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Aloc-L-Arg(Pbf)-OH
Chemical name: N-alpha-Allyloxycarbonyl-N'-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine // Synonyms: Aloc-Arg(Pbf)-OH, Alloc-Arg(Pbf)-OH, (S)-2-(allyloxycarbonylamino)-5-(3-(2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-ylsulfonyl)guanidino)pentanoic acid, Alloc-L-Arg(Pbf)-OH
- Product code:AAA2030
- CAS No.:783371-61-9
- Formula:C23H34N4O7S
- Molecular weight:510.6 g/mol
- Purity :min. 98%
- Enantiomeric Purity:min. 99,7%
from $112.50
description
Reported for the synthesis of an Arg analogue of Teixobactin, where L-Arg (linear) replaced the L-allo-enduracididine (cyclic) residue as both of these building blocks are guanidine-based amino acids. The Aloc protecting group is fully compatible with Fmoc/tBu and Boc/Bzl strategies. N-Allyloxycarbonyl (Aloc) are widely used protecting groups, i.e. for amines and amino acids, as they are quantitatively and very rapidly converted to free amino compounds by palladium. The 2,2,4,6,7-pentamethyIdlhydrobenzofuran-5-sulfonyl group (Pbf) can be easily cleaved by trifluoroacetic acid (TFA).
references
Synthesis of a PNA-encoded cysteine protease inhibitor library; F. Debaene, L. Mejias, J. L. Harris, N. Winssinger; Tetrahedron 2004; 60(39): 8677-8690. https://doi.org/10.1016/j.tet.2004.05.107.
Synthesis and Biological Evaluation of a Teixobactin Analogue; Y. E. Jad, G. A. Acosta, T. Naicker, M. Ramtahal, A. El-Faham, T. Govender, H. G. Kruger, B. G. de la Torre, F. Albericio. Org. Lett. 2015; 17(24): 6182-6185. https://doi.org/10.1021/acs.orglett.5b03176.
Preparation of compounds having amino acid residue or peptide residue and process for producing the same; H. Ikeda, M. Tonosaki; PCT Int. Appl. Patent 2006; WO2006115230 A1.
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