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

Dbz 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. 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.