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Fmoc-L-Arg(Boc,Bu-NHBoc)-OH
Chemical name: N-alpha-(9-Fluorenylmethyloxycarbonyl)-N'-t-butyloxycarbonyl-N''-(4-t-butyloxycarbonylaminobutyl)carbamoyl-L-arginine // Synonyms: Fmoc-Arg(Boc-NH-butyl)(Boc)-OH, Fmoc-Arg(Boc,Bu-NHBoc)-OH, Fmoc-N-omega-(Boc-aminobutyl)-L-arginine(Boc), (S)-Fmoc-2-amino-5-(N'-Boc-N''(Boc-aminobutyl-guanidino)-pentanoic acid,(S)-18-(((9H-fluoren -9-yl)methoxy)carbonylamino)-13-(tert-butoxycarbon
- Product code:FAA7210
- CAS No.:1872226-95-3
- Formula:C36H50N6O9
- Storage temperature:2-8°C
- Molecular weight:710.82 g/mol
from €225.00
description
An arginine derivative, where the guanidine group is replaced by an amino-functionalized, carbamoylated guanidine group, which can serve for peptide derivatization (conjugation). This labeling strategy was applied to arginine-containing peptide receptor ligands, such as angiotensin II, neurotensin(8−13) and neuropeptide Y mimics, affording tritium and fluorescence labeled peptidic ligands with high receptor affintiy. The carbamoylguanidine group is a chemically stable structure. Its basicity is lower compared to the unsubstituted guanidine group in arginine, but basic enough (pKa ca. 8) to be protonated at physiological pH. Therefore, this modified arginine proved to be a bioisosteric substitute of L-arginine. Incorporation of this building block into peptides has been carried out by SPPS using standard coupling reagents (HBTU/HOBt or PyBOP/HOBt, DIPEA as base, DMF/NMP 80:20 as solvent). The coupling efficiency can be increased by the use of anhydrous solvents and coupling at slightly elevated temperature (35-40 °C). Under these conditions, the use of 3 equivalents of this building block and a prolonged coupling time (16 h) gave the products in high yield.
references
Mimicking of Arginine by Functionalized N(omega)-Carbamoylated Arginine As a New Broadly Applicable Approach to Labeled Bioactive Peptides: High Affinity Angiotensin, Neuropeptide Y, Neuropeptide FF, and Neurotensin Receptor Ligands As Examples; M. Keller, K. K. Kuhn, J. Einsiedel, H. Hubner, S. Biselli, C. Mollereau, D. Wifling, J. Svobodova, G. Bernhardt, C. Cabrele, P. M. Vanderheyden, P. Gmeiner and A. Buschauer; Journal of medicinal chemistry 2016; 59: 1925-45. https://doi.org/10.1021/acs.jmedchem.5b01495
Fluorescence Labeling of Neurotensin(8-13) via Arginine Residues Gives Molecular Tools with High Receptor Affinity; M. Keller, S. A. Mahuroof, V. Hong Yee, J. Carpenter, L. Schindler, T. Littmann, A. Pegoli, H. Hubner, G. Bernhardt, P. Gmeiner and N. D. Holliday; ACS Med Chem Lett 2020; 11: 16-22. https://doi.org/10.1021/acsmedchemlett.9b00462
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