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Volumn 131, Issue 32, 2009, Pages 11590-11605

Structure and spectroscopy of oxyluciferin, the light emitter of the firefly bioluminescence

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION MAXIMA; ACTIVE SITE; ADENOSINE MONOPHOSPHATE; AQUEOUS SOLUTIONS; BLUE EMITTER; CHEMICAL EQUILIBRIUMS; CHEMICAL FORMS; CHEMICAL SPECIES; CONCENTRATION RATIO; CONJUGATED ACIDS; DENSITY-FUNCTIONAL CALCULATIONS; DIANIONS; EMISSION BANDS; EMISSION SPECTRAL; ENOLATES; FLUORESCENCE SPECTRA; GREEN REGIONS; GROUND-STATE; HYDROGEN BONDINGS; HYDROGEN-BONDED DIMERS; INTERMOLECULAR INTERACTIONS; LIGHT EMITTERS; NMR DATA; SOLVENT POLARITY; STEADY-STATE ABSORPTION; TIME-RESOLVED FLUORESCENCE; WILD TYPES;

EID: 68849087538     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja904309q     Document Type: Article
Times cited : (169)

References (82)
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    • fl are the chemical yield of the reaction, the proportion of the product molecules which are produced as excited, and the fluorescence yield, respectively.
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    • The earlier reported value of 88 ( 25%: (a) Seliger, H. H.; McElroy, W. D. Arch. Biochem. Biophys. 1960, 88, 136.
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    • 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%.
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    • In the earlier literature: (a) Koo, J.-Y.; Schmidt, S. P.; Schuster, G. B. Proc. Natl. Acad. Sci. U.S.A. 1978, 75, 30.
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    • (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.
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    • 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
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    • 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
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    • 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.
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    • 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.
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.