N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-epsilon-(o-nitroveratryloxycarbonyl)-L-lysine

Description: 2-nitroveratryl (oNv) is a new orthogonal group which is compatible with SPPS protocols and that can be cleaved by photolysis (350 nm) under ambient conditions. See also our product Fmoc-L-Cys(oNv)-OH (FAA3970), where o-nitroveratryl has been used for thiol protection. In order to demonstrate the versatility of this approach, it was applied to the synthesis of a number of model peptides: oxytocin, alpha-conotoxin ImI, and human insulin. References: Synthesis, stability and optimized photolytic cleavage of 4-methoxy-2-nitrobenzyl backbone-protected peptides. Erik C. B. Johnson and Stephen B. H. Kent; Chem. Commun. 2006; 1557-1559. DOI: 10.1039/b600304d Photomodulation of Protein Trans-Splicing Through Backbone Photocaging of the DnaE Split Intein; Luis Berrade, Youngeun Kwon, and Julio A. Camarero; ChemBioChem 2010; 11: 1368 -1372. DOI: 10.1002/cbic.201000157 2-Nitroveratryl as a Photocleavable Thiol-Protecting Group for Directed Disulfide Bond Formation in the Chemical Synthesis of Insulin; Karas J.A., Scanlon D.B., Forbes B.E., Vetter I., Lewis R.J., Gardiner J., Separovic F., Wade J.D., Hossain M.A.; Chem. Eur. J. 2014; 20: 9549-9552. DOI: 10.1002/chem.201403574. Syntheses and kinetic studies of cyclisation-based self-immolative spacers; Steve Huvelle, Ahmed Alouane, Thomas Le Saux, Ludovic Jullien and Frédéric Schmidt; Org. Biomol. Chem. 2017; 15: 3435-3443. DOI: 10.1039/C7OB00121E Self-Immolative Spacers: Kinetic Aspects, Structure-Property Relationships, and Applications; Ahmed Alouane, Raphaël Labruère, Thomas Le Saux, Frédéric Schmidt, and Ludovic Jullien; Angew. Chem. Int. Ed. 2015; 54: 7492-7509. DOI: 10.1002/anie.201500088 Fluorogenic Label for Biomolecular Imaging; Luke D. Lavis, Tzu-Yuan Chao, and Ronald T. Raines; ACS Chem. Biol. 2006; 1(4): 252-260. DOI: 10.1021/cb600132m Prodrug Strategies Based on Intramolecular Cyclization Reactions; Daxian Shan, Michalis G. Nicolaou, Ronald T. Borchardt, and Binghe Wang; J. Pharm. Sci. 1997; 86(7): 765-767. DOI: S0022-3549(97)00069-5 Intramolecular Cyclization Assistance for Fast Degradation of Ornithine-Based Poly(ester amide)s; Caroline de Gracia Lux, Jason Olejniczak, Nadezda Fomina, Mathieu L. Viger, Adah Almutairi; J. Polym. Sci. Part A: Polym. Chem. 2013; 51: 3783-3790. DOI: 10.1002/pola.26788 Design and Synthesis of Photochemically Controllable Restriction Endonuclease BamHI by Manipulating the Salt-Bridge Network in the Dimer Interface; Masayuki Endo, Koji Nakayama, and Tetsuro Majima; J. Org. Chem. 2004; 69: 4292-4298. DOI: 10.1021/jo035774n Development of photolabile caged analogs of endothelin-1; S. Bourgault, M. Le'tourneau, A. Fournier; Peptides 2007; 28: 1074-1082. doi:10.1016/j.peptides.2007.02.013 Total chemical synthesis of photoactivatable proteins for light-controlled manipulation of antigen-antibody interactions; Shan Tang, Zhengpeng Wan, Yiren Gao, Ji-Shen Zheng, Jing Wang, Yan-Yan Si, Xin Chen, Hai Qi, Lei Liu and Wanli Liu; Chem. Sci. 2016; 7: 1891-1895. DOI: 10.1039/c5sc03404c