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Fmoc-L-Lys(Boc-Cys(Trt))-OH
Chemical name: N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N6-(N-(tert-butoxycarbonyl)-S-trityl-L-cysteinyl)-L-lysine // Synonyms: Fmoc-Lys(Boc-Cys(Trt))-OH
- Product code:FAA9315
- CAS No.:587854-43-1
- Formula:C48H51N3O7S
- Storage temperature:2-8°C
- Molecular weight:814.01 g/mol
from $375.00
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
Improving the stability of thiol–maleimide bioconjugates via the formation of a thiazine structure; I. N. Gober, R. Sharan, M. Villain; J. Pept. Sci. 2023; 29(10): e3495. https://doi.org/10.1002/psc.3495
Biocompatible and Selective Generation of Bicyclic Peptides; S. Ullrich, J. George, A. E. Coram, R. Morewood, C. Nitsche; Angew. Chem. Int. Ed. 2022; 61(43): e202208400. https://doi.org/10.1002/anie.202208400
A biocompatible stapling reaction for in situ generation of constrained peptides; R. Morewood, C. Nitsche; Chem. Sci. 2021; 12: 669-674. https://doi.org/10.1039/D0SC05125J
A Flexible Synthesis of 68Ga-Labeled Carbonic Anhydrase IX (CAIX)-Targeted Molecules via CBT/1,2-Aminothiol Click Reaction; K.-T. Chen, K. Nguyen, C. Ieritano, F. Gao, Y. Seimbille; Molecules 2019; 24(1): 23. https://doi.org/10.3390/molecules24010023
Early-Stage Incorporation Strategy for Regioselective Labeling of Peptides using the 2-Cyanobenzothiazole/1,2-Aminothiol Bioorthogonal Click Reaction; K.-T. Chen, C. Ieritano, Y. Seimbille; ChemistryOpen 2018; 7(3): 256-261. https://doi.org/10.1002/open.201700191
Two bifunctional desferrioxamine chelators for bioorthogonal labeling of biovectors with zirconium-89; F. Gao, C. Ieritano, K.-T. Chen, G. M. Dias, J. Rousseau, F. Benard, Y. Seimbille; Org. Biomol. Chem. 2018; 16: 5102-5106. https://doi.org/10.1039/C8OB01434E
Bifunctional PEGylated exenatide-amylinomimetic hybrids to treat metabolic disorders: an example of long-acting dual hormonal therapeutics; C. Sun, J. L. Trevaskis, C. M. Jodka, S. Neravetla, P. Griffin, K. Xu, Y. Wang, D. G. Parkes, B. Forood, S. S. Ghosh; J Med Chem. 2013; 56(22): 9328-41. https://doi.org/10.1021/jm401418s
Cell permeable ITAM constructs for the modulation of mediator release in mast cells; J. Kuil, M. J. E. Fischer, N. J. de Mol, R. M. J. Liskamp; Org. Biomol. Chem. 2011; 9: 820-833. https://doi.org/10.1039/C0OB00441C
Synthesis and use of a pseudo-cysteine for native chemical ligation; D. A. Alves, D. Esser, R. J. Broadbridge, A. P. G. Beevers, C. P. Chapman, C. E. Winsor, J. R. Betley; J Pept Sci. 2003; 9(4):221-228. https://doi.org/10.1002/psc.448
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
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