Photolabile Bifunctional Linkers for Light-Triggered Release of Active Molecules
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o-Nitrobenzyl Photolabile Bifunctional Linkers are photolabile protecting groups used to prepare caged compounds, in which the function of an active molecule is masked until it is released by light irradiation, allowing control in a time- and space-selective manner.¹) Three linkers with a photolabile o-nitrobenzyl structure have been used as photolabile bifunctional linkers: 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). The carbonyl groups of 1 and 2 and the hydroxy group of 3 can be used to introduce active molecules that are released by light, while the carboxy group of 1 and the carboxy groups derived from the tert-butyl ester of 2 and 3 can be used to introduce functional molecules. These linkers are used in solid-phase synthesis,²,³) preparation of photolabile polymers⁴) and control of protein activity and fluorescence.⁵)
Related products
- TCI A3678 188891-18-1 4-(4-Acetyl-2-methoxy-5-nitrophenoxy)butanoic Acid
- TCI B6669 1410809-15-2 tert-Butyl 4-(4-Acetyl-2-methoxy-5-nitrophenoxy)butanoate
- TCI B6668 1410809-16-3 tert-Butyl 4-[4-(1-Hydroxyethyl)-2-methoxy-5-nitrophenoxy]butanoate
References
- Photoremovable Protecting Groups in Chemistry and Biology: Reaction Mechanisms and Efficacy. P. Klan et al., Chem. Rev. 2013, 113, 119.
- Model Studies for New o-Nitrobenzyl Photolabile Linkers: Substituent Effects on the Rates of Photochemical Cleavage. C. P. Holmes, J. Org. Chem. 1997, 62, 2370.
- A photolabile carbamate based dual linker analytical construct for facile monitoring of solid phase chemistry. S. C. McKeown et al., Tetrahedron Lett. 1999, 40, 2407.
- Synthesis of Photodegradable Macromers for Conjugation and Release of Bioactive Molecules. D. R. Griffin et al., Biomacromolecules 2013, 14, 1199.
- Simultaneous Triggering of Protein Activity and Fluorescence. J.-P. Pellois, M. E. Hahn, T. W. Muir, J. Am. Chem. Soc. 2004, 126, 7170.
Source
- TCI Product Highlights: www.tcichemicals.com/ID/en/product/tci-topics/ProductHighlights_20241223
- TCI product page A3678: tcichemicals.com/ID/en/p/A3678
For research and laboratory use only, not for human consumption.
