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Fmoc-L-cis-Hyp(NHBoc)-OH
Chemical name: Fmoc-4-(Boc-amino)oxy)-proline (2S,4S) // Synonyms: Fmoc-Pro(4-O-NHBoc)-OH, (2S,4S)-1-(9-fluorenmethyloxycarbonyl)-4-(((tert-butoxycarbonyl)amino)oxy)pyrrolidine-2-carboxylic acid,(2S,4S)-Fmoc-4-(((tert-butoxycarbonyl)amino)oxy)-pyrrolidine-2-carboxy lic acid, Fmoc-4-(((tert-butoxycarbonyl)amino)oxy)
- Product code:FAA8460
- CAS No.:1015426-31-9
- Formula:C25H28N2O7
- Storage temperature:2-8°C
- Molecular weight:468.50 g/mol
from $375.00
description
Aminooxy-containing proline analogues bearing Fmoc/Boc protection suitable for the incorporation into peptides using Fmoc protocols. Deprotection of the aminooxy-function after completion of the peptide synthesis allows for oxime formation through reaction with aldehydes. This allows the post solid-phase synthesis of diverse derivative for structure-activity studies.
references
Protected aminooxyprolines for expedited library synthesis: Application to Tsg101-directed proline-oxime containing peptides; F. Liu, A. G. Stephen, R. J. Fisher, T. R. Burke; Med. Chem. Lett. 2008; 18: 1096-1101. https://doi.org/10.1016/j.bmcl.2007.12.003.
SAR by Oxime-Containing Peptide Libraries: Application to Tsg101 Ligand Optimization; F. Liu, A. G. Stephen, A. A. Waheed, M. J. Aman, E. O. Freed, R. J. Fisher, T. R. Burke; Chembiochem 2008; 9: 2000-2004. https://doi.org/10.1002/cbic.200800281.
Eludication of New Binding Interactions with the Human Tsg101 Protein Using Modified HIV-1 Gag-p6 Derived Peptide Ligands; S.-E. Kim, F. Liu, Y. J. Im, A. G. Stephen, M. J. Fivash, A. A. Waheed, E. O. Freed, R. J. Fisher, J. H. Hurley, T. R. Burke; ACS Med. Chem. Lett. 2011; 2: 337-341. https://doi.org/10.1021/ml1002579.
Identification of High Affinity Polo-like Kinase 1 (Plk1) Polo-box Domain Binding Peptides Using Oxime-Based Diversification; F. Li, J.-E. Park, W.-J. Qian, D. Lim, A. Scharow, T. Berg, M. B. Yaffe, K. S. Lee, T. R. Burke; ACS Chem. Biol. 2012; 7: 805-810. https://doi.org/10.1021/cb200469a.
Cross-Linked Collagen Triple Helices by Oxime Ligation; N. B. Hentzen, L. E. J. Smeenk, J. Witek, S. Riniker, and H. Wennemers; J. Am. Chem. Soc. 2017; 139: 12815-12820. https://doi.org/10.1021/jacs.7b07498.
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