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o-Nitrobenzyl Photolabile Bifunctional Linkers
Photolabile protecting groups are used to prepare caged compounds, in which the functionalities are controlled by masking the functional groups of the active molecule. By irradiating caged compounds with light, it is possible to control the function of the active molecule in a time- and space-selective manner.1) 4-(4-Acetyl-2-methoxy-5-nitrophenoxy)butanoic acid (1), tert-butyl 4-(4-acetyl-2-methoxy-5-nitrophenoxy)butanoate (2) and tert-butyl 4-[4-(1-hydroxyethyl)-2-methoxy-5-nitrophenoxy]butanoate (3) have a photolabile o-nitrobenzyl structure and have been used as photolabile bifunctional linkers. The carbonyl groups of 1 and 2 and the hydroxy group of 3 can be used to introduce active molecules to be released by light irradiation, and the carboxy group of 1 and the carboxy groups derived from the tert-butyl ester moiety of 2 and 3 can be used to introduce functional molecules, respectively. To be specific, o-nitrobenzyl photolabile linkers are used in a variety of situations, such as solid-phase synthesis,2,3) preparation of photolabile polymers,4) and the control of protein activity and fluorescence.5)
Related Products
- A3678
- 4-(4-Acetyl-2-methoxy-5-nitrophenoxy)butanoic Acid
- B6669
- tert-Butyl 4-(4-Acetyl-2-methoxy-5-nitrophenoxy)butanoate
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References
- 1) Photoremovable Protecting Groups in Chemistry and Biology: Reaction Mechanisms and Efficacy
- 2) Model Studies for New o-Nitrobenzyl Photolabile Linkers: Substituent Effects on the Rates of Photochemical Cleavage
- 3) A photolabile carbamate based dual linker analytical construct for facile monitoring of solid phase chemistry: ‘TLC’ for solid phase?
- 4) Synthesis of Photodegradable Macromers for Conjugation and Release of Bioactive Molecules
- 5) Simultaneous Triggering of Protein Activity and Fluorescence
