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Fmoc-L-Lys(carbamoyl-OtBu)-OH
Nom chimique: N-alpha-(9-Fluorenylmethoxycarbonyl)-N-epsilon-(t-butoxycarbamoyl)-L-lysine // Synonymes: Fmoc-Lys(carbamoyl-OtBu)-OH, Fmoc-Cit(tBuO)-OH, N-alpha-(9-Fluorenylmethyloxycarbonyl)-N'-t-butoxy)-L-citrulline,N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N6-(t-butoxycarbamoyl)-L-lysine
- n° Art.:FAA8350
- n° CAS:2387846-16-2
- Storage temperature:2-8°C
- Formule:C26H33N3O6
- Masse moléculaire:483,57 g/mol
from 1 350,00 €
description
Histone deacetylases (HDACs), pivotal enzymes in the regulation of gene expression, can be efficiently inhibited by substrate peptidomimetic inhibitors (SPIs), as shown by Jamiesen et al. The inhibiting properties of SPIs stem from the presence of non-natural amino acids able to coordinate the HDAC active site zinc(II). Such amino acids with chelating properties can be obtained by the suitable placement of functional groups with donor properties within their side chain, such as amino, carbonyl, oxyamino or hydroxyl groups. The building blocks Fmoc-Asu(NH-OtBu)-OH (FAA8295), Fmoc-Lys(carbamoyl-OtBu)-OH (FAA8350), Fmoc-HomoArg(OtBu,Pbf)-OH (FAA8355) and Fmoc-L-Orn(Ac,OBz)-OH (FAA4220) are compatible with standard Fmoc/tBu SPPS protocols and represent ready to use efficient tools for the fine-tuning of the chelating properties of peptides.
references
Synthesis of HDAC Substrate Peptidomimetic Inhibitors Using Fmoc Amino Acids Incorporating Zinc-Binding Groups; A. Mahindra, C. J. Millard, I. Black, L. J. Archibald, J. W. R. Schwabe and A. G. Jamieson; Org Lett 2019; 21: 3178-3182. https://doi.org/10.1021/acs.orglett.9b00885
Probing the structure-activity relationship of endogenous histone deacetylase complexes with immobilized peptide-inhibitors; J. Sindlinger, J. Bierlmeier, L. C. Geiger, K. Kramer, I. Finkemeier and D. Schwarzer; J Pept Sci 2016; 22: 352-9. https://doi.org/10.1002/psc.2875
Interrogating Substrate Selectivity and Composition of Endogenous Histone Deacetylase Complexes with Chemical Probes; A. Dose, J. Sindlinger, J. Bierlmeier, A. Bakirbas, K. Schulze-Osthoff, S. Einsele-Scholz, M. Hartl, F. Essmann, I. Finkemeier and D. Schwarzer; Angew Chem Int Ed Engl 2016; 55: 1192-5. https://doi.org/10.1002/anie.201508174
Histone deacetylase (HDAC) 1 and 2 complexes regulate both histone acetylation and crotonylation in vivo; R. D. W. Kelly, A. Chandru, P. J. Watson, Y. Song, M. Blades, N. S. Robertson, A. G. Jamieson, J. W. R. Schwabe and S. M. Cowley; Scientific reports 2018; 8: 14690. https://doi.org/10.1038/s41598-018-32927-9
HDAC inhibitors: a 2013-2017 patent survey; M. Faria Freitas, M. Cuendet and P. Bertrand; Expert Opin Ther Pat 2018; 28: 1-17. https://doi.org/10.1080/13543776.2018.1459568
Fmoc protected (2s)-2-amino-8-[(1,1-dimethylethoxy)amino]-8-oxo-octanoic acid, (s)-2-amino-8-oxononanoic acid and (s)-2-amino-8-oxodecanoic acid for peptide synthesis; A. Jamieson, A. Mahindra, I. Black; 2019; WO2019219938A1.
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