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Published on 20/04/2021
Fmoc-MeDbz-OH is a linker for the synthesis of peptide thioesters by Fmoc solid phase peptide synthesis. It represents the second generation of the diaminobenzoic acid linker developed by Blanco-Canosa and Dawson. After Fmoc removal the resin is being acylated with the first amino acid and then peptide synthesis is carried out. Notably, the 4-N-methyl group suppresses the formation of side products on the para-amino moiety as the presence of the methyl group makes this position less reactive. Following chain assembly, the resin is being activated by treatment with p-nitrophenyl chloroformate, followed by treatment with a base such as diisopropylethylamine (DIEA) leading to the formation of the N-acyl-N’-methyl-benzimidazolinone (MeNbz) resin. TFA cleaves the fully deprotected peptide benzimidazolinone which can be converted to a thioester with an aryl thiol or used directly in native chemical ligation.
Scheme for the thioester generation by using MeDbz during Fmoc SPPS.
A Reversible Protection Strategy To Improve Fmoc-SPPS of Peptide Thioesters by the N-Acylurea Approach; S. K. Mahto, C. J. Howard, J. C. Shimko, J. J. Ottesen; ChemBioChem 2011; 12: 2488-2494. https://doi.org/10.1002/cbic.201100472.
An efficient Fmoc-SPPS approach for the generation of thioester peptide precursors for use in native chemical ligation; J. B. Blanco-Canosa, P. E. Dawson; Angew. Chem. Int. Ed. Engl. 2008; 47(36): 6851-6855. https://doi.org/10.1002/anie.200705471.
Protein Synthesis Assisted by Native Chemical Ligation at Leucine; Z. Harpa, P. Siman, K. S. A. Kumar, A. Brik; ChemBioChem 2010; 11(9): 1232-1235. https://doi.org/10.1002/cbic.201000168.
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, F. Albericio; Frontiers in Chemistry 2020; 8: xxx. https://doi.org/10.3389/fchem.2020.00298.
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, F. Albericio; Front. Chem. 2020; 8: 298. https://doi.org/10.3389/fchem.2020.00298.
Chemical protein synthesis using a second generation N-acylurea linker for the preparation of peptide-thioester precursors; J. B. Blanco-Canosa, B. Nardone, F. Albericio, P. E. Dawson; J. Am. Chem. Soc. 2015; 137: 7197-7209. https://doi.org/10.1021/jacs.5b03504.
Solid-phase synthesis of homodetic cyclic peptides from Fmoc-MeDbz-resin; S. A. H. A. Monaim, G. A. Acosta, M. Royo, A. El-Faham, B. G. de la Torre, F. Albericio; Tetrahedron Lett. 2018; 59: 1779-1782. https://doi.org/10.1016/j.tetlet.2018.03.084.