Bhc-diol as a Photolabile Protecting Group for Aldehydes and Ketones

Lü, Min; Fedoryak, Olesya D.; Moister, Brent R.; Dore, Timothy M.

doi:10.1021/ol034536b

Cited by 110 publications

(91 citation statements)

References 19 publications

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“…Figure 4a displays typical experimental FCS autocorrelation functions G(t) that were recorded on a 1 mm 10 c solution in CH 3 CN/20 mm Tris pH 9 buffer 1:1 (v/v) that was submitted to increasing input-laser powers. Throughout this study, we always obtained satisfactory fits of the experimental points by using Equation (14) that is associated with a nonreactive mixture of two fluorescent species. As anticipated from the similar sizes of the caged derivatives and the released substrates, the calculated diffusion times t D were essentially independent of laser powers below 15 mW at the sample level.…”

Section: Linear Absorption and Emission Propertiesmentioning

confidence: 81%

“…Thus, we considered the approximate correlation function [Eq. (14)] with fewer undetermined constants to fit experimental data:…”

Section: Methodsmentioning

confidence: 99%

“…In the fitting process using Equation (14), N tot was assumed from the concentration used in nc and of the illuminated volume from a preliminary calibration, [56] and only …”

Section: Methodsmentioning

confidence: 99%

“…The 1 GM range has already been obtained. [7,8,14] In principle, 10-100 GM ranges in wavelength available from current-pulsed IR laser sources could be reached for reasonably "small" molecules by combining the largest ever observed values for the cross-section for twophoton absorption [15,16] with the uncaging quantum yields. Among the available photoremovable protecting groups, the 2-nitrobenzyl functionality has gained wide acceptance and most of the caged biologically active compounds that have been synthesized belong to this series.…”

Section: Introductionmentioning

confidence: 99%

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o‐Nitrobenzyl Photolabile Protecting Groups with Red‐Shifted Absorption: Syntheses and Uncaging Cross‐Sections for One‐ and Two‐Photon Excitation

Aujard

Benbrahim

Gouget

et al. 2006

Chemistry A European J

291

292

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We evaluated the o-nitrobenzyl platform for designing photolabile protecting groups with red-shifted absorption that could be photolyzed upon one- and two-photon excitation. Several synthetic pathways to build different conjugated o-nitrobenzyl backbones, as well as to vary the benzylic position, are reported. Relative to the reference 4,5-dimethoxy-2-nitrobenzyl group, several o-nitrobenzyl derivatives exhibit a large and red-shifted one-photon absorption within the near-UV range. Uncaging after one-photon excitation was studied by measuring UV-visible absorption and steady-state fluorescence emission on model caged ethers and esters. In the whole series investigated, the caged substrates were released cleanly upon photolysis. Quantum yields of uncaging after one-photon absorption lie within the 0.1-1 % range. We observed that these drop as the maximum wavelength absorption of the o-nitrobenzyl protecting group is increased. A new method based on fluorescence correlation spectroscopy (FCS) after two-photon excitation was used to measure the action uncaging cross section for two-photon excitation. The series of o-nitrobenzyl caged fluorescent coumarins investigated exhibit values within the 0.1-0.01 Goeppert-Mayer (GM) range. Such results are in line with the low quantum yields of uncaging associated with cross-sections of 1-50 GM for two-photon absorption. Although the cross-sections for one- and two-photon absorption of o-nitrobenzyl photolabile protecting groups can be readily improved, we emphasize the difficulty in enlarging the corresponding action uncaging cross-sections in view of the observed trend of their quantum yield of uncaging.

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Section: Linear Absorption and Emission Propertiesmentioning

confidence: 81%

“…Thus, we considered the approximate correlation function [Eq. (14)] with fewer undetermined constants to fit experimental data:…”

Section: Methodsmentioning

confidence: 99%

“…In the fitting process using Equation (14), N tot was assumed from the concentration used in nc and of the illuminated volume from a preliminary calibration, [56] and only …”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

o‐Nitrobenzyl Photolabile Protecting Groups with Red‐Shifted Absorption: Syntheses and Uncaging Cross‐Sections for One‐ and Two‐Photon Excitation

Aujard

Benbrahim

Gouget

et al. 2006

Chemistry A European J

291

292

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“…[48] Eine dreidimensionale chemische Strukturierung von Aminen in einem Agarose-Hydrogel wurde durch die photolytische Abspaltung des Bhc durch ZweiPhotonen-Anregung realisiert.…”

Section: -Nitroindoline (Ni) Wurden Durch Amit Et Al Mitte Derunclassified

Von Ein‐ zu Zwei‐Photonen‐Sonden: photoaktivierbare Reagentien, Aktuatoren und Photoschalter

et al. 2013

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Molekulare Systeme, die mit Licht “ferngesteuert” werden können, sind von wachsender Bedeutung in der Zellbiologie, der Physiologie und den Neurowissenschaften. Der entscheidende Aspekt hierbei ist die hohe räumliche und zeitliche Präzision, die mit Methoden der Lasermikroskopie erreicht werden kann. Das Verfahren der Zwei‐Photonen‐Anregung hat signifikante Vorzüge bei der Visualisierung biologischer Gewebe, allerdings ist der gezielte Entwurf intelligenter Sonden, die mit der Zellphysiologie kompatibel sind, nicht trivial. Dieser Aufsatz diskutiert die “chemischen” Herausforderungen bei der Entwicklung von Zwei‐Photonen‐Sonden.

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