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Chemical name: 3-(Fmoc-amino)-4-(Boc-amino)-benzoic acid // Synonyms: 4-tert-Butoxycarbonylamino-3-(9H-fluoren-9-ylmethoxycarbonylamino)-benzoic acid, 3-Fmoc-4-Boc-diaminobenzoic acid
|Molecular weight:||474,51 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. In addition, Boc-protection of the ortho-amine prevents formation of undesired side-products, e.g. benzimidazolinone formation, which might be observed for other types of protecting groups.
Benzimidazolinone-Free Peptide o-Aminoanilides for Chemical Protein Synthesis; J. Mannuthodikayil, S. Singh, A. Biswas, A. Kar, W. Tabassum, P. Vydyam, M. K. Bhattacharyya, and K. Mandal; Org. Lett. 2019; 21: 9040-9044. https://doi.org/10.1021/acs.orglett.9b03440.
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