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Fmoc-L-Lys(Nvoc)-OH
Chemical name: N-alpha-(9-Fluorenylmethyloxycarbonyl)-N-epsilon-(o-nitroveratryloxycarbonyl)-L-lysine // Synonyms: Fmoc-Lys(Nvoc)-OH, (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-6-((4,5-dimethoxy-2-nitrobenzyloxy)carbonylamino)hexanoic acid
- Product code:FAA7230
- CAS No.:150571-28-1
- Formula:C31H33N3O10
- Storage temperature:2-8°C
- Molecular weight:607.61 g/mol
from $312.50
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
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All information contained in our webshop is compiled to the best of our knowledge.
Prices and product availability are subject to change and require reconfirmation. Please contact us for further information.
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