Photosensitive protection of functional groups

Barton, D. H. R.; Chow, Yuan L.; Cox, A.; Kirby, G. W.

doi:10.1016/s0040-4039(00)70957-9

Cited by 39 publications

(21 citation statements)

References 3 publications

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“…The isolation of benzyl alcohol as the major aromatic fragment was considered to be a proof of heterolytic cleavage or the benzyl-oxygen bond [17,18]. Another type of photosensitive protectirlg group that is removed by photosolvolysis in a nonhydroxylic solvent was introducted by Barton and co-workers [19][20][21]. These authors showed that 2,4-dinitrobenzenesulfenyl esters of carboxylic acids are photolyzed in benzene solutions to yield the free acids in almost quantitative yields.…”

Section: Protecting Groups Removable By Photosolvolysis Reacfionsmentioning

confidence: 99%

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Photosensitive Protecting Groups — A Review

Amit

Zehavi

Patchornik

1974

Israel Journal of Chemistry

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Section: Protecting Groups Removable By Photosolvolysis Reacfionsmentioning

confidence: 99%

“…It was hoped that such esters would be cleaved to phenoxy radicals that would then abstract hydrogens and thus be reduced to phenols. Photolysis of fluorene and xanthene-9-carboxylic esters of 2-naphthol, gave 2-naphthol in 60% yield [19,20].…”

Section: Miscellaneousmentioning

confidence: 99%

Photosensitive Protecting Groups — A Review

Amit

Zehavi

Patchornik

1974

Israel Journal of Chemistry

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“…Thanks to their relevance for applications in biology, PPGs have been widely studied in the past years to investigate cellular functions or for targeted drug delivery . Barltrop and Schofield and Barton et al . were the first to implement PPGs in peptidic synthesis.…”

Section: Introductionmentioning

confidence: 99%

“…[1][2][3] Thanks to their relevance for applications in biology, [4][5][6] PPGs have been widely studied in the past years to investigate cellular functions [7][8][9] or for targeted drug delivery. [10] Barltrop and Schofield [11] and Barton et al [12] were the first to implement PPGs in peptidic synthesis. A benzyloxycarbonyl group was thus used as protecting group for carboxylic acids, and selectively cleaved by light with ideal orthogonality towards standard chemical deprotection.…”

Section: Introductionmentioning

confidence: 99%

Tandem Systems for Two‐Photon Uncaging of Bioactive Molecules

et al. 2019

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Photodeprotection of biological ligands with the combination of photolabile protecting groups (PPGs) and two‐photon (2P) excitation techniques offers the possibility to control physiological phenomena with utmost spatial and temporal precision. Yet, designing PPGs with sufficient 2P photosensitivity still remains challenging. Direct enhancement of the 2P absorption properties usually relies on modifications of the PPG structure, which sometimes results in unpredictable and counterproductive effects on the uncaging quantum yield. In that respect, combining known PPGs with a suitable two‐photon light‐harvesting antenna within a modular architecture offers a promising alternative. In this Minireview, we highlight this versatile strategy, with a discussion of different tandem 2P uncagers, relying on photoinduced electron transfer (PET), triplet‐ energy transfer (TT‐ET), or Förster resonance energy transfer (FRET) sensitization to enhance the 2P sensitivity of PPGs.

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“…Our photolabile stopper 16 was prepared in a 4-step reaction (Scheme 7 The extended nitrobenzene group on 16 should be large enough to prevent DB24C8 from leaving the ammonium guest. However, when exposed to 365 nm ultraviolet light, 16 is photo-activated and runs through a mechanism 42 that kicks the nitrobenzene out as benzaldehyde 17 (Figure 12). With the nitrobenzene group removed, the cyclic host is no longer confined by our photo-labile stopper but the stoppered polymer.…”

Section: Modifying Our Designmentioning

confidence: 99%

The Synthesis of "Smart" Polymers via "Click" Chemistry and Photo-labile stoppers

Wang¹

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Mechanically interlocked polymers can introduce new methods to engineer a polymer's physical properties. As macromolecular switches they contain a wide range of potential applications, such as developing "smart" materials with tunable mechanical properties. Moreover, preparation of poly[n]rotaxanes has been extremely demanding due to synthetic challenges. Here a polymer rotaxane containing a single mechanical bond shared between dibenzo[24]crown8 and ammonium poly(methyl acrylate) was prepared via dynamic host-guest interactions and CuAAC click chemistry. 1 H NMR has been used to show that polymer rotaxane retains general mechanical bond properties such as intramolecular rotation and translation, and reversibility. Photo-labile stoppers were used to increase efficiency of our synthetic route. Photo-stoppered rotaxanes were synthesized and photo-deprotected to show via 1 H NMR that photo-labile stoppers could be used for rotaxane "lengthening". This technology can potentially be applied to improve yields of mechanically interlocked polymers.

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Photosensitive protection of functional groups

Cited by 39 publications

References 3 publications

Photosensitive Protecting Groups — A Review

Photosensitive Protecting Groups — A Review

Tandem Systems for Two‐Photon Uncaging of Bioactive Molecules

The Synthesis of "Smart" Polymers via "Click" Chemistry and Photo-labile stoppers

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