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Fmoc-L-Lys(5-STrt, Boc)-OH
Chemischer Name: (2S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-6-((tert-butoxycarbonyl)amino)-5-(tritylthio)hexanoic acid // Synonyme: Fmoc-Lys(5-STrt, Boc)-OH
- Art-Nr.:FAA9335
- CAS Nr.:1240666-29-8
- Formel:C45H46N2O6S
- Molare Masse:742,93 g/mol
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description
Bicyclic peptides have high potential as next generation pharmaceuticals, e.g., to disrupt the difficult to target interactions between proteins. For controlled cyclization, selective reactivities are required. Our 1,2-aminothiol and 1,3-thiazole building blocks yield the ideal combination for this purpose, and, in addition, are compatible with SPPS. Besides, when used N-terminally, 1,2-aminothiols are useful for connecting peptide fragments by native chemical ligation (NCL).
references
Traceless and Site-Specific Ubiquitination of Recombinant Proteins; S. Virdee, P. B. Kapadnis, T. Elliott, K. Lang, J. Madrzak, D. P. Ngyuen, L. Riechmann, J. W. Chin; J. Am. Chem. Soc. 2011; 133(28): 10708–10711. https://doi.org/10.1021/ja202799r
Chemical synthesis of ubiquitin, ubiquitin-based probes, and diubiquitin; F. El Oualid, R. Merkx, R. Ekkebus, D. S. Hameed, J. J. Smit, A. de Jong, H. Hilkmann, T. K. Sixma, H. Ovaa; Angew Chem Int Ed Engl. 2010; 49(52): 10149-53. https://doi.org/10.1002/anie.201005995
Protecting group variations of δ-mercaptolysine useful in chemical ubiquitylation; M. Haj-Yahya, K. S. A. Kumar, L. A. Erlich, A. Brik; Biopolymers 2010; 94(4): 504-510. https://doi.org/10.1002/bip.21384
Highly efficient and chemoselective peptide ubiquitylation; K. S. A. Kumar, M. Haj-Yahya, D. Olschewski, H. A. Lashuel, A. Brik; Angew Chem Int Ed Engl. 2009; 48(43): 8090-4. https://doi.org/10.1002/anie.200902936
Platform for Orthogonal N-Cysteine-Specific Protein Modification Enabled by Cyclopropenone Reagents; A. Istrate, M. Geeson, C. Navo, B. Sousa, M. Marques, R. Taylor, T. Journeaux, S. Oehler, M. Mortensen, M. Deery, A. Bond, F. Corzana, G. Jiménez-Osés, G. Bernardes; JAmChemSoc. 2022; 144: 10396-10406. https://doi.org/10.1021/jacs.2c02185
Recent advances in N- and C-terminus cysteine protein bioconjugation; R. Spears, V. Chudasama; CurrOpinChemBiol. 2023; 75: 102306. https://doi.org/10.1016/j.cbpa.2023.102306
Biocompatible and Selective Generation of Bicyclic Peptides; S. Ullrich, J. George, A. Coram, R. Morewood, C. Nitsche; AngewChemIntEd. 2022; 61: e202208400. https://doi.org/10.1002/anie.202208400
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