3-[(9-Fluorenylmethyloxycarbonyl)amino]-4-(aminomethyl)benzoic acid

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. References: 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.