-
5
-
-
0032451343
-
-
(b) Price, R. L.; Squirrell, D. J.; Murphy, M. J. J. Clin. Ligand Assay 1998, 21, 349.
-
(1998)
J. Clin. Ligand Assay
, vol.21
, pp. 349
-
-
Price, R.L.1
Squirrell, D.J.2
Murphy, M.J.3
-
7
-
-
0033631082
-
-
(d) Ohkuma, H.; Abe, K.; Kosaka, Y.; Maeda, M. Luminescence 2000, 15, 21.
-
(2000)
Luminescence
, vol.15
, pp. 21
-
-
Ohkuma, H.1
Abe, K.2
Kosaka, Y.3
Maeda, M.4
-
9
-
-
33748785208
-
-
(b) Shinde, R.; Perkins, J.; Contag, C. H. Biochemistry 2006, 45, 11103.
-
(2006)
Biochemistry
, vol.45
, pp. 11103
-
-
Shinde, R.1
Perkins, J.2
Contag, C.H.3
-
11
-
-
68849129580
-
-
fl are the chemical yield of the reaction, the proportion of the product molecules which are produced as excited, and the fluorescence yield, respectively.
-
fl are the chemical yield of the reaction, the proportion of the product molecules which are produced as excited, and the fluorescence yield, respectively.
-
-
-
-
12
-
-
0000372063
-
-
The earlier reported value of 88 ( 25%: (a) Seliger, H. H.; McElroy, W. D. Arch. Biochem. Biophys. 1960, 88, 136.
-
The earlier reported value of 88 ( 25%: (a) Seliger, H. H.; McElroy, W. D. Arch. Biochem. Biophys. 1960, 88, 136.
-
-
-
-
13
-
-
0001935545
-
-
Selinger, H. H.; McElroy, W. D. Biochem. Biophys. Res. Commun. 1959, 1, 21. was recently re-determined and corrected to 41.0 7.4%.
-
(b) Selinger, H. H.; McElroy, W. D. Biochem. Biophys. Res. Commun. 1959, 1, 21. was recently re-determined and corrected to 41.0 ( 7.4%.
-
-
-
-
14
-
-
37549048641
-
-
(c) Ando, Y.; Niwa, K.; Yamada, N.; Enomoto, T.; Irie, T.; Kubota, H.; Ohmiya, Y.; Akiyama, H. Nat. Photonics 2007, 2, 44.
-
(2007)
Nat. Photonics
, vol.2
, pp. 44
-
-
Ando, Y.1
Niwa, K.2
Yamada, N.3
Enomoto, T.4
Irie, T.5
Kubota, H.6
Ohmiya, Y.7
Akiyama, H.8
-
16
-
-
0002552327
-
-
White, E. H.; Rapaport, E.; Seliger, H. H.; Hopkins, T. A. Bioorg. Chem. 1971, 1, 92.
-
(1971)
Bioorg. Chem
, vol.1
, pp. 92
-
-
White, E.H.1
Rapaport, E.2
Seliger, H.H.3
Hopkins, T.A.4
-
18
-
-
18044374474
-
-
Nakamura, M.; Maki, S.; Amano, Y.; Ohkita, Y.; Niwa, K.; Hirano, T.; Ohmiya, Y.; Niwa, H. Biochem. Biophys. Res. Commun. 2005, 331, 471.
-
(2005)
Biochem. Biophys. Res. Commun
, vol.331
, pp. 471
-
-
Nakamura, M.1
Maki, S.2
Amano, Y.3
Ohkita, Y.4
Niwa, K.5
Hirano, T.6
Ohmiya, Y.7
Niwa, H.8
-
23
-
-
0014403429
-
-
Plant, P. J.; White, E. H.; McElroy, W. D. Biochem. Biophys. Res. Commun. 1968, 31, 98.
-
(1968)
Biochem. Biophys. Res. Commun
, vol.31
, pp. 98
-
-
Plant, P.J.1
White, E.H.2
McElroy, W.D.3
-
24
-
-
0002313888
-
-
In the earlier literature: (a) Koo, J.-Y, Schmidt, S. P, Schuster, G. B. Proc. Natl. Acad. Sci. U.S.A. 1978, 75, 30
-
In the earlier literature: (a) Koo, J.-Y.; Schmidt, S. P.; Schuster, G. B. Proc. Natl. Acad. Sci. U.S.A. 1978, 75, 30.
-
-
-
-
25
-
-
33847089828
-
-
Koo, J.-y, Schuster, G. B. J. Am. Chem. Soc. 1977, 99, 6107. a chemically initiated electron exchange luminescence (CIEEL) mechanism has been invoked to explain the emission of light from the dioxetanone, according to which intramolecular electron transfer occurs from the polycyclic heterocyclic portion of the molecule to the dioxetanone part, whereby an intermediate diradical anion is creation and decomposed. This mechanism, however, has been discredited in the more recent reports based on quantum yield considerations. We thank the anonymous reviewer for bringing this to our attention
-
(b) Koo, J.-y.; Schuster, G. B. J. Am. Chem. Soc. 1977, 99, 6107. a "chemically initiated electron exchange luminescence (CIEEL)" mechanism has been invoked to explain the emission of light from the dioxetanone, according to which intramolecular electron transfer occurs from the polycyclic heterocyclic portion of the molecule to the dioxetanone part, whereby an intermediate diradical anion is creation and decomposed. This mechanism, however, has been discredited in the more recent reports based on quantum yield considerations. We thank the anonymous reviewer for bringing this to our attention.
-
-
-
-
26
-
-
49549155001
-
-
Okada, K.; Iio, H.; Kubota, I.; Goto, T. Tetrahedron Lett. 1974, 32, 2771.
-
(1974)
Tetrahedron Lett
, vol.32
, pp. 2771
-
-
Okada, K.1
Iio, H.2
Kubota, I.3
Goto, T.4
-
29
-
-
77955813634
-
-
Blank, G. E.; Pletcher, J.; Sax, M. Acta Crystallogr. 1974, B30, 2525.
-
(1974)
Acta Crystallogr
, vol.B30
, pp. 2525
-
-
Blank, G.E.1
Pletcher, J.2
Sax, M.3
-
30
-
-
0015211209
-
-
Blank, G. E.; Pletcher, J.; Sax, M. Biochem. Biophys. Res. Commun. 1971, 42, 583.
-
(1971)
Biochem. Biophys. Res. Commun
, vol.42
, pp. 583
-
-
Blank, G.E.1
Pletcher, J.2
Sax, M.3
-
31
-
-
49649134367
-
-
Suzuki, N.; Sato, M.; Okada, K.; Goto, T. Tetrahedron 1972, 28, 4065.
-
(1972)
Tetrahedron
, vol.28
, pp. 4065
-
-
Suzuki, N.1
Sato, M.2
Okada, K.3
Goto, T.4
-
33
-
-
0642338702
-
-
Wada, N.; Mitsuta, K.; Kohno, M.; Suzuki, N. J. Phys. Soc. Jpn. 1989, 58, 3501.
-
(1989)
J. Phys. Soc. Jpn
, vol.58
, pp. 3501
-
-
Wada, N.1
Mitsuta, K.2
Kohno, M.3
Suzuki, N.4
-
34
-
-
0042224032
-
Moscow Univ
-
Brovko, L. Y.; Cherednikova, E. Y.; Chikishev, A. Y.; Chudinova, E. A. Moscow Univ. Trans. Phys. Astron. Ser. 1998, 3, 26.
-
(1998)
Trans. Phys. Astron. Ser
, vol.3
, pp. 26
-
-
Brovko, L.Y.1
Cherednikova, E.Y.2
Chikishev, A.Y.3
Chudinova, E.A.4
-
37
-
-
0027236124
-
-
Gandelman, O. A.; Brovko, L. Y.; Ugarova, N. N.; Chikishev, A. Y.; Shkurimov, A. P. J. Photochem. Photobiol. 1993, B19, 187.
-
(1993)
J. Photochem. Photobiol
, vol.B19
, pp. 187
-
-
Gandelman, O.A.1
Brovko, L.Y.2
Ugarova, N.N.3
Chikishev, A.Y.4
Shkurimov, A.P.5
-
38
-
-
33644665186
-
-
Leont'eva, O. V.; Vlasova, T. N.; Ugarova, N. N. Biochemistry (Moscow) 2006, 71, 51.
-
(2006)
Biochemistry (Moscow)
, vol.71
, pp. 51
-
-
Leont'eva, O.V.1
Vlasova, T.N.2
Ugarova, N.N.3
-
39
-
-
33744512859
-
-
Vlasova, T. N.; Leontieva, O. V.; Ugarova, N. N. Biochemistry (Moscow) 2006, 71, 555.
-
(2006)
Biochemistry (Moscow)
, vol.71
, pp. 555
-
-
Vlasova, T.N.1
Leontieva, O.V.2
Ugarova, N.N.3
-
40
-
-
67849102207
-
-
Hirano, T.; Hasumi, Y.; Ohtsuka, K.; Maki, S.; Niwa, H.; Yamaji, M.; Hashizume, D. J. Am. Chem. Soc. 2009, 131, 2385.
-
(2009)
J. Am. Chem. Soc
, vol.131
, pp. 2385
-
-
Hirano, T.1
Hasumi, Y.2
Ohtsuka, K.3
Maki, S.4
Niwa, H.5
Yamaji, M.6
Hashizume, D.7
-
41
-
-
0003540262
-
-
Herring, P. J, Ed, Academic Press: New York
-
(a) Lloyd, J. E. In Bioluminescence in Action; Herring, P. J., Ed.; Academic Press: New York, 1978; pp 241-272.
-
(1978)
Bioluminescence in Action
, pp. 241-272
-
-
Lloyd, J.E.1
-
42
-
-
0003471941
-
-
Sperelakis, N, Ed, Academic Press: New York
-
(b) Hastings, J. W. In Cell Physiology Source Book; Sperelakis, N., Ed.; Academic Press: New York, 1995; pp 665-681.
-
(1995)
Cell Physiology Source Book
, pp. 665-681
-
-
Hastings, J.W.1
-
43
-
-
0024967767
-
-
(a) Wood, K. V.; Lam, Y. A.; Seliger, H. H.; McElroy, W. D. Science 1989, 244, 700.
-
(1989)
Science
, vol.244
, pp. 700
-
-
Wood, K.V.1
Lam, Y.A.2
Seliger, H.H.3
McElroy, W.D.4
-
45
-
-
0032858233
-
-
Branchini, B. R.; Magyar, R. A.; Murtiashaw, M. H.; Andreson, S. M.; Helgerson, L. C.; Zimmer, M. Biochemistry 1999, 38, 13223.
-
(1999)
Biochemistry
, vol.38
, pp. 13223
-
-
Branchini, B.R.1
Magyar, R.A.2
Murtiashaw, M.H.3
Andreson, S.M.4
Helgerson, L.C.5
Zimmer, M.6
-
46
-
-
0037070540
-
-
(a) Branchini, B. R.; Murtiashaw, M. H.; Magyar, R. A.; Portier, N. C.; Ruggiero, M. C.; Stroh, J. G. J. Am. Chem. Soc. 2002, 124, 2112.
-
(2002)
J. Am. Chem. Soc
, vol.124
, pp. 2112
-
-
Branchini, B.R.1
Murtiashaw, M.H.2
Magyar, R.A.3
Portier, N.C.4
Ruggiero, M.C.5
Stroh, J.G.6
-
47
-
-
2942562205
-
-
(b) Branchini, B. R.; Southworth, T. L.; Murtiashaw, M. H.; Magyar, R. A.; Gonzalez, S. A.; Ruggiero, M. C.; Stroh, J. G. Biochemistry 2004, 43, 7255.
-
(2004)
Biochemistry
, vol.43
, pp. 7255
-
-
Branchini, B.R.1
Southworth, T.L.2
Murtiashaw, M.H.3
Magyar, R.A.4
Gonzalez, S.A.5
Ruggiero, M.C.6
Stroh, J.G.7
-
48
-
-
0035957085
-
-
Branchini, B. R.; Magyar, R. A.; Murtiashaw, M. H.; Portier, N. C. Biochemistry 2001, 40, 2410.
-
(2001)
Biochemistry
, vol.40
, pp. 2410
-
-
Branchini, B.R.1
Magyar, R.A.2
Murtiashaw, M.H.3
Portier, N.C.4
-
49
-
-
34247881853
-
-
Tafreshi, N.Kh.; Hosseinkhani, S.; Sadeghizadeh, M.; Sadeghi, M.; Ranjbar, B.; Naderi-Manesh, H. J. Biol. Chem. 2007, 282, 8641.
-
(2007)
J. Biol. Chem
, vol.282
, pp. 8641
-
-
Tafreshi, N.K.1
Hosseinkhani, S.2
Sadeghizadeh, M.3
Sadeghi, M.4
Ranjbar, B.5
Naderi-Manesh, H.6
-
50
-
-
29144434664
-
-
Ugarova, N. N.; Maloshenok, L. G.; Uporov, I. V.; Koksharov, M. I. Biochemistry (Moscow) 2005, 70, 1262.
-
(2005)
Biochemistry (Moscow)
, vol.70
, pp. 1262
-
-
Ugarova, N.N.1
Maloshenok, L.G.2
Uporov, I.V.3
Koksharov, M.I.4
-
51
-
-
0030584662
-
-
Conti, E.; Franks, N. P.; Bricks, P. Structure 1996, 4, 287.
-
(1996)
Structure
, vol.4
, pp. 287
-
-
Conti, E.1
Franks, N.P.2
Bricks, P.3
-
52
-
-
33645038011
-
-
Nakatsu, T.; Ichiyama, S.; Hiratake, J.; Saldanha, A.; Kobashi, N.; Sakata, K.; Kato, H. Nature 2006, 440, 372.
-
(2006)
Nature
, vol.440
, pp. 372
-
-
Nakatsu, T.1
Ichiyama, S.2
Hiratake, J.3
Saldanha, A.4
Kobashi, N.5
Sakata, K.6
Kato, H.7
-
53
-
-
68849092535
-
-
2 would appear in the elemental analysis results as 0.5 water molecules per formula unit.
-
2 would appear in the elemental analysis results as 0.5 water molecules per formula unit.
-
-
-
-
54
-
-
68849129579
-
-
Basic crystallographic data: OxyLH2, C 10H6N2O2S2, monoclinic, P21/n, a, 4.8806(4, b, 18.8242(14, c, 11.1298(8) Å, β, 99.260(5)°, V, 1009.21(13) Å3, Z, 4, Θmax, 26.4°, GoF, 1.037, R1[I > 2σ(I, 0.0524, wR2, 0.1239. MOxyLH2, C11H 8N2O2S2, monoclinic, P2 1/n, a, 6.3027(4, b, 14.8046(10, c, 11.6515(7) Å, β, 91.419(4)°, V, 1086.86(12) Å3, Z, 4, Θmax, 27.5°, GoF, 1.069, R1[I > 2σI, 0.0337, wR2, 0.0875
-
2 = 0.0875.
-
-
-
-
55
-
-
34548427946
-
-
Nakatani, N.; Hasegawa, J.; Nakatsuji, H. J. Am. Chem. Soc. 2007, 129, 8756.
-
(2007)
J. Am. Chem. Soc
, vol.129
, pp. 8756
-
-
Nakatani, N.1
Hasegawa, J.2
Nakatsuji, H.3
-
57
-
-
54849405354
-
-
Li, Z.; Ren, A.; Guo, J.; Yang, T.; Goddard, J. D.; Feng, J. J. Phys. Chem. 2008, 112, 9796.
-
(2008)
J. Phys. Chem
, vol.112
, pp. 9796
-
-
Li, Z.1
Ren, A.2
Guo, J.3
Yang, T.4
Goddard, J.D.5
Feng, J.6
-
58
-
-
39749091244
-
-
Ren, A.; Guo, J.; Feng, J.; Zou, L.; Li, Z.; Goddard, J. D. Chin. J. Chem. 2008, 26, 55.
-
(2008)
Chin. J. Chem
, vol.26
, pp. 55
-
-
Ren, A.1
Guo, J.2
Feng, J.3
Zou, L.4
Li, Z.5
Goddard, J.D.6
-
60
-
-
0035538671
-
-
(a) Yoshida, K.; Uwada, K.; Kumaoka, H.; Bu, L.; Watanabe, S. Chem. Lett. 2001, 30, 808.
-
(2001)
Chem. Lett
, vol.30
, pp. 808
-
-
Yoshida, K.1
Uwada, K.2
Kumaoka, H.3
Bu, L.4
Watanabe, S.5
-
61
-
-
62849099066
-
-
(b) Dong., J.; Solntsev, K. M.; Tolbert, L. J. Am. Chem. Soc. 2009, 131, 662.
-
(2009)
J. Am. Chem. Soc
, vol.131
, pp. 662
-
-
Dong, J.1
Solntsev, K.M.2
Tolbert, L.3
-
62
-
-
0035851393
-
-
Esteves da Silva, J. C. G.; Magalhaes, J. M. C. S.; Fontes, R. Tetrahedron Lett. 2001, 42, 8173.
-
(2001)
Tetrahedron Lett
, vol.42
, pp. 8173
-
-
Esteves da Silva, J.C.G.1
Magalhaes, J.M.C.S.2
Fontes, R.3
-
63
-
-
68849097027
-
-
The solvent parameters for calculation of Δf were taken from: (a) Reichardt, C. Solvents and solvent effects in organic chemistry, 3rd ed.; Wiley-VCH: Weinheim, 2003.
-
The solvent parameters for calculation of Δf were taken from: (a) Reichardt, C. Solvents and solvent effects in organic chemistry, 3rd ed.; Wiley-VCH: Weinheim, 2003.
-
-
-
-
65
-
-
0001444812
-
-
(c) Mataga, N.; Kaifu, Y.; Koizumi, M. Bull. Chem. Soc. Jpn. 1956, 29, 465.
-
(1956)
Bull. Chem. Soc. Jpn
, vol.29
, pp. 465
-
-
Mataga, N.1
Kaifu, Y.2
Koizumi, M.3
-
67
-
-
0013695572
-
-
Gandel'man, O. A.; Brovko, L. Yu.; Ugarova, N. N.; Shchegolev, A. A. Biochemistry (Moscow) 1990, 55, 785.
-
(1990)
Biochemistry (Moscow)
, vol.55
, pp. 785
-
-
Gandel'man, O.A.1
Brovko, L.Y.2
Ugarova, N.N.3
Shchegolev, A.A.4
-
68
-
-
0042079957
-
-
Cormier, M. J, Hercules, D. M, Lee, J, Eds, Plenum Press: New York
-
Goto, T.; Kubota, I.; Suzuki, N.; Kishi, Y.; Inoue, S. In Chemiluminescence and Bioluminescence; Cormier, M. J., Hercules, D. M., Lee, J., Eds.; Plenum Press: New York, 1973; pp 325-335.
-
(1973)
Chemiluminescence and Bioluminescence
, pp. 325-335
-
-
Goto, T.1
Kubota, I.2
Suzuki, N.3
Kishi, Y.4
Inoue, S.5
-
69
-
-
0033609034
-
-
Elsliger, M.-A.; Wachter, R. M.; Hanson, G. T.; Kallio, K.; Remington, J. S. Biochemistry 1999, 38, 5296.
-
(1999)
Biochemistry
, vol.38
, pp. 5296
-
-
Elsliger, M.-A.1
Wachter, R.M.2
Hanson, G.T.3
Kallio, K.4
Remington, J.S.5
-
70
-
-
0014668723
-
-
White, E. H.; Rapaport, E.; Hopkins, T. A.; Selkinger, H. H. J. Am. Chem. Soc. 1969, 91, 2178.
-
(1969)
J. Am. Chem. Soc
, vol.91
, pp. 2178
-
-
White, E.H.1
Rapaport, E.2
Hopkins, T.A.3
Selkinger, H.H.4
-
71
-
-
0003026011
-
-
Campbell, A. K, Kricka, L. J, Stanley, P. E, Eds, John Wiley & Sons: Chichester, UK
-
McCapra, F.; Gilfoyle, D. J.; Young, D. W.; Church, N. J.; Spencer, P. In Bioluminescence and Chemiluminescence. Fundamentals and Applied Aspects; Campbell, A. K., Kricka, L. J., Stanley, P. E., Eds.; John Wiley & Sons: Chichester, UK, 1994; p 387.
-
(1994)
Bioluminescence and Chemiluminescence. Fundamentals and Applied Aspects
, pp. 387
-
-
McCapra, F.1
Gilfoyle, D.J.2
Young, D.W.3
Church, N.J.4
Spencer, P.5
-
72
-
-
68849129890
-
-
It should be noted, however, that unlike the real intermediate luciferyl adenylate, in which the oxyluciferin residue is flexibly bound to the rest of the molecule, the model dehydroluciferyl ester is fixed to planarity by the hybridization at the atom C4, and it also includes sulfonylamido instead of phosphate group. These differences might result in different interactions with the environment due to the decreased flexibility of the model intermediate
-
It should be noted, however, that unlike the real intermediate (luciferyl adenylate), in which the oxyluciferin residue is flexibly bound to the rest of the molecule, the model dehydroluciferyl ester is fixed to planarity by the hybridization at the atom C4, and it also includes sulfonylamido instead of phosphate group. These differences might result in different interactions with the environment due to the decreased flexibility of the model intermediate.
-
-
-
-
73
-
-
68849099330
-
-
APEX2 (Ver. 2.1-4) and SAINT Ver. 7.34A, Bruker AXS Inc, Madison, WI, 2007
-
APEX2 (Ver. 2.1-4) and SAINT (Ver. 7.34A); Bruker AXS Inc.: Madison, WI, 2007.
-
-
-
-
74
-
-
0004283942
-
-
University of Göttingen: Göttingen, Germany
-
Sheldrick, G. M. SADABS; University of Göttingen: Göttingen, Germany, 1996.
-
(1996)
SADABS
-
-
Sheldrick, G.M.1
-
76
-
-
0000604488
-
-
(b) Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A.; Burla, M. C.; Polidori, G.; Camalli, M. J. Appl. Crystallogr. 1994, 27, 435.
-
(1994)
J. Appl. Crystallogr
, vol.27
, pp. 435
-
-
Altomare, A.1
Cascarano, G.2
Giacovazzo, C.3
Guagliardi, A.4
Burla, M.C.5
Polidori, G.6
Camalli, M.7
-
77
-
-
0004150157
-
-
University of Göttingen: Göttingen, Germany
-
Sheldrick, G. M. E. SHELXL-97; University of Göttingen: Göttingen, Germany, 1997.
-
(1997)
SHELXL-97
-
-
Sheldrick, G.M.E.1
-
79
-
-
0000438847
-
-
Lapinski, L.; Rostkowska, H.; Nowak, M. J.; Kwiatkowski, J. S.; Leszczynski, J. Vib. Spectrosc. 1996, 13, 23.
-
(1996)
Vib. Spectrosc
, vol.13
, pp. 23
-
-
Lapinski, L.1
Rostkowska, H.2
Nowak, M.J.3
Kwiatkowski, J.S.4
Leszczynski, J.5
-
80
-
-
11644290052
-
-
Hess, B. A.; Schaad, L. J.; Ćarsky, P.; Zahradník, R. Chem. Rev. 1986, 86, 709.
-
(1986)
Chem. Rev
, vol.86
, pp. 709
-
-
Hess, B.A.1
Schaad, L.J.2
Ćarsky, P.3
Zahradník, R.4
-
81
-
-
68849120018
-
-
Frisch, M. J.; et al. Gaussian03; Gaussian, Inc.: Wallingford, CT, 2004 (the complete reference is provided as Supporting Information).
-
Frisch, M. J.; et al. Gaussian03; Gaussian, Inc.: Wallingford, CT, 2004 (the complete reference is provided as Supporting Information).
-
-
-
-
82
-
-
34247496846
-
-
University of Western Australia: Perth, Australia
-
Wolff, S. K.; Grimwood, D. J.; McKinnon, J. J.; Jayatilaka, D.; Spackman, M. A. CrystalExplorer; University of Western Australia: Perth, Australia, 2007.
-
(2007)
CrystalExplorer
-
-
Wolff, S.K.1
Grimwood, D.J.2
McKinnon, J.J.3
Jayatilaka, D.4
Spackman, M.A.5
|