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
Molecular weight:388,44 g/mol
Grouped product items
Qty Packing unit Price SKU
500 mg
$116.10
FAA3166.0500
1 g
$180.90
FAA3166.0001
5 g
$648.00
FAA3166.0005
25 g
$2,592.00
FAA3166.0025
Safety Data Sheets
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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