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

B6668

tert-Butyl 4-[4-(1-Hydroxyethyl)-2-methoxy-5-nitrophenoxy]butanoate

Related Product Category Page

• Photolabile Protecting Groups

References

• 1) Photoremovable Protecting Groups in Chemistry and Biology: Reaction Mechanisms and Efficacy
  • P. Klán, T. Šolomek, C. G. Bochet, A. Blanc, R. Givens, M. Rubina, V. Popik, A. Kostikov, J. Wirz, Chem. Rev. 2013, 113, 119.
• 2) 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.
• 3) A photolabile carbamate based dual linker analytical construct for facile monitoring of solid phase chemistry: ‘TLC’ for solid phase?
  • S. C. McKeown, S. P. Watson, R. A.E. Carr, P. Marshall, Tetrahedron Lett. 1999, 40, 2407.
• 4) Synthesis of Photodegradable Macromers for Conjugation and Release of Bioactive Molecules
  • D. R. Griffin, J. L. Schlosser, S. F. Lam, T. H. Nguyen, H. D. Maynard, A. M. Kasko, Biomacromolecules 2013, 14, 1199.
• 5) Simultaneous Triggering of Protein Activity and Fluorescence
  • J.-P. Pellois, M. E. Hahn, T. W. Muir, J. Am. Chem. Soc. 2004, 126, 7170.

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