-
2
-
-
33845312859
-
-
note
-
Abbreviations: CP, cross-polarization; dBF, dibenzyl flavin; DFT, density functional theory; FAD, flavin adenine dinucleotide; FMN, flavin mononucleotide; GIAO, gauge-including atomic orbital; HOMO, highest occupied molecular orbital, used somewhat loosely here to include the several such orbitals that define the reactivity; LUMO, lowest unoccupied molecular orbital, used somewhat loosely to include the several lowest-lying orbitals that define the reactivity; MAS, magic angle spinning; NMR, nuclear magnetic resonance: PASS, phase adjusted spinning sideband; rmsd, root-mean-square deviation; SS, solid state; TARF, tetraacetyl riboflavin.
-
-
-
-
3
-
-
0029038909
-
-
Massey, V. FASEB J. 1995, 9, 473-475.
-
(1995)
FASEB J.
, vol.9
, pp. 473-475
-
-
Massey, V.1
-
5
-
-
0034639898
-
-
Cuello, A. O.; McIntosh, C. M.; Rotello, V. M. J. Am. Chem. Soc. 2000, 122, 3517-3521.
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 3517-3521
-
-
Cuello, A.O.1
McIntosh, C.M.2
Rotello, V.M.3
-
6
-
-
0035923397
-
-
Yin, Y.; Sampson, N. S.; Vrielink, A.; Lario, P. I. Biochemistry 2001, 40, 13779-13787.
-
(2001)
Biochemistry
, vol.40
, pp. 13779-13787
-
-
Yin, Y.1
Sampson, N.S.2
Vrielink, A.3
Lario, P.I.4
-
9
-
-
0037147771
-
-
Guo, F.; Chang, B. H.; Rizzo, C. J. Bioorg. Med. Chem. Lett. 2002, 12, 151-154.
-
(2002)
Bioorg. Med. Chem. Lett.
, vol.12
, pp. 151-154
-
-
Guo, F.1
Chang, B.H.2
Rizzo, C.J.3
-
10
-
-
0026672465
-
-
Akiyama, T.; Simeno, F.; Murakami, M.; Yoneda, F. J. Am. Chem. Soc. 1992, 114, 6613-6620.
-
(1992)
J. Am. Chem. Soc.
, vol.114
, pp. 6613-6620
-
-
Akiyama, T.1
Simeno, F.2
Murakami, M.3
Yoneda, F.4
-
11
-
-
0035827531
-
-
Talfournier, F.; Munro, A. W.; Basran, J.; Sutcliffe, M. J.; Daff, S.; Chapman, S. K.; Scrutton, N. S. J. Biol. Chem. 2001, 276 (23), 20190-20196.
-
(2001)
J. Biol. Chem.
, vol.276
, Issue.23
, pp. 20190-20196
-
-
Talfournier, F.1
Munro, A.W.2
Basran, J.3
Sutcliffe, M.J.4
Daff, S.5
Chapman, S.K.6
Scrutton, N.S.7
-
12
-
-
0031024423
-
-
Ludwig, M. L.; Pattridge, K. A.; Metzger, A. L.; Dixon, M. M.; Eren, M.; Feng, Y.; Swenson, R. P. Biochemists 1997, 36, 1259-1280.
-
(1997)
Biochemists
, vol.36
, pp. 1259-1280
-
-
Ludwig, M.L.1
Pattridge, K.A.2
Metzger, A.L.3
Dixon, M.M.4
Eren, M.5
Feng, Y.6
Swenson, R.P.7
-
13
-
-
0022837145
-
-
Nishimoto, K.; Fukunaga, H.; Yagi, K. J. Biochem. (Tokyo) 1986, 100, 1647-1653.
-
(1986)
J. Biochem. (Tokyo)
, vol.100
, pp. 1647-1653
-
-
Nishimoto, K.1
Fukunaga, H.2
Yagi, K.3
-
14
-
-
8844231392
-
-
Chapman, S., Perham, R., Scrutton, N. S., Eds.; Rudolf Weber: University of Cambridge, UK
-
Yalloway, G. N.; Löhr, F.; Rüterjans, H. In Flavins and Flavoproteins; Chapman, S., Perham, R., Scrutton, N. S., Eds.; Rudolf Weber: University of Cambridge, UK, 2002; pp 679-684.
-
(2002)
Flavins and Flavoproteins
, pp. 679-684
-
-
Yalloway, G.N.1
Löhr, F.2
Rüterjans, H.3
-
15
-
-
0000275732
-
-
Hasford, J. J.; Kemnitzer, W.; Rizzo, C. J. J. Org. Chem. 1997, 62 (16), 5244-5245.
-
(1997)
J. Org. Chem.
, vol.62
, Issue.16
, pp. 5244-5245
-
-
Hasford, J.J.1
Kemnitzer, W.2
Rizzo, C.J.3
-
19
-
-
0015297499
-
-
Müller, F.; Walker, W. H.; Massey, V.; Brustlei, M.; Hemmerich, P. Eur. J. Biochem. 1972, 25 (3), 573.
-
(1972)
Eur. J. Biochem.
, vol.25
, Issue.3
, pp. 573
-
-
Müller, F.1
Walker, W.H.2
Massey, V.3
Brustlei, M.4
Hemmerich, P.5
-
20
-
-
0018787423
-
-
Massey, V.; Ghisla, S.; Moore, E. G. J. Biol. Chem. 1979, 254 (19), 9640-9650.
-
(1979)
J. Biol. Chem.
, vol.254
, Issue.19
, pp. 9640-9650
-
-
Massey, V.1
Ghisla, S.2
Moore, E.G.3
-
21
-
-
2942596455
-
-
Sikorska, E.; Khmelinskii, I.; Koput, J.; Bourdelande, J. L.; Sikorski, M. J. Mol. Str. 2004, 697 (1-3), 137-141.
-
(2004)
J. Mol. Str.
, vol.697
, Issue.1-3
, pp. 137-141
-
-
Sikorska, E.1
Khmelinskii, I.2
Koput, J.3
Bourdelande, J.L.4
Sikorski, M.5
-
23
-
-
0345356187
-
-
Schelvis, J. P. M.; Ramsey, M.; Sokolova, O.; Tavares, C.; Cecala, C.; Connell, K.,; Wagner, S.; Gindt, Y. M. J. Phys. Chem. B 2003, 107 (44), 12352-12362.
-
(2003)
J. Phys. Chem. B
, vol.107
, Issue.44
, pp. 12352-12362
-
-
Schelvis, J.P.M.1
Ramsey, M.2
Sokolova, O.3
Tavares, C.4
Cecala, C.5
Connell, K.6
Wagner, S.7
Gindt, Y.M.8
-
24
-
-
0345733997
-
-
Wille, G.; Ritter, M.; Friedemann, R.; Mantele, W.; Hubner, G. Biochemistry 2003, 42 (50), 14814-14821.
-
(2003)
Biochemistry
, vol.42
, Issue.50
, pp. 14814-14821
-
-
Wille, G.1
Ritter, M.2
Friedemann, R.3
Mantele, W.4
Hubner, G.5
-
25
-
-
3142656596
-
-
Zheng, Y. G.; Carey, P. R.; Palfey, B. A. H. Raman Spec. 2005, 35 (7), 521-525.
-
(2005)
H. Raman Spec.
, vol.35
, Issue.7
, pp. 521-525
-
-
Zheng, Y.G.1
Carey, P.R.2
Palfey, B.A.3
-
26
-
-
0034829412
-
-
Weber, S.; Möbius, K.; Richter, G.; Kay, C. W. M. J. Am. Chem. Soc. 2001, 123, 3790-3798.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 3790-3798
-
-
Weber, S.1
Möbius, K.2
Richter, G.3
Kay, C.W.M.4
-
27
-
-
0000791239
-
-
Müller, F., Ed.; CRC: Boca Raton FL
-
Müller, F. In Chemistry and Biochemistry of Flavoenzymes; Müller, F., Ed.; CRC: Boca Raton FL, 1992; Vol. III, pp 558-595.
-
(1992)
Chemistry and Biochemistry of Flavoenzymes
, vol.3
, pp. 558-595
-
-
Müller, F.1
-
28
-
-
2142642259
-
-
Eisenreich, W.; Kemter, K.; Bacher, A.; Mulrooney, S. B.; Williams, C. h.; Müller, F. Eur. J. Biochem. 2004, 271 (8), 1437-1452.
-
(2004)
Eur. J. Biochem.
, vol.271
, Issue.8
, pp. 1437-1452
-
-
Eisenreich, W.1
Kemter, K.2
Bacher, A.3
Mulrooney, S.B.4
Williams, C.H.5
Müller, F.6
-
29
-
-
0021759003
-
-
Moonen, C. T. W.; Vervoort, J.; Müller, F. Biochemistry 1984, 23, 4859-4867.
-
(1984)
Biochemistry
, vol.23
, pp. 4859-4867
-
-
Moonen, C.T.W.1
Vervoort, J.2
Müller, F.3
-
30
-
-
0030034038
-
-
Rüterjans, H.; Fleischmann, G.; Löhr, M.; Knauf, F.; Blümel, M.; Lederer, F.; Mayhew, S. G.; Müller, F. Biochem. Soc. Trans. 1996, 24, 116-121.
-
(1996)
Biochem. Soc. Trans.
, vol.24
, pp. 116-121
-
-
Rüterjans, H.1
Fleischmann, G.2
Löhr, M.3
Knauf, F.4
Blümel, M.5
Lederer, F.6
Mayhew, S.G.7
Müller, F.8
-
31
-
-
0017100732
-
-
Yagi, K.; Ohishi, N.; Takai, A.; Kawano, K.; Kyogoku, Y. Biochem. (Tokyo) 1976, 15 (13), 2877-2880.
-
(1976)
Biochem. (Tokyo)
, vol.15
, Issue.13
, pp. 2877-2880
-
-
Yagi, K.1
Ohishi, N.2
Takai, A.3
Kawano, K.4
Kyogoku, Y.5
-
32
-
-
0023005746
-
-
Vervoort, J.; Müller, F.; Mayhew, S. G.; van den Berg, W. A. M.; Moonen, C. T. W.; Bacher, A. Biochemistry 1986, 25, 6789-6799.
-
(1986)
Biochemistry
, vol.25
, pp. 6789-6799
-
-
Vervoort, J.1
Müller, F.2
Mayhew, S.G.3
Van Den Berg, W.A.M.4
Moonen, C.T.W.5
Bacher, A.6
-
33
-
-
21244462222
-
-
Waddell, K. W.; Chekmenev, E.; Wittebort, R. J. J. Am. Chem. Soc. 2005, 127, 9030-9035.
-
(2005)
J. Am. Chem. Soc.
, vol.127
, pp. 9030-9035
-
-
Waddell, K.W.1
Chekmenev, E.2
Wittebort, R.J.3
-
34
-
-
0023261245
-
-
Oas, T. G.; Hartzell, C. J.; Dahlquist, F. W.; Drobny, G. P. J. Am. Chem. Soc. 1987, 109, 5962-5966.
-
(1987)
J. Am. Chem. Soc.
, vol.109
, pp. 5962-5966
-
-
Oas, T.G.1
Hartzell, C.J.2
Dahlquist, F.W.3
Drobny, G.P.4
-
35
-
-
0023261246
-
-
Hartzell, C. J.; Whitfield, M.; Oas, T. G.; Drobny, G. P. J. Am. Chem. Soc. 1987, 109, 5966-5969.
-
(1987)
J. Am. Chem. Soc.
, vol.109
, pp. 5966-5969
-
-
Hartzell, C.J.1
Whitfield, M.2
Oas, T.G.3
Drobny, G.P.4
-
36
-
-
0000848489
-
-
Munovitz, M.; Aue, W. P.; Griffin, R. G. J. Chem. Phys. 1982, 77, 1686-1689.
-
(1982)
J. Chem. Phys.
, vol.77
, pp. 1686-1689
-
-
Munovitz, M.1
Aue, W.P.2
Griffin, R.G.3
-
37
-
-
0027966793
-
-
Gu, Z.; Zambrano, R.; McDermott, A. J. Am. Chem. Soc. 1994, 116, 6368-6372.
-
(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 6368-6372
-
-
Gu, Z.1
Zambrano, R.2
McDermott, A.3
-
38
-
-
0033544398
-
-
Wei, Y.; de Dios, A. C.; McDermott, A. E. J. Am. Chem. Soc. 1999, 121, 10389-10394.
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 10389-10394
-
-
Wei, Y.1
De Dios, A.C.2
McDermott, A.E.3
-
39
-
-
0043043738
-
-
Ramsey, N. F. Phys. Rev. 1950, 78 (6), 699-703.
-
(1950)
Phys. Rev.
, vol.78
, Issue.6
, pp. 699-703
-
-
Ramsey, N.F.1
-
40
-
-
33845316293
-
-
note
-
p is called the paramagnetic contribution because it augments the applied field, not because of any relationship with unpaired electrons.
-
-
-
-
42
-
-
0001675197
-
-
Grant, D. M., Harris, R. K., Eds.; Wiley: Sussex UK
-
Mason, J. In Encyclopedia of NMR; Grant, D. M., Harris, R. K., Eds.; Wiley: Sussex UK, 1996; pp 3222-3251.
-
(1996)
Encyclopedia of NMR
, pp. 3222-3251
-
-
Mason, J.1
-
43
-
-
0000468341
-
-
Lumsden, M. D.; Wu, G.; Wasylishen, R. E.; Curtis, R. D. J. Am. Chem. Soc. 1993, 115 (7), 2825-2832.
-
(1993)
J. Am. Chem. Soc.
, vol.115
, Issue.7
, pp. 2825-2832
-
-
Lumsden, M.D.1
Wu, G.2
Wasylishen, R.E.3
Curtis, R.D.4
-
44
-
-
0030664068
-
-
Solum, M. S.; Altmann, K. L.; Strohmeier, M.; Berges, D. A.; Zhang, Y.; Facelli, J. C.; Pugmire, R. J.; Grant, D. M. J. Am. Chem. Soc. 1997, 119, 9804-9809.
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 9804-9809
-
-
Solum, M.S.1
Altmann, K.L.2
Strohmeier, M.3
Berges, D.A.4
Zhang, Y.5
Facelli, J.C.6
Pugmire, R.J.7
Grant, D.M.8
-
45
-
-
0029942125
-
-
Facelli, J. C.; Pugmire, R. J.; Grant, D. M. J. Am. Chem. Soc. 1996, 118, 5488-5489.
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 5488-5489
-
-
Facelli, J.C.1
Pugmire, R.J.2
Grant, D.M.3
-
47
-
-
0021094366
-
-
Harbison, G. S.; Herzfeld, J.; Griffin, R. G. Biochemistry 1983, 22 (1), 1-5.
-
(1983)
Biochemistry
, vol.22
, Issue.1
, pp. 1-5
-
-
Harbison, G.S.1
Herzfeld, J.2
Griffin, R.G.3
-
49
-
-
0037764903
-
-
Penner, G. H.; Bernard, G. M.; Wasylishen, R. E.; Barrett, A.; Curtis, R. D. J. O. C. 2003, 68, 4258-4264.
-
(2003)
J. O. C.
, vol.68
, pp. 4258-4264
-
-
Penner, G.H.1
Bernard, G.M.2
Wasylishen, R.E.3
Barrett, A.4
Curtis, R.D.5
-
50
-
-
0000699827
-
-
See; Nishino, T., Ed.; Small World Press: Japan
-
A preliminary spectrum was included in a conference proceedings. See Miller, A.-F.; Koder, R. L., Jr.; Walsh, J. D.; Zhang, P.; Haynes, C. A.; Rodgers, D. W. In Flavins and Flavoproteins; Nishino, T., Ed.; Small World Press: Japan, 2005; Vol. 15, pp 261-269.
-
(2005)
Flavins and Flavoproteins
, vol.15
, pp. 261-269
-
-
Miller, A.-F.1
Koder Jr., R.L.2
Walsh, J.D.3
Zhang, P.4
Haynes, C.A.5
Rodgers, D.W.6
-
51
-
-
27544514208
-
-
Nishino, T., Ed.; Small World Press: Japan
-
Miller, A.-F.; Koder, R. L., Jr.; Walsh, J. D.; Zhang, P.; Haynes, C. A.; Rodgers, D. W. In Flavins and Flavoproteins; Nishino, T., Ed.; Small World Press: Japan, 2005.
-
(2005)
Flavins and Flavoproteins
-
-
Miller, A.-F.1
Koder Jr., R.L.2
Walsh, J.D.3
Zhang, P.4
Haynes, C.A.5
Rodgers, D.W.6
-
53
-
-
0012395315
-
-
Tishler, M.; Pfister, K., 3rd; Babson, R. D.; Ladenburg, K.; Fleming, A. J. J. Am. Chem. Soc. 1947, 69, 1487-1492.
-
(1947)
J. Am. Chem. Soc.
, vol.69
, pp. 1487-1492
-
-
Tishler, M.1
Pfister III, K.2
Babson, R.D.3
Ladenburg, K.4
Fleming, A.J.5
-
54
-
-
33646305152
-
-
Bennett, A. E.; Rienstra, C. M.; Auger, M.; Lakshmi, K. V.; Griffin, R. G. J. Chem. Phys. 1995, 103 (16), 6951-6958.
-
(1995)
J. Chem. Phys.
, vol.103
, Issue.16
, pp. 6951-6958
-
-
Bennett, A.E.1
Rienstra, C.M.2
Auger, M.3
Lakshmi, K.V.4
Griffin, R.G.5
-
56
-
-
1242268874
-
-
Cheeseman, J. R.; Trucks, G. W.; Keith, T. A.; Frisch, M. J. J. Chem. Phys. 1996, 104 (14), 5497-5509.
-
(1996)
J. Chem. Phys.
, vol.104
, Issue.14
, pp. 5497-5509
-
-
Cheeseman, J.R.1
Trucks, G.W.2
Keith, T.A.3
Frisch, M.J.4
-
61
-
-
85086294484
-
-
Jameson, C. J.; Jameson, A. K.; Oppusunggu, D.; Wille, S.; Burrell, P. M.; Mason, J. 15N nuclear magnetic shielding scale from gas-phase studies 1981, 74, 81-88.
-
(1981)
15N Nuclear Magnetic Shielding Scale from Gas-phase Studies
, vol.74
, pp. 81-88
-
-
Jameson, C.J.1
Jameson, A.K.2
Oppusunggu, D.3
Wille, S.4
Burrell, P.M.5
Mason, J.6
-
63
-
-
0032209467
-
-
Antzutkin, O. N.; Lee, Y. K.; Levitt, M. H. J. Magn. Reson. 1998, 135 (1), 144-155.
-
(1998)
J. Magn. Reson.
, vol.135
, Issue.1
, pp. 144-155
-
-
Antzutkin, O.N.1
Lee, Y.K.2
Levitt, M.H.3
-
64
-
-
33845326963
-
-
Antzutkin, O. N.; Shekar, S. C.; Levitt, M. H. J. Magn. Reson. A 1995, 115, 7-19.
-
(1995)
J. Magn. Reson. A
, vol.115
, pp. 7-19
-
-
Antzutkin, O.N.1
Shekar, S.C.2
Levitt, M.H.3
-
65
-
-
33845336056
-
-
note
-
N10 is also interesting but is more expensive to label and so will be addressed in future studies.
-
-
-
-
66
-
-
33845287128
-
-
note
-
Spinning sidebands occur at intervals equal to the spinning speed on each side of the isotropic shift, over the spectral width of the signal.
-
-
-
-
67
-
-
33845313836
-
-
note
-
N3 displays biexponential CP buildup kinetics, consistent with heterogeneity among the sites, or motion affecting N3 and/or its attached H. e.g., see ref
-
-
-
-
68
-
-
33845295668
-
-
note
-
The latter possibility is supported by the large improvement in signal intensity obtained at lower temperatures. Similar biexponential buildup in analogous compounds has been reported by Solum et al., ref 47.
-
-
-
-
71
-
-
84860049690
-
-
Eichele, K.; Wasylishen, R. E. http://casgm3.anorg.chemie.uni-tuebingen. de/klaus/soft/index.html, 2005.
-
(2005)
-
-
Eichele, K.1
Wasylishen, R.E.2
-
73
-
-
33845319638
-
-
note
-
1H decoupling.
-
-
-
-
76
-
-
44949276835
-
-
Witanowski, M.; Sicinska, W.; Biernat, S.; Webb, G. A. J. Magn. Reson. 1991, 91, 289-300.
-
(1991)
J. Magn. Reson.
, vol.91
, pp. 289-300
-
-
Witanowski, M.1
Sicinska, W.2
Biernat, S.3
Webb, G.A.4
-
77
-
-
84985069974
-
-
Grande, H. J.; Gast, R.; van Schagen, C. G.; van Berkel, W. J. H.; Müller, F. Helv. Chim. Acta 1977, 60 (2), 367-379.
-
(1977)
Helv. Chim. Acta
, vol.60
, Issue.2
, pp. 367-379
-
-
Grande, H.J.1
Gast, R.2
Van Schagen, C.G.3
Van Berkel, W.J.H.4
Müller, F.5
-
78
-
-
33845286373
-
-
note
-
11s of both strongly reflect the nonbonded lone pair of the N and ring aromaticity. However, the decreased aromaticity of the reduced flavin system, as well as the different ring sizes, complicates comparison between the pyrrole N and the flavin N3 and N10, see ref 47. The issue of aromaticity has been addressed in detail in ref 81. Specifically, in the oxidized state, all three rings were found to be aromatic by the criteria of nucleus-independent chemical shifts, the anisotropy of the magnetic susceptibility, the unified Bird index, and natural bond orbital arguments (ref 81), supporting the possibility of comparing the oxidized flavin N1 and N5 with the N of pyridine, as a simple reference point.
-
-
-
-
79
-
-
0037031681
-
-
Rodriguez-Otero, J.; Martinez-Nunez, E.; Pena-Gallego, A.; Vazquez, S. A. J. O. C. 2002, 67, 6347-6352.
-
(2002)
J. O. C.
, vol.67
, pp. 6347-6352
-
-
Rodriguez-Otero, J.1
Martinez-Nunez, E.2
Pena-Gallego, A.3
Vazquez, S.A.4
-
80
-
-
77956797322
-
-
Academic Press: New York
-
Witanowski, M.; Stefaniak, L.; Webb, G. A. Nitrogen NMR Spectroscopy. Academic Press: New York, 1981; Vol. 11B, p 1-493.
-
(1981)
Nitrogen NMR Spectroscopy
, vol.11 B
, pp. 1-493
-
-
Witanowski, M.1
Stefaniak, L.2
Webb, G.A.3
-
82
-
-
0001753654
-
-
Shinkai, S.; Honda, N.; Ishikawa, Y.; Manabe, O. J. Am. Chem. Soc. 1985, 107, 6286-6292.
-
(1985)
J. Am. Chem. Soc.
, vol.107
, pp. 6286-6292
-
-
Shinkai, S.1
Honda, N.2
Ishikawa, Y.3
Manabe, O.4
-
85
-
-
0001669148
-
-
Platenkamp, R. J.; Palmer, M. H.; Visser, A. J. W. G. Eur. Biophys. J. 1987, 14, 393-402.
-
(1987)
Eur. Biophys. J.
, vol.14
, pp. 393-402
-
-
Platenkamp, R.J.1
Palmer, M.H.2
Visser, A.J.W.G.3
-
86
-
-
0023658602
-
-
Hall, L. H.; Bowers, M. L.; Dufor, C. N. Biochemistry 1987, 26, 7401-7409.
-
(1987)
Biochemistry
, vol.26
, pp. 7401-7409
-
-
Hall, L.H.1
Bowers, M.L.2
Dufor, C.N.3
-
88
-
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note
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The important reactivity of the C4a site is manifest in the reduced state, which is not the focus of this work.
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