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Chemical Compound Review

histidine     (2S)-2-amino-3-(3H-imidazol- 4-yl)propanoic...

Synonyms: Istidina, histidina, Histidinum, Polyhistidine, L-Histidin, ...
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Disease relevance of histidine


High impact information on histidine

  • We demonstrate the feasibility of the approach by binding NTA-chromophore conjugates to a representative ligand-gated ion channel and G protein-coupled receptor, each containing a polyhistidine sequence [6].
  • Lactose permease mutants with polyhistidine insertions in cytoplasmic loops IV/V and VI/VII and periplasmic loop VII/VIII retain transport activity and therefore substrate binding, but do not bind enzyme IIAglc, indicating that these regions of lactose permease may be involved in recognition of enzyme IIAglc [7].
  • In plasma membranes from cells expressing the histidine-tagged P2U receptor, but not from cells expressing the wild-type receptor, a single [alpha-32P]BzATP-labeled protein with a molecular mass of 53 kDa was retained on a Ni(2+)-charged Sepharose column, which binds many proteins containing a polyhistidine tag [8].
  • However, after reduction with NaBH4, acid hydrolysis led to a mixture of amino acid derivatives [presumably, isomeric forms of N pi (N tau)-1,4-dihydroxynonanylhistidine] that were indistinguishable from those obtained from insulin and polyhistidine after similar treatment [9].
  • We purified a polyhistidine-tagged form of Prt1p (His-Prt1p) by Ni2+ affinity and gel filtration chromatography and obtained a complex of approximately 600 kDa composed of six polypeptides whose copurification was completely dependent on the polyhistidine tag on His-Prt1p [10].

Chemical compound and disease context of histidine


Biological context of histidine

  • In order to isolate thioredoxin targets related to these phenotypes, we prepared a C35S (Escherichia coli numbering) thioredoxin mutant to stabilize the intermediate disulfide bridged complex and we added a polyhistidine N-terminal extension in order to purify the complex rapidly [16].
  • Transfection experiments demonstrated that polyhistidine-tagged p42 protein, transiently expressed in human U20S cells, was incorporated into endogenous eIF3 [17].
  • The resulting plasmid, pQTy21, was overexpressed in Escherichia coli, and the soluble polyhistidine-tagged protein was purified by metal chelation chromatography [18].
  • A review of published calprotectin amino acid sequences revealed the HEXXH motif of thermolysin-type metalloproteases and an HHH polyhistidine sequence near the C-terminus of the protein's heavy chain [19].
  • We conclude that TSP1 contains a high-affinity binding site for polyhistidine and this is likely to be the molecular basis for the observed binding of TSP1 to histidine-rich glycoprotein [20].

Anatomical context of histidine

  • Expression and characterization of recombinant caveolin. Purification by polyhistidine tagging and cholesterol-dependent incorporation into defined lipid membranes [21].
  • The full-length cDNA for the rat recombinant synaptic vesicle monoamine transporter (rVMAT2) containing a COOH-terminal polyhistidine epitope was engineered into baculovirus DNA for expression in Spodoptera frugiperda (Sf9) cells [22].
  • Analysis of coenzyme Q in polyhistidine-tagged Coq10p purified from mitochondria indicates the presence 0.032-0.034 mol of Q6/mol of protein [23].
  • With the goal of determining the minimum structure of the Na+ channel permeation pathway, we created two stable cell lines expressing the voltage-dependent rat skeletal muscle Na+ channel (micro1) with a polyhistidine tag on the C terminus (muHis) and pore-only micro1 (muPore) channels with S1-S4 in all domains removed [24].
  • Clones NF45 and NF90 with a polyhistidine fusion tag were transiently expressed and processed in the native environment of Jurkat T-cells [25].

Associations of histidine with other chemical compounds


Gene context of histidine

  • We produced polyhistidine-tagged recombinant Rab38 and a polyclonal antibody with a synthetic peptide [34].
  • TCH4 proteins, with and without a polyhistidine tag, that harbor an intact N-terminus are directed to the secretory pathway [35].
  • Protein diagnostic features peculiar to this subfamily include an alternate isoform containing a KGD motif, an elevated basic amino acid content with polyhistidine expansion in the 5'-translated region, and the conservation of 15% core tetrad residues specific to annexin A13 members [36].
  • Recombinant Msi4p with an N-terminal polyhistidine leader was purified on a Ni(2+)-Sepharose column, followed by gel filtration and ion exchange chromatography [37].
  • Activity could also be restored by reconstituting the inactivated membranes with Escherichia coli-expressed, polyhistidine-tagged Leishmania mexicana GPI8 (GPI8-His; L. mexicana GPI8 is a soluble homologue of yeast and mammalian Gpi8p) [38].

Analytical, diagnostic and therapeutic context of histidine


  1. Enteroaggregative Escherichia coli expresses a novel flagellin that causes IL-8 release from intestinal epithelial cells. Steiner, T.S., Nataro, J.P., Poteet-Smith, C.E., Smith, J.A., Guerrant, R.L. J. Clin. Invest. (2000) [Pubmed]
  2. Physical characterization of the procollagen module of human thrombospondin 1 expressed in insect cells. Misenheimer, T.M., Huwiler, K.G., Annis, D.S., Mosher, D.F. J. Biol. Chem. (2000) [Pubmed]
  3. Eukaryotic expression of recombinant biglycan. Post-translational processing and the importance of secondary structure for biological activity. Hocking, A.M., Strugnell, R.A., Ramamurthy, P., McQuillan, D.J. J. Biol. Chem. (1996) [Pubmed]
  4. A two-component signal transduction pathway regulates manganese homeostasis in Synechocystis 6803, a photosynthetic organism. Ogawa, T., Bao, D.H., Katoh, H., Shibata, M., Pakrasi, H.B., Bhattacharyya-Pakrasi, M. J. Biol. Chem. (2002) [Pubmed]
  5. Local and systemic neutralizing antibody responses induced by intranasal immunization with the nontoxic binding domain of toxin A from Clostridium difficile. Ward, S.J., Douce, G., Dougan, G., Wren, B.W. Infect. Immun. (1999) [Pubmed]
  6. Reversible site-selective labeling of membrane proteins in live cells. Guignet, E.G., Hovius, R., Vogel, H. Nat. Biotechnol. (2004) [Pubmed]
  7. Topology of allosteric regulation of lactose permease. Seok, Y.J., Sun, J., Kaback, H.R., Peterkofsky, A. Proc. Natl. Acad. Sci. U.S.A. (1997) [Pubmed]
  8. Functional expression and photoaffinity labeling of a cloned P2U purinergic receptor. Erb, L., Lustig, K.D., Sullivan, D.M., Turner, J.T., Weisman, G.A. Proc. Natl. Acad. Sci. U.S.A. (1993) [Pubmed]
  9. Modification of histidine residues in proteins by reaction with 4-hydroxynonenal. Uchida, K., Stadtman, E.R. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  10. Identification of a translation initiation factor 3 (eIF3) core complex, conserved in yeast and mammals, that interacts with eIF5. Phan, L., Zhang, X., Asano, K., Anderson, J., Vornlocher, H.P., Greenberg, J.R., Qin, J., Hinnebusch, A.G. Mol. Cell. Biol. (1998) [Pubmed]
  11. Phytanoyl-CoA hydroxylase: recognition of 3-methyl-branched acyl-coAs and requirement for GTP or ATP and Mg(2+) in addition to its known hydroxylation cofactors. Croes, K., Foulon, V., Casteels, M., Van Veldhoven, P.P., Mannaerts, G.P. J. Lipid Res. (2000) [Pubmed]
  12. Communication between the nucleotide binding domains of P-glycoprotein occurs via conformational changes that involve residue 508. Gabriel, M.P., Storm, J., Rothnie, A., Taylor, A.M., Linton, K.J., Kerr, I.D., Callaghan, R. Biochemistry (2003) [Pubmed]
  13. A two-dimensional support for selective binding of polyhistidine-tagged proteins: identification of a proliferating cell nuclear antigen point mutant with altered function in vitro. Zaika, A., Mozzherin, D.J., Tan, C.K., Downey, K.M., Fisher, P.A. Anal. Biochem. (1999) [Pubmed]
  14. Expression of a kallikrein-like protease from the snake venom: engineering of autocatalytic site in the fusion protein to facilitate protein refolding. Hung, C.C., Chiou, S.H. Biochem. Biophys. Res. Commun. (2000) [Pubmed]
  15. Cloning, expression, purification and preliminary X-ray crystallographic studies of 2-methylisocitrate lyase from Salmonella typhimurium. Simanshu, D.K., Satheshkumar, P.S., Parthasarathy, S., Savithri, H.S., Murthy, M.R. Acta Crystallogr. D Biol. Crystallogr. (2002) [Pubmed]
  16. In vivo characterization of a thioredoxin h target protein defines a new peroxiredoxin family. Verdoucq, L., Vignols, F., Jacquot, J.P., Chartier, Y., Meyer, Y. J. Biol. Chem. (1999) [Pubmed]
  17. Cloning and characterization of the p42 subunit of mammalian translation initiation factor 3 (eIF3): demonstration that eIF3 interacts with eIF5 in mammalian cells. Bandyopadhyay, A., Maitra, U. Nucleic Acids Res. (1999) [Pubmed]
  18. PCR-based cloning of the full-length Neurospora eukaryotic initiation factor 5A cDNA: polyhistidine-tagging and overexpression for protein affinity binding. Tao, Y., Chen, K.Y. Biochem. J. (1994) [Pubmed]
  19. Histidine-based zinc-binding sequences and the antimicrobial activity of calprotectin. Loomans, H.J., Hahn, B.L., Li, Q.Q., Phadnis, S.H., Sohnle, P.G. J. Infect. Dis. (1998) [Pubmed]
  20. Thrombospondin-1 binds to polyhistidine with high affinity and specificity. Vanguri, V.K., Wang, S., Godyna, S., Ranganathan, S., Liau, G. Biochem. J. (2000) [Pubmed]
  21. Expression and characterization of recombinant caveolin. Purification by polyhistidine tagging and cholesterol-dependent incorporation into defined lipid membranes. Li, S., Song, K.S., Lisanti, M.P. J. Biol. Chem. (1996) [Pubmed]
  22. Peptide mapping of the [125I]Iodoazidoketanserin and [125I]2-N-[(3'-iodo-4'-azidophenyl)propionyl]tetrabenazine binding sites for the synaptic vesicle monoamine transporter. Sievert, M.K., Ruoho, A.E. J. Biol. Chem. (1997) [Pubmed]
  23. The Saccharomyces cerevisiae COQ10 gene encodes a START domain protein required for function of coenzyme Q in respiration. Barros, M.H., Johnson, A., Gin, P., Marbois, B.N., Clarke, C.F., Tzagoloff, A. J. Biol. Chem. (2005) [Pubmed]
  24. A "minimal" sodium channel construct consisting of ligated S5-P-S6 segments forms a toxin-activatable ionophore. Chen, Z., Alcayaga, C., Suarez-Isla, B.A., O'Rourke, B., Tomaselli, G., Marban, E. J. Biol. Chem. (2002) [Pubmed]
  25. Cloning and expression of cyclosporin A- and FK506-sensitive nuclear factor of activated T-cells: NF45 and NF90. Kao, P.N., Chen, L., Brock, G., Ng, J., Kenny, J., Smith, A.J., Corthésy, B. J. Biol. Chem. (1994) [Pubmed]
  26. Human Hepatitis B Viral e Antigen Interacts with Cellular Interleukin-1 Receptor Accessory Protein and Triggers Interleukin-1 Response. Yang, C.Y., Kuo, T.H., Ting, L.P. J. Biol. Chem. (2006) [Pubmed]
  27. Purification and fluorescent labeling of the human serotonin transporter. Rasmussen, S.G., Gether, U. Biochemistry (2005) [Pubmed]
  28. pH-sensitive nanoparticles of poly(amino acid) dodecanoate complexes. General, S., Thünemann, A.F. International journal of pharmaceutics. (2001) [Pubmed]
  29. Immunogenic and antigenic properties of recombinant soluble glycoprotein of rabies virus. Gupta, P.K., Sharma, S., Walunj, S.S., Chaturvedi, V.K., Raut, A.A., Patial, S., Rai, A., Pandey, K.D., Saini, M. Vet. Microbiol. (2005) [Pubmed]
  30. DyP, a unique dye-decolorizing peroxidase, represents a novel heme peroxidase family: ASP171 replaces the distal histidine of classical peroxidases. Sugano, Y., Muramatsu, R., Ichiyanagi, A., Sato, T., Shoda, M. J. Biol. Chem. (2007) [Pubmed]
  31. Functional histidine/nickel hexacyanoferrate nanotube assembly for biosensor applications. Yang, M., Jiang, J., Lu, Y., He, Y., Shen, G., Yu, R. Biomaterials (2007) [Pubmed]
  32. Emerging roles for protein histidine phosphorylation in cellular signal transduction: lessons from the islet beta-cell. Kowluru, A. J. Cell. Mol. Med. (2008) [Pubmed]
  33. Revisiting histidine-dependent acid phosphatases: a distinct group of tyrosine phosphatases. Veeramani, S., Lee, M.S., Lin, M.F. Trends Biochem. Sci. (2009) [Pubmed]
  34. Expression and localization of a novel Rab small G protein (Rab38) in the rat lung. Osanai, K., Iguchi, M., Takahashi, K., Nambu, Y., Sakuma, T., Toga, H., Ohya, N., Shimizu, H., Fisher, J.H., Voelker, D.R. Am. J. Pathol. (2001) [Pubmed]
  35. Co- and/or post-translational modifications are critical for TCH4 XET activity. Campbell, P., Braam, J. Plant J. (1998) [Pubmed]
  36. Comparative genetics and evolution of annexin A13 as the founder gene of vertebrate annexins. Iglesias, J.M., Morgan, R.O., Jenkins, N.A., Copeland, N.G., Gilbert, D.J., Fernandez, M.P. Mol. Biol. Evol. (2002) [Pubmed]
  37. Yeast geranylgeranyltransferase type-II: steady state kinetic studies of the recombinant enzyme. Witter, D.J., Poulter, C.D. Biochemistry (1996) [Pubmed]
  38. Soluble GPI8 restores glycosylphosphatidylinositol anchoring in a trypanosome cell-free system depleted of lumenal endoplasmic reticulum proteins. Sharma, D.K., Hilley, J.D., Bangs, J.D., Coombs, G.H., Mottram, J.C., Menon, A.K. Biochem. J. (2000) [Pubmed]
  39. Mutation avoidance and DNA repair proficiency in Ustilago maydis are differentially lost with progressive truncation of the REC1 gene product. Onel, K., Thelen, M.P., Ferguson, D.O., Bennett, R.L., Holloman, W.K. Mol. Cell. Biol. (1995) [Pubmed]
  40. Electron microscopic evidence for the assembly of soluble pentameric extracellular domains of the nicotinic acetylcholine receptor. Tierney, M.L., Unwin, N. J. Mol. Biol. (2000) [Pubmed]
  41. Reversible immobilization of peptides: surface modification and in situ detection by attenuated total reflection FTIR spectroscopy. Rigler, P., Ulrich, W.P., Hoffmann, P., Mayer, M., Vogel, H. Chemphyschem : a European journal of chemical physics and physical chemistry. (2003) [Pubmed]
  42. Purification, characterization, and identification of novel inhibitors of the beta-ketoacyl-acyl carrier protein synthase III (FabH) from Staphylococcus aureus. He, X., Reynolds, K.A. Antimicrob. Agents Chemother. (2002) [Pubmed]
  43. Serological diagnosis of hantavirus infections by an enzyme-linked immunosorbent assay based on detection of immunoglobulin G and M responses to recombinant nucleocapsid proteins of five viral serotypes. Elgh, F., Lundkvist, A., Alexeyev, O.A., Stenlund, H., Avsic-Zupanc, T., Hjelle, B., Lee, H.W., Smith, K.J., Vainionpää, R., Wiger, D., Wadell, G., Juto, P. J. Clin. Microbiol. (1997) [Pubmed]
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