Nvoc is orthogonal to common SPPS conditions, and allows for the selective deprotection of certain lysine epsilon-amino groups for further functionalization or photocaging experiments.

Removal of the Nvoc protecting group by UV light.

See also our product Fmoc-L-Cys(oNv)-OH (FAA3970), where o-nitroveratryl has been used for thiol protection.

→ Order our new booklet on Photochemistry for a comprehensive overview of our photoactivated compounds and their applications.

→ For example, our new Photochemistry booklet describes further applications of the o-nitroveratryl group in drug delivery and photocaging experiments.

References:

• Total chemical synthesis of photoactivatable proteins for light-controlled manipulation of antigen–antibody interactions; S. Tang, Z. Wan, Y. Gao, J.-S. Zheng, J. Wang, Y.-Y. Si, X. Chen, H. Qi, L. Liu and W. Liu; Chemical Science 2016; 7: 1891-1895. doi:10.1039/C5SC03404C
• 2-Nitroveratryl as a Photocleavable Thiol-Protecting Group for Directed Disulfide Bond Formation in the Chemical Synthesis of Insulin; J. A. Karas, D. B. Scanlon, B. E. Forbes, I. Vetter, R. J. Lewis, J. Gardiner, F. Separovic, J. D. Wade and M. A. Hossain; 2014; 20: 9549-9552. doi:doi:10.1002/chem.201403574
• Intramolecular cyclization assistance for fast degradation of ornithine-based poly(ester amide)s; C. de Gracia Lux, J. Olejniczak, N. Fomina, M. L. Viger and A. Almutairi; 2013; 51: 3783-3790. doi:doi:10.1002/pola.26788
• Photomodulation of Protein Trans-Splicing Through Backbone Photocaging of the DnaE Split Intein; L. Berrade, Y. Kwon  and J. A. Camarero; 2010; 11: 1368-1372. doi:doi:10.1002/cbic.201000157
• Synthesis, stability and optimized photolytic cleavage of 4-methoxy-2-nitrobenzyl backbone-protected peptides; E. C. B. Johnson and S. B. H. Kent; Chemical Communications 2006: 1557-1559. doi:10.1039/B600304D
• Design and Synthesis of Photochemically Controllable Restriction Endonuclease BamHI by Manipulating the Salt-Bridge Network in the Dimer Interface; M. Endo, K. Nakayama and T. Majima; The Journal of Organic Chemistry 2004; 69: 4292-4298. doi:10.1021/jo035774n