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Fmoc-MeDbz-OH
Chemical name: 3-[(9-Fluorenylmethyloxycarbonyl)amino]-4-(methylamino)benzoic acid // Synonyms: 3-(Fmoc-amino)-4-(methylamino)benzoic acid, Dawson-Linker
- Product code:FAA3166
- CAS No.:1788861-35-7
- Formula:C23H20N2O4
- Storage temperature:2-8°C
- Molecular weight:388.44 g/mol
- Purity :min. 97%
from $107.50
description
MeDbz is a novel linker for the synthesis of peptide thioesters by Fmoc SPPS . After Fmoc removal the resin is being acylated with the first amino acid and then peptide synthesis is carried out. The 4-N-methyl group suppresses the formation of side products on the para-amino moiety. Following chain assembly the resin is being activated by treatment with p-nitrophenyl chloroformate. TFA cleaves the fully deprotected peptide benzimidazolinone which can be converted to a thioester with aryl thiol or used directly in native chemical ligation.
Fmoc-MeDbz is used as a linker in peptide synthesis. It can be cyclysed into a N-acyl-N-methylacylurea using Nitrophenyl chloroformate.
references
Solid-Phase Synthesis of Head to Side-Chain Tyr-Cyclodepsipeptides Through a Cyclative Cleavage From Fmoc-MeDbz/MeNbz-resins; G. A. Acosta, L. Murray, M. Royo, B. G. de la Torre and F. Albericio; Frontiers in Chemistry 2020; 8. https://doi.org/10.3389/fchem.2020.00298
A Reversible Protection Strategy To Improve Fmoc-SPPS of Peptide Thioesters by the N-Acylurea Approach; Santosh K. Mahto, Cecil J. Howard, John C. Shimko, and Jennifer J. Ottesen; ChemBioChem 2011; 12: 2488-2494. DOI: 10.1002/cbic.201100472.
An efficient Fmoc-SPPS approach for the generation of thioester peptide precursors for use in native chemical ligation; Blanco-Canosa, J. B. & Dawson, P. E.; Angew. Chem. Int. Ed. 2008; 47: 6851-6855.
Z. Harpaz, et al.; ChemBioChem 2010; 11: 1232.
B. L. Pentelute, et al., Chem. Biol. 2010; 5: 359.
T. K. Tiefenbrunn, et al.; Pept. Sci. 2010; 94: 405.
Blanco-Canosa, Juan B.; Nardone, Brunello; Albericio, Fernando; Dawson, Philip E. Journal of the American Chemical Society (2015), 137(22), 7197-7209. DOI:10.1021/jacs.5b03504;
Jbara, Muhammad; Maity, Suman Kumar; Seenaiah, Mallikanti; Brik, Ashraf Journal of the American Chemical Society (2016), 138(15), 5069-5075. DOI:10.1021/jacs.5b13580;
Wever, Walter J.; Bogart, Jonathan W.; Bowers, Albert A. Journal of the American Chemical Society (2016), 138(41), 13461-13464. DOI:10.1021/jacs.6b05389; Abdel Monaim, Shimaa A. H.; Acosta, Gerardo A.; Royo, Miriam; El-Faham, Ayman; de la Torre, Beatriz G.; Albericio, Fernando Tetrahedron Letters (2018), 59(18), 1779-1782. DOI:10.1016/j.tetlet.2018.03.084;
Tsuda, Shugo; Mochizuki, Masayoshi; Ishiba, Hiroyuki; Yoshizawa-Kumagaye, Kumiko; Nishio, Hideki; Oishi, Shinya; Yoshiya, Taku Angewandte Chemie, International Edition (2018), 57(8), 2105-2109. DOI:10.1002/anie.201711546.
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All information contained in our webshop is compiled to the best of our knowledge.
Prices and product availability are subject to change and require reconfirmation. Please contact us for further information.
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