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Chemical Compound Review

CHEMBL115041     4-azidobenzoic acid

Synonyms: AG-G-41097, ACMC-209nl8, ANW-34842, CCG-40396, NSC-80932, ...
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High impact information on p-Azidobenzoic acid

  • These compounds were tested on T1 cytotoxic T lymphocytes (CTLs), which recognize the Plasmodium berghei circumsporzoite peptide 252-260 (SYIPSAEKI) containing photoreactive 4-azidobenzoic acid on Lys(259) in the context of H-2K(d) [1].
  • To elucidate the structural basis of T cell recognition of hapten-modified antigenic peptides, we studied the interaction of the T1 T cell antigen receptor (TCR) with its ligand, the H-2Kd-bound Plasmodium berghei circumsporozoite peptide 252-260 (SYIPSAEKI) containing photoreactive 4-azidobenzoic acid (ABA) on P. berghei circumsporozoite Lys259 [2].
  • The photoreactive insulin derivatives N epsilon B29-(azidobenzoyl)insulin (MAB-insulin) and N alpha A1, N epsilon B29-di(azidobenzoyl)insulin (DAB-insulin) were synthesized by reacting bovine insulin with the N-hydroxysuccinimide ester of 4-azidobenzoic acid [3].

Anatomical context of p-Azidobenzoic acid

  • The Kd-restricted Plasmodium berghei circumsporozoite peptide 253-260 (YIPS-AEKI) was conjugated with iodo-4-azidosalicylic acid at the N terminus and with 4-azidobenzoic acid at the T cell receptor residue Lys-259 [4].


  1. Soluble major histocompatibility complex-peptide octamers with impaired CD8 binding selectively induce Fas-dependent apoptosis. Guillaume, P., Legler, D.F., Boucheron, N., Doucey, M.A., Cerottini, J.C., Luescher, I.F. J. Biol. Chem. (2003) [Pubmed]
  2. T cell recognition of hapten. Anatomy of T cell receptor binding of a H-2kd-associated photoreactive peptide derivative. Kessler, B., Michielin, O., Blanchard, C.L., Apostolou, I., Delarbre, C., Gachelin, G., Grégoire, C., Malissen, B., Cerottini, J.C., Wurm, F., Karplus, M., Luescher, I.F. J. Biol. Chem. (1999) [Pubmed]
  3. Photoaffinity labeling of insulin receptor proteins of liver plasma membrane preparations. Yip, C.C., Yeung, C.W., Moule, M.L. Biochemistry (1980) [Pubmed]
  4. Photoaffinity labeling of the T cell receptor on cloned cytotoxic T lymphocytes by covalent photoreactive ligand. Luescher, I.F., Cerottini, J.C., Romero, P. J. Biol. Chem. (1994) [Pubmed]
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