Jaworska M, Kozlowski PM (2018) Mechanism of light
induced radical pair formation in coenzyme B 12 -dependent ethanolamine ammonia-lyase. ACS
Catalysis 8:7164–7178
57. Marsh EN, Melendez GD (2012) Adenosylcobalamin enzymes: theory and experiment begin
to converge. Biochim Biophys Acta 1824:1154–1164
58. Martin BD, Finke RG (1990) Co-C homolysis and bond-dissociation energy studies of biological alkylcobalamins: methylcobalamin, including a ≥10 15 Co-CH 3 homolysis rate enhancement at 25 ◦ c following one-electron reduction. J Am Chem Soc 112:2419–2420
59. Martin BD, Finke RG (1992) Methylcobalamins full-strength vs half-strenght cobalt-carbon
sigma-bonds and bond-dissociation enthalpies ≥10 15 Co-CH 3 homolysis rate enhancement
following one-antibonding-electron reduction of methylcobalamin. J Am Chem Soc 114:585–
592
60. Miller NA, Wiley TE, Spears KG, Ruetz M, Kieninger C, Krautler B, Sension RJ (2016) Toward
the design of photoresponsive conditional antivitamins B 12 : a transient absorption study of an
arylcobalamin and an alkynylcobalamin. J Am Chem Soc 138:14,250–14,256
61. Miller NA, Deb A, Alonso-Mori R, Garabato BD, Glownia JM, Kiefer LM, Koralek J, Sikorski
M, Spears KG, Wiley TE, Zhu D, Kozlowski PM, Kubarych KJ, Penner-Hahn JE, Sension RJ
(2017) Polarized XANES monitors femtosecond structural evolution of photoexcited vitamin
B 12 . J Am Chem Soc 139:1894–1899
62. Mutti E, Ruetz M, Birn H, Krütler B, Nexo E (2013) 4-ethylphenyl-cobalamin impairs tissue
uptake of vitamin B 12 and causes vitamin B 12 deficiency in mice. PLOS ONE 8(e75):312
63. Offenhartz PO, Offenhartz BH, Fung MM (1970) Theoretical analysis of corrin optical spectra.
J Am Chem Soc 92:2966–2973
M. J. Toda et al.
44. Kumar M, Kozlowski PM (2017) Electronic and structural properties of cob(I)alamin: ramifications for B 12 -dependent processes. Coord Chem Rev 333:71–81
45. Kuta J, Patchkovskii S, Zgierski MZ, Kozlowski PM (2006) Performance of DFT in modeling
electronic and structural properties of cobalamins. J Comput Chem 27:1429–1437
46. Kuta J, Wuerges J, Randaccio L, Kozlowski PM (2009) Axial bonding in alkylcobalamins:
DFT analysis of the inverse versus normal trans influence. J Phys Chem A 113:11,604–11,612
47. Kutta RJ, Hardman SJ, Johannissen LO, Bellina B, Messiha HL, Ortiz-Guerrero JM, EliasArnanz M, Padmanabhan S, Barran P, Scrutton NS, Jones AR (2015) The photochemical
mechanism of a B 12 -dependent photoreceptor protein. Nat Commun 6:7907
48. Lewis NJ, Pfaltz A, Eschenmoser A (1983) Acid-catalyzed demetalation of nickelhydrocorphin and cobalt-corrin complexes with 1,3-propoanedithiol. Angew Chem Int Ed
22:735–736
49. Liptak MD, Brunold TC (2006) Spectroscopic and computational studies of Co 1+ cobalamin: spectral and electronic properties of the “superreduced” B 12 cofactor. J Am Chem Soc
128:9144–9156
50. Liu H, Kornobis K, Lodowski P, Jaworska M, Kozlowski PM (2014) TD-DFT insight into
photodissociation of the Co-C bond in coenzyme B 12 . Front Chem 1:1–12
51. Lodowski P, Jaworska M, Andruniów T, Kumar M, Kozlowski PM (2009) Photodissociation
of Co-C bond in methyl- and methylcobalamin: an insight from TD-DFT calculations. J Phys
Chem B 113:6898–6909
52. Lodowski P, Jaworska M, Kornobis K, Andruniów T, Kozlowski PM (2011) Electronic and
structural properties of low-lying excited states of vitamin B 12 . J Phys Chem B 115:13,304–
13,319
53. Lodowski P, Jaworska M, Andruniów T, Garabato BD, Kozlowski PM (2014) Mechanism of the
S 1 excited state internal conversion in vitamin B 12 . Phys Chem Chem Phys 16:18,675–18,679
54. Lodowski P, Ciura K, Toda MJ, Jaworska M, Kozlowski PM (2017) Photodissociation of
ethylphenylcobalamin antivitamin B 12 . Phys Chem Chem Phys 19:30,310–30,315
55. Luo LB, Li G, Chen HL, Fu SW, Zhang SY (1998) Laser-induced photoacoustic calorimetric
determination of enthalpy and volume changes in photolysis of 5’-deoxyadenosylcobalamin
and methylcobalamin. J Chem Soc Dalton Trans pp 2103–2107
56. Mamun AA, Toda MJ, Lodowski P, Jaworska M, Kozlowski PM (2018) Mechanism of light
induced radical pair formation in coenzyme B 12 -dependent ethanolamine ammonia-lyase. ACS
Catalysis 8:7164–7178
57. Marsh EN, Melendez GD (2012) Adenosylcobalamin enzymes: theory and experiment begin
to converge. Biochim Biophys Acta 1824:1154–1164
58. Martin BD, Finke RG (1990) Co-C homolysis and bond-dissociation energy studies of biological alkylcobalamins: methylcobalamin, including a ≥10 15 Co-CH 3 homolysis rate enhancement at 25 ◦ c following one-electron reduction. J Am Chem Soc 112:2419–2420
59. Martin BD, Finke RG (1992) Methylcobalamins full-strength vs half-strenght cobalt-carbon
sigma-bonds and bond-dissociation enthalpies ≥10 15 Co-CH 3 homolysis rate enhancement
following one-antibonding-electron reduction of methylcobalamin. J Am Chem Soc 114:585–
592
60. Miller NA, Wiley TE, Spears KG, Ruetz M, Kieninger C, Krautler B, Sension RJ (2016) Toward
the design of photoresponsive conditional antivitamins B 12 : a transient absorption study of an
arylcobalamin and an alkynylcobalamin. J Am Chem Soc 138:14,250–14,256
61. Miller NA, Deb A, Alonso-Mori R, Garabato BD, Glownia JM, Kiefer LM, Koralek J, Sikorski
M, Spears KG, Wiley TE, Zhu D, Kozlowski PM, Kubarych KJ, Penner-Hahn JE, Sension RJ
(2017) Polarized XANES monitors femtosecond structural evolution of photoexcited vitamin
B 12 . J Am Chem Soc 139:1894–1899
62. Mutti E, Ruetz M, Birn H, Krütler B, Nexo E (2013) 4-ethylphenyl-cobalamin impairs tissue
uptake of vitamin B 12 and causes vitamin B 12 deficiency in mice. PLOS ONE 8(e75):312
63. Offenhartz PO, Offenhartz BH, Fung MM (1970) Theoretical analysis of corrin optical spectra.
J Am Chem Soc 92:2966–2973