2014
DOI: 10.1021/ja506914p
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Design and Synthesis of Epicocconone Analogues with Improved Fluorescence Properties

Abstract: Epicocconone is a natural latent fluorophore that is widely used in biotechnology because of its large Stokes shift and lack of fluorescence in its unconjugated state. However, the low photostability and quantum yields of epicocconone have limited its wider use, and in the absence of a total synthesis, this limitation has been a long-standing problem. Here we report a general strategy for the synthesis of epicocconone analogues that relies on a 2-iodoxybenzoic acid-mediated dearomatization and on the replaceme… Show more

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Cited by 38 publications
(45 citation statements)
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“…Excitation/emission spectra were recorded under the same conditions after emission/excitation at the corresponding wavelength (520/430 nm, excitation and emission filters: auto, excitation and emission slit=5 nm). Fluorescence quantum yields were measured at 25 °C by a relative method that used Lucifer yellow ( Φ F =21 % in water, 430 nm) as a standard . The following Equation was used to determine the relative fluorescence quantum yield in which A is the absorbance (in the range of 0.01–0.1 a.u.…”
Section: Methodsmentioning
confidence: 99%
“…Excitation/emission spectra were recorded under the same conditions after emission/excitation at the corresponding wavelength (520/430 nm, excitation and emission filters: auto, excitation and emission slit=5 nm). Fluorescence quantum yields were measured at 25 °C by a relative method that used Lucifer yellow ( Φ F =21 % in water, 430 nm) as a standard . The following Equation was used to determine the relative fluorescence quantum yield in which A is the absorbance (in the range of 0.01–0.1 a.u.…”
Section: Methodsmentioning
confidence: 99%
“…The β‐keto‐dioxinones 4 a – c and 5 a – c will bear different R 1 ( n ‐C 4 H 9 , CH 2 CH 2 OMe ) and R 2 (H, p PhOMe, p PhNPh 2 ) groups in order to study their influence on fluorescence and solubility. Bicyclic keto‐alcohol 3 will be prepared as already reported by us …”
Section: Resultsmentioning
confidence: 99%
“…The completion of the synthesis of the fluorenyl epicocconone analogues was realized by condensation of dioxinones 4 and 5 with the bicyclic keto‐alcohol 3 , via thermal fragmentation of dioxinones to an acylketene, following our reported procedure (Scheme ) . Then heating a mixture of dioxinones 4 a – c or 5 a – c and ketoalcohol 3 in toluene for 30 minutes followed by addition of triethylamine gave a series of linear lactones 24 a – c and 25 a – c , albeit in much lower yields than usually obtained with dioxinones substituted by simple aromatic rings…”
Section: Resultsmentioning
confidence: 99%
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“…It interacts noncovalently with SDS and proteins . Epicocconone is also available as a synthetic compound . Epicocconone‐based stainings are also referred to as Deep Purple, Lava Purple, or SERVA Purple.…”
Section: Proposed Total Protein Stainings and Their Propertiesmentioning
confidence: 99%