Studies in the Tropolone Series. I. Thujaplicins and Nootkatin.

Aulin-Erdtman, Gunhild; Hassel, O.; Webb, M. J.; Rottenberg, Max

doi:10.3891/acta.chem.scand.04-1031

Cited by 20 publications

(12 citation statements)

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“…1H NMR spectra unambiguously show that, :.fter irradiation of trans-p-coumaric acid with UV light, trans-cis isomerization occurs, as was previously demonstrated for this and other cinnamic acid derivatives [17][18][19]. Fig.…”

Section: Photo-isomerization Of Pcoumaric Acid In Aqueous Solutionsupporting

confidence: 66%

“…12 ILA. On-cohmm detection was performed at 284 and 265 nm, the wavelengths of maximal absorbance of trans-and c/s-p-coumaric acid, respectively [17].…”

Section: Methodsmentioning

confidence: 99%

“…2B cannot directly be calculated from the ratio of the peak area of each isomer, because of their ,,~dely different extinction coefficients in the UV region. The molar extinction coefficient at 284 nm is significantly lower for the cis isomer, as compared to trans-p-coumaric acid [17]. Using the proper extinction coefficients, the ratio of the two isomers, as present in the mixture analyzed in the experi- ment shown in Fig.…”

Section: Photo-isomerization Of Pcoumaric Acid In Aqueous Solutionmentioning

confidence: 99%

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Evidence for trans‐cis isomerization of the p‐coumaric acid chromophore as the photochemical basis of the photocycle of photoactive yellow protein

et al. 1996

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Analysis of the chromophore p-coumaric acid, extracted from the ground state and the long-lived blue-shifted photocycle intermediate of photoactive yellow protein, shows that the chromophore is reversibly converted from the trans to the cis configuration, while progressing through the photocycle. The detection of the trans and ¢is isomers was carried out by high performance capillary zone electrophoresis and further substantiated by tH NMR spectroscopy. The data presented here establish the photo.isomerization of the vinyl double bond in the chromophore as the photochemical basis for the photocycle of photoactive yellow protein, a euhacterlal photosensory protein. A similar isomerization process occurs in the structurally very different sensory rhodopsins, offering an explanatimJ for the strong spectroscopic similarities between photoactive yellow protein and the sensory rhodopsins. This is the first demonstration of light-induced isomerization of a chromophore double bond as the photochemical basis for photosensing in the domain of Bacteria.

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Section: Photo-isomerization Of Pcoumaric Acid In Aqueous Solutionsupporting

confidence: 66%

“…12 ILA. On-cohmm detection was performed at 284 and 265 nm, the wavelengths of maximal absorbance of trans-and c/s-p-coumaric acid, respectively [17].…”

Section: Methodsmentioning

confidence: 99%

Section: Photo-isomerization Of Pcoumaric Acid In Aqueous Solutionmentioning

confidence: 99%

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Evidence for trans‐cis isomerization of the p‐coumaric acid chromophore as the photochemical basis of the photocycle of photoactive yellow protein

et al. 1996

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“…The photoproduct can be attributed to the cis isomer by comparison with spectra reported for trans-p-coumaric acid. [28,43]…”

Section: Resultsmentioning

confidence: 99%

Ultrafast Photoisomerization of Photoactive Yellow Protein Chromophore Analogues in Solution: Influence of the Protonation State

et al. 2006

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We investigate solvent viscosity and polarity effects on the photoisomerization of the protonated and deprotonated forms of two analogues of the photoactive yellow protein (PYP) chromophore. These are trans-p-hydroxybenzylidene acetone and trans-p-hydroxyphenyl cinnamate, studied in solutions of different polarity and viscosity at room temperature, by means of femtosecond fluorescence up-conversion. The fluorescence lifetimes of the protonated forms are found to be barely sensitive to solvent viscosity, and to increase with increasing solvent polarity. In contrast, the fluorescence decays of the deprotonated forms are significantly slowed down in viscous media and accelerated in polar solvents. These results elucidate the dramatic influence of the protonation state of the PYP chromophore analogues on their photoinduced dynamics. The viscosity and polarity effects are, respectively, interpreted in terms of different isomerization coordinates and charge redistribution in S(1). A trans-to-cis isomerization mechanism involving mainly the ethylenic double-bond torsion and/or solvation is proposed for the anionic forms, whereas "concerted" intramolecular motions are proposed for the neutral forms.

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“…15, 16, and 17), while they bear a striking resemblance respectively to those of o-, m-, and pcins). (23) Similarly the vibrational structures of the spectra of o-and p-methyl tropolones…”

Section: Introductionmentioning

confidence: 99%

Ultraviolet Absorption Spectra of Troponoids

Tsuboi

1952

Bulletin of the Chemical Society of Japan

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Studies in the Tropolone Series. I. Thujaplicins and Nootkatin.

Cited by 20 publications

References 0 publications

Evidence for trans‐cis isomerization of the p‐coumaric acid chromophore as the photochemical basis of the photocycle of photoactive yellow protein

Evidence for trans‐cis isomerization of the p‐coumaric acid chromophore as the photochemical basis of the photocycle of photoactive yellow protein

Ultrafast Photoisomerization of Photoactive Yellow Protein Chromophore Analogues in Solution: Influence of the Protonation State

Ultraviolet Absorption Spectra of Troponoids

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