Barone, V.: Structure, magnetic properties and reactivities of open-shell
species from density functional and self-consistent hybrid methods, in:
Recent Advances in Density-Functional Methods, edited by: Chong, D. P.,
World Scientific Publishing, Singapore, 287–334, 1996.
Biskup, T., Schleicher, E., Okafuji, A., Link, G., Hitomi, K., Getzoff, E.
D., and Weber, S.: Direct observation of a photoinduced radical pair in a
cryptochrome blue-light photoreceptor, Angew. Chem. Int. Ed., 48, 404–407,
2009.
Bown, D. H., Keller, P. J., Floss, H. G., Sedlmaier, H., and Bacher, A.:
Solution structures of 6,7-dimethyl-8-substituted-lumazines.
13C NMR
evidence for intramolecular ether formation, J. Org. Chem., 51, 2461–2467,
1986.
Breugst, M., Eschenmoser, A., and Houk, K. N.: Theoretical exploration of
the mechanism of riboflavin formation from 6,7-dimethyl-8-ribityllumazine:
nucleophilic catalysis, hydride transfer, hydrogen atom transfer, or
nucleophilic addition?, J. Am. Chem. Soc., 135, 6658–6668, 2013.
Closs, G. L. and Sitzmann, E. V.: Measurements of degenerate radical
ion–neutral molecule electron exchange by microsecond time-resolved CIDNP.
Determination of relative hyperfine coupling constants of radical cations of
chlorophylls and derivatives, J. Am. Chem. Soc., 103, 3217–3219, 1981.
Daniels, B. J., Li, F. F., Furkert, D. P., and Brimble, M. A.: Naturally
occurring lumazines, J. Nat. Prod., 82, 2054–2065, 2019.
Denofrio, M. P., Dántola, M. L., Vicendo, P., Oliveros, E., Thomas, A.
H., and Lorente, C.: Mechanism of electron transfer processes photoinduced
by lumazine, Photochem. Photobiol. Sci., 11, 409–417, 2012.
Ehrenberg, A., Hemmerich, P., Müller, F., and Pfleiderer, W.: Electron
spin resonance of pteridine radicals and the structure of hydropteridines,
Eur. J. Biochem., 16, 584–591, 1970.
Frühwirth, S., Teich, K., and Klug, G.: Effects of the cryptochrome CryB
from
Rhodobacter sphaeroides on global gene expression in the dark or blue light or in the presence of singlet oxygen, PLoS ONE, 7, e33791, https://doi.org/10.1371/journal.pone.0033791, 2012.
Fuchs, M., Schleicher, E., Schnegg, A., Kay, C. W. M., Törring, J. T.,
Bittl, R., Bacher, A., Richter, G., Möbius, K., and Weber, S.: The
g-tensor of the neutral flavin radical cofactor of DNA photolyase revealed
by 360-GHz electron paramagnetic resonance spectroscopy, J. Phys. Chem. B,
106, 8885–8890, 2002.
Geisselbrecht, Y., Frühwirth, S., Schroeder, C., Pierik, A. J., Klug,
G., and Essen, L.-O.: CryB from
Rhodobacter sphaeroides: a unique class of cryptochromes with new
cofactors, EMBO Rep., 13, 223–229, 2012.
Gerhardt, S., Schott, A.-K., Kairies, N., Cushman, M., Illarionov, B.,
Eisenreich, W., Bacher, A., Huber, R., Steinbacher, S., and Fischer, M.:
Studies on the reaction mechanism of riboflavin synthase: X-ray crystal
structure of a complex with 6-carboxyethyl-7-oxo-8-ribityllumazine,
Structure, 10, 1371–1381, 2002.
Goez, M., Mok, K. H., and Hore, P. J.: Photo-CIDNP experiments with an
optimized presaturation pulse train, gated continuous illumination, and a
background-nulling pulse grid, J. Magn. Reson., 177, 236–246, 2005.
Görner, H.: Oxygen uptake after electron transfer from amines, amino
acids and ascorbic acid to triplet flavins in air-saturated aqueous
solution, J. Photochem. Photobiol. B Biol., 87, 73–80, 2007.
Halgren, T. A.: Merck molecular force field. I. Basis, form, scope,
parameterization, and performance of MMFF94, J. Comput. Chem., 17, 490–519,
1996a.
Halgren, T. A.: Merck molecular force field. II. MMFF94 van der Waals and
electrostatic parameters for intermolecular interactions, J. Comput. Chem.,
17, 520–552, 1996b.
Hanwell, M. D., Curtis, D. E., Lonie, D. C., Vandermeersch, T., Zurek, E.,
and Hutchison, G. R.: Avogadro: an advanced semantic chemical editor,
visualization, and analysis platform, J. Cheminformatics, 4, 17, https://doi.org/10.1186/1758-2946-4-17,
2012.
Kaptein, R.: Simple rules for chemically induced dynamic nuclear
polarization, J. Chem. Soc. D, 1971, 732–733, https://doi.org/10.1039/C29710000732, 1971.
Kim, R.-R., Illarionov, B., Joshi, M., Cushman, M., Lee, C. Y., Eisenreich,
W., Fischer, M., and Bacher, A.: Mechanistic insights on riboflavin synthase
inspired by selective binding of the 6,7-dimethyl-8-ribityllumazine
exomethylene anion, J. Am. Chem. Soc., 132, 2983–2990, 2010.
Kirste, B.: DFT calculations of hyperfine coupling constants of organic
π radicals and comparison with empirical equations and experiment, Magn.
Reson. Chem., 54, 835–841, 2016.
Kis, K., Kugelbrey, K., and Bacher, A.: Biosynthesis of riboflavin. The
reaction catalyzed by 6,7-dimethyl-8-ribityllumazine synthase can proceed
without enzymatic catalysis under physiological conditions, J. Org. Chem.,
66, 2555–2559, 2001.
Koka, P. and Lee, J.: Separation and structure of the prosthetic group of
the blue fluorescence protein from the bioluminescent bacterium
Photobacterium phosphoreum, Proc. Natl. Acad. Sci. USA, 76, 3068–3072, 1979.
Kühling, O.: Ueber die Oxydation des Tolualloxazins, Ber. Dtsch. Chem.
Ges., 27, 2116–2119, 1894.
Kühling, O.: Ueber die Oxydation des Tolualloxazins II., Ber. Dtsch.
Chem. Ges., 28, 1968–1971, 1895.
Kuhn, L. T.: Photo-CIDNP NMR spectroscopy of amino acids and proteins, Top.
Curr. Chem., 338, 229–300, 2013.
Masuda, T.: Application of chromatography. XXXI. Structure of a green
fluorescent substance produced by
Eremothecium ashbyii, Pharm. Bull., 5, 28–30, 1957.
McNaught, A. D. and Wilkinson, A.: International Union of Pure and Applied
Chemistry. Compendium of Chemical Terminology. IUPAC Recommendations, 2nd
edn., Blackwell Scientific Publications, Oxford, UK, 1997.
Morozova, O. B., Ivanov, K. L., Kiryutin, A. S., Sagdeev, R. Z.,
Köchling, T., Vieth, H.-M., and Yurkovskaya, A. V.: Time-resolved CIDNP:
an NMR way to determine the EPR parameters of elusive radicals, Phys. Chem.
Chem. Phys., 13, 6619–6627, 2011.
Morozova, O. B., Panov, M. S., Fishman, N. N., and Yurkovskaya, A. V.:
Electron transfer vs. proton-coupled electron transfer as the mechanism of
reaction between amino acids and triplet-excited benzophenones revealed by
time-resolved CIDNP, Phys. Chem. Chem. Phys., 20, 21127–21135, 2018.
Neese, F.: The ORCA program system, Wiley Interdiscip. Rev. Comput. Mol.
Sci., 2, 73–78, 2012.
Neese, F.: Software update: the ORCA program system, version 4.0, Wiley
Interdiscip. Rev. Comput. Mol. Sci., 8, e1327, https://doi.org/10.1002/wcms.1327, 2018.
Oberpichler, I., Pierik, A. J., Wesslowski, J., Pokorny, R., Rosen, R.,
Vugman, M., Zhang, F., Neubauer, O., Ron, E. Z., Batschauer, A., and
Lamparter, T.: A photolyase-like protein from
Agrobacterium tumefaciens with an iron-sulfur cluster,
PLoS ONE, 6, e26775, https://doi.org/10.1371/journal.pone.0026775, 2011.
Okafuji, A., Schnegg, A., Schleicher, E., Möbius, K., and Weber, S.:
G-tensors of the flavin adenine dinucleotide radicals in glucose oxidase: a
comparative multifrequency electron paramagnetic resonance and
electron–nuclear double resonance study, J. Phys. Chem. B, 112, 3568–3574,
2008.
Paulus, B., Illarionov, B., Nohr, D., Roellinger, G., Kacprzak, S., Fischer,
M., Weber, S., Bacher, A., and Schleicher, E.: One protein, two
chromophores: comparative spectroscopic characterization of
6,7-dimethyl-8-ribityllumazine and riboflavin bound to lumazine protein, J.
Phys. Chem. B, 118, 13092–13105, 2014.
Pfleiderer, W., Bunting, J. W., Perrin, D. D., and Nübel, G.: Synthese
und Struktur 8-substituierter Lumazine, Chem. Ber., 99, 3503–3523, 1966.
Plaut, G. W. E.: Studies on the stoichiometry of the enzymic conversion of
6,7-dimethyl-8-ribityllumazine to riboflavin, J. Biol. Chem., 235,
PC41–PC42, 1960.
Plaut, G. W. E.: Studies on the nature of the enzymic conversion of
6,7-dimethyl-8-ribityllumazine to riboflavin, J. Biol. Chem., 238,
2225–2243, 1963.
Pompe, N., Chen, J., Illarionov, B., Panter, S., Fischer, M., Bacher, A.,
and Weber, S.: Methyl groups matter: photo-CIDNP characterizations of the
semiquinone radicals of FMN and demethylated FMN analogs, J. Chem. Phys.,
151, 235103, https://doi.org/10.1063/1.5130557, 2019.
Schmidt, G. H. and Viscontini, M.: 5. Fluoreszierende Stoffe aus Roten
Waldameisen der Gattung
Formica (
Ins.
Hym.). Isolierung von Lumazin-Derivaten aus
Ameisenmännchen, Helv. Chim. Acta, 50, 34–42, 1967.
Schnegg, A., Kay, C. W. M., Schleicher, E., Hitomi, K., Todo, T.,
Möbius, K., and Weber, S.: The g-tensor of the flavin cofactor in (6–4)
photolyase: a 360 GHz/12.8 T electron paramagnetic resonance study, Mol.
Phys., 104, 1627–1633, 2006.
Schreier, W. J., Pugliesi, I., Koller, F. O., Schrader, T. E., Zinth, W.,
Braun, M., Kacprzak, S., Weber, S., Römisch-Margl, W., Bacher, A.,
Illarionov, B., and Fischer, M.: Vibrational spectra of the ground and the
singlet excited
ππ* state of 6,7-dimehtyl-8-ribityllumazine, J.
Phys. Chem. B, 115, 3689–3697, 2011.
Sheppard, D. M. W., Li, J., Henbest, K. B., Neil, S. R. T., Maeda, K.,
Storey, J., Schleicher, E., Biskup, T., Rodriguez, R., Weber, S., Hore, P.
J., Timmel, C. R., and Mackenzie, S. R.: Millitesla magnetic field effects
on the photocycle of an animal cryptochrome, Sci. Rep., 7, 42228, https://doi.org/10.1038/srep42228, 2017.
Small, E. D., Koka, P., and Lee, J.: Lumazine protein from the
bioluminescent bacterium
Photobacterium phosphoreum. Purification and characterization, J. Biol.
Chem., 255, 8804–8810, 1980.
Stephens, P. J., Devlin, F. J., Chabalowski, C. F., and Frisch, M. J.:
Ab initio
calculation of vibrational absorption and circular dichroism spectra using
density functional force fields, J. Phys. Chem., 98, 11623–11627, 1994.
Torres, F., Sobol, A., Greenwald, J., Renn, A., Morozova, O., Yurkovskaya,
A., and Riek, R.: Molecular features toward high photo-CIDNP
hyperpolarization explored through the oxidocyclization of tryptophan, Phys.
Chem. Chem. Phys., 23, 6641–6650, 2021.
Truffault, V., Coles, M., Diercks, T., Abelmann, K., Eberhardt, S.,
Lüttgen, H., Bacher, A., and Kessler, H.: The solution structure of the
N-terminal domain of riboflavin synthase, J. Mol. Biol., 309, 949–960, 2001.
von Zadow, A., Ignatz, E., Pokorny, R., Essen, L.-O., and Klug, G.:
Rhodobacter sphaeroides CryB is a bacterial cryptochrome with (6–4) photolyase activity, FEBS J.,
283, 4291–4309, 2016.
Witwicki, M., Walencik, P. K., and Jezierska, J.: How accurate is density
functional theory in predicting spin density? An insight from the prediction
of hyperfine coupling constants, J. Mol. Model., 26, 10, https://doi.org/10.1007/s00894-019-4268-0, 2020.
Wörner, J., Chen, J., Bacher, A., and Weber, S.: Non-classical disproportionation revealed by photo-CIDNP NMR, FreiDok plus, available at:
https://freidok.uni-freiburg.de/data/194780, last access: 5 May 2021.
Zhang, F., Scheerer, P., Oberpichler, I., Lamparter, T., and Krauß, N.:
Crystal structure of a prokaryotic (6-4) photolyase with an Fe-S cluster and
a 6,7-dimethyl-8-ribityllumazine antenna chromophore, Proc. Natl. Acad. Sci.
USA, 110, 7217–7222, 2013.