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Chemical name: 4-(Fmoc-amino)-3-Nitro-benzoic acid // Synonyms: 4-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-nitro-benzoic acid
|Molecular weight:||404,37 g/mol|
Typically, 3,4-diaminobenzoid acid (Dbz) is used for the efficient synthesis of peptide thioesters by Fmoc chemistry solid phase peptide synthesis. Optionally, a solubility tag can be attached to the C-terminus. Protection of the free amine is required to prevent over-acylation observed using the typical Dawson reagent. The 4-amino-3-nitrobenzoic acid linker was developed for microwave-assisted synthesis. Dbz(NO2) can easily be converted into the Dbz linker by on-resin reduction with SnCl2 after peptide synthesis.
Eventhough, epimerization of the C-terminal amino acid limits the use of the nitro derivative, it prevents side reactions which occur when Dbz or Dbz(Alloc) linkers are used during microwave-assisted synthesis, e.g. of Gly-rich peptides.
Preparation of Peptide o-Aminoanilides Using a Modified Dawson’s Linker for Microwave-Assisted Peptide Synthesis; S. Tsuda, T. Uemura, M. Mochizuki, H. Nishio, T. Yoshiya; Synlett 2017; 28: 1956-1960. https://doi.org/10.1055/s-0036-1588862.
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