Competing pathways for photoremovable protecting groups: the effects of solvent, oxygen and encapsulation

Field, Thomas M.; Peterson, Julie A.; Ma, Chicheng; Jagadesan, Pradeepkumar; Silva, José Paulo da; Rubina, Marina; Ramamurthy, Vaidhyanathan; Givens, Richard S.

doi:10.1039/d0pp00067a

Cited by 7 publications

(4 citation statements)

References 54 publications

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“…In such a case, the phenolic proton could be transferred to the departing diethyl phosphate anion via multiple assisting water molecules. In any event, substrate release rates from pHP show a Bronsted correlation with p K a for various eliminated LG‐H (33).…”

Section: General Mechanistic Aspects Of Leaving Group Releasementioning

confidence: 93%

The Discovery, Development and Demonstration of Three Caged Compounds^†

Steinmetz

Givens

2021

Photochem & Photobiology

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An overview of the history, mechanistic aspects and applications is provided for p-hydroxyphenacyl (pHP) and benzoin photoremovable protecting groups, which release biologically important leaving groups upon photolysis with UV light. Also discussed is (7-diethylaminocoumarin-4-yl)methyl (DEACM), a photoremovable protecting group that absorbs visible light. These are followed by the a-keto amides and naphtho-and benzothiophene-2-carboxanilides as caging groups, which eliminate leaving groups via photochemically produced zwitterionic intermediates. Also covered are amino-1,4benzoquinones, which upon exposure to green and red wavelengths of light photorearrange to an unstable photoproduct that subsequently eliminates leaving groups in aqueous media. Selected examples are given that use these photoremovable protecting (caging) groups for the light-activated release of biologically important substrates under physiological conditions in cells and tissue as practical applications in biology, biochemistry and physiology. These caging groups have found significant applications because their photochemistry is efficient and a single coproduct is formed in addition to the photoreleased substrate.

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Section: General Mechanistic Aspects Of Leaving Group Releasementioning

confidence: 93%

The Discovery, Development and Demonstration of Three Caged Compounds^†

Steinmetz

Givens

2021

Photochem & Photobiology

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“…45 There are currently ongoing efforts to increase the quantum yield of release of phenolic LGs such as the amino acid tyrosine. 46 Extending the already vast application range for pHP further, it is shown here that even multiple simultaneously present pHP-SCN isotopologues can be used, which, in conjunction with VIPER, makes product release on demand from a desired pHP-LG combination feasible. SCN is chosen as the LG for demonstration because it is easily identiable in the IR.…”

Section: Introductionmentioning

confidence: 90%

Choose your leaving group: selective photodeprotection in a mixture of pHP-caged compounds by VIPER excitation

et al. 2023

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“…Firstly, compared with AT, DL-Tyr contains more types of oxygen-containing groups (for example, amino, carboxyl and hydroxyl), and the bonding strength between DL-Tyr and GO should be theoretically better than AT. However, owing to the poor physical and chemical stability of DL-Tyr, it is easy to be photolyzed [21][22][23][24]. As a result, the amino acid components in the membrane will undergo photolysis, which will weaken the bonding strength between GO nanosheets, resulting in cracking, peeling and falling off of the GO membrane.…”

Section: Effect Of Cross-linking Agentsmentioning

confidence: 99%

Effective cross-linking strategy for graphene oxide membrane with high structural stability and enhanced separation performance

Zhang

Yang

et al. 2023

Nanotechnology

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In order to solve the poor structural stability of graphene oxide (GO) membrane, a facile and effective cross-linking technology was employed to create a high-performance GO membrane. Herein, DL-Tyrosine/amidinothiourea and (3-Aminopropyl) triethoxysilane were used to crosslink GO nanosheets and porous alumina substrate, respectively. The group evolution of GO with different cross-linking agents was detected via FTIR. Ultrasonic treatment and soaking experiment were conducted to explore the structural stability of the different membranes. The GO membrane cross-linked with amidinothiourea exhibits exceptional structural stability. Meanwhile, the membrane has superior separation performance, with the pure water flux reaching approximately 109.6 L∙m-2∙h-1∙bar-1. During the treatment of 0.1 g/L NaCl solution, its permeation flux and rejection for NaCl are about 86.8 L∙m-2∙h-1∙bar-1 and 50.8%, respectively. The long-term filtration experiment also demonstrates that the membrane exhibits great operational stability. All these indicate the cross-linking graphene oxide membrane has promising potential applications in water treatment.

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Competing pathways for photoremovable protecting groups: the effects of solvent, oxygen and encapsulation

Abstract: Extending the applications of Photoremovable Protecting Groups (PPGs) to “cage” phenols has generally met with unusually complex PPG byproducts. In this study, we demonstrate that the p–hydroxyphenacyl (pHP) cage for...

Cited by 7 publications

References 54 publications

The Discovery, Development and Demonstration of Three Caged Compounds^†

The Discovery, Development and Demonstration of Three Caged Compounds^†

Choose your leaving group: selective photodeprotection in a mixture of pHP-caged compounds by VIPER excitation

Effective cross-linking strategy for graphene oxide membrane with high structural stability and enhanced separation performance

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Competing pathways for photoremovable protecting groups: the effects of solvent, oxygen and encapsulation

Abstract: Extending the applications of Photoremovable Protecting Groups (PPGs) to “cage” phenols has generally met with unusually complex PPG byproducts. In this study, we demonstrate that the p–hydroxyphenacyl (pHP) cage for...

Cited by 7 publications

References 54 publications

The Discovery, Development and Demonstration of Three Caged Compounds†

The Discovery, Development and Demonstration of Three Caged Compounds†

Choose your leaving group: selective photodeprotection in a mixture of pHP-caged compounds by VIPER excitation

Effective cross-linking strategy for graphene oxide membrane with high structural stability and enhanced separation performance

Contact Info

Product

Resources

About

The Discovery, Development and Demonstration of Three Caged Compounds^†

The Discovery, Development and Demonstration of Three Caged Compounds^†