Fmoc-L-Lys(Nvoc)-OH

Published on 04.10.2018

o-Nitroveratryloxycarbonyl (Nvoc) is a photocleavable side chain protecting group for lysine that can be removed by irradiation with UV light (350 nm).

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
Related Products
    1. Fmoc-L-Lys(Nvoc)-OH
      Fmoc-L-Lys(Nvoc)-OH

      Starting at 250,00 €