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Chemical Compound Review

AC1NUTS4     2-amino-3-indol-3-yl-propanoic acid

Synonyms: trp(.), CHEBI:32730, tryptophan radical, 3-(2-amino-2-carboxyethyl)-1H-indol-1-yl
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Disease relevance of tryptophan radical

  • Control experiments established that oligomers that were not complementary to E. coli trp leader RNA did not affect attenuation and that the 15-mer did not reduce termination when the transcript lacked a complementary region [1].
  • In a highly purified DNA-dependent peptide-synthesizing system, synthesis of the di- and tripeptides predicted from the Salmonella typhimurium trp operon leader sequence, fMet-Ala and fMet-Ala-Ala, also was observed [2].
  • Wild-type and translation-defective trp leader templates of E. coli and Serratia marcescens were employed, and pause RNA synthesis and paused complex release (activation) were quantified relative to synthesis of the terminated leader transcript [3].
  • TRAP (trp RNA-binding attenuation protein) is an 11 subunit RNA-binding protein that regulates expression of genes involved in tryptophan metabolism (trp) in Bacillus subtilis in response to changes in intracellular tryptophan concentration [4].
  • Cloning of the trp gene cluster from a tryptophan-hyperproducing strain of Corynebacterium glutamicum: identification of a mutation in the trp leader sequence [5].

Psychiatry related information on tryptophan radical


High impact information on tryptophan radical

  • Recombinantly expressed TrpRS II binds tryptophan (Trp), ATP, and D. radiodurans tRNA(Trp) and catalyzes the formation of 5' adenyl-Trp and tRNA(Trp), with approximately five times less activity than TrpRS I [7].
  • Translation activates the paused transcription complex and restores transcription of the trp operon leader region [3].
  • These findings indicate that the paused trp leader transcription complex resumes transcription when released by ribosome movement over the leader peptide coding region [3].
  • However, distal nucleotide sequences also seem to play a role in modulating termination at trp t [8].
  • In vivo the mutants have 2- to 4-fold increased levels of expression of the trp operon above the level of the trpR parental strain [9].

Chemical compound and disease context of tryptophan radical


Biological context of tryptophan radical

  • Using this dipeptide synthesis system, we demonstrated that translation initiation at the ribosome binding site used for trp leader peptide synthesis was reduced 10-fold when the transcript contained a segment complementary to the ribosome binding site [2].
  • Transcription proceeding past the trp attenuator of this plasmid terminates at this new terminator sequence and results in the production of a approximately 400-nucleotide long read-through transcript [11].
  • We studied the dependence of pausing on hairpin stability by examining mutant trp templates containing base pair substitutions in the region corresponding to the hairpin secondary structure [12].
  • GST-ASA1 cleavage by thrombin, as well as site-directed mutagenesis modifications of the Trp allosteric site, inactivated the recombinant protein [13].
  • The unusual temperature dependence is fitted by a phenomenological two-state model in which the phosphorescence originates primarily from a donor, tryptophan (Trp) 104, and an acceptor, Trp 60, the populations of which are coupled by a thermally activated triplet-triplet energy transfer process [14].

Anatomical context of tryptophan radical


Associations of tryptophan radical with other chemical compounds

  • In fact, transcription of the trp leader region in vitro results in the fomration of a stable termination complex which can be observed on sucrose gradients or by binding to nitrocellulose filters [19].
  • Horse metmyoglobin, which lacks Tyr-151 of the sperm whale protein, forms an oxygen-reactive tryptophanyl radical and also a phenoxyl radical at Tyr-103 [20].
  • The Vmax (45 nmol min-1mg-1), the apparent K(M) for chorismate (180 microM), and the feedback inhibition by Trp (complete inhibition by 10 microM Trp) of the purified fusion product (GST-ASA1) were comparable to anthranilate synthase purified from plants [13].
  • METHODS: The concentration of TRP and the break-down product kynurenine were measured by high-performance liquid chromatography in- and off-season in sera from patients with seasonal allergic rhinitis (n=12) and from clinically asymptomatic atopic patients sensitized to specific aeroallergens (n=12) [15].
  • We found computational evidence suggesting that ferrous NOS is favored in wild-type NOS when compared to the Trp mutant, consistently with the fact that Trp mutants have been shown to accumulate less Fe(+2)-NO dead end species [21].

Gene context of tryptophan radical

  • We constructed plasmid pAtrp46 in which lacZ gene expression is regulated by the attenuator of the Escherichia coli tryptophan (trp) operon [22].
  • Metabolic changes in transgenic Arabidopsis plants expressing the feedback-resistant anthranilate synthase alpha subunit gene OASA1D were investigated with respect to Trp synthesis and effects on secondary metabolism [23].
  • Analysis of attenuation by measurement of trp mRNA synthesis was facilitated by constructing a plasmid (pAD1) containing the rpoC transcription terminator inserted early in trpE [11].
  • Introduction of these rpoB mutations into mutant strains which terminate transcription abnormally at the trp operon attenuator established that the rpoB mutations alter trp operon expression by increasing or decreasing transcription termination at the attenuator [24].
  • We conclude that during transcription of the trp operon RNA polymerase frequently is rejected at a specific site ahead of the first structural gene, trpE [25].

Analytical, diagnostic and therapeutic context of tryptophan radical


  1. Transcription termination at the tryptophan operon attenuator is decreased in vitro by an oligomer complementary to a segment of the leader transcript. Winkler, M.E., Mullis, K., Barnett, J., Stroynowski, I., Yanofsky, C. Proc. Natl. Acad. Sci. U.S.A. (1982) [Pubmed]
  2. In vitro synthesis of the tryptophan operon leader peptides of Escherichia coli, Serratia marcescens, and Salmonella typhimurium. Das, A., Urbanowski, J., Weissbach, H., Nestor, J., Yanofsky, C. Proc. Natl. Acad. Sci. U.S.A. (1983) [Pubmed]
  3. Translation activates the paused transcription complex and restores transcription of the trp operon leader region. Landick, R., Carey, J., Yanofsky, C. Proc. Natl. Acad. Sci. U.S.A. (1985) [Pubmed]
  4. Characterization of a trp RNA-binding attenuation protein (TRAP) mutant with tryptophan independent RNA binding activity. Li, P.T., Gollnick, P. J. Mol. Biol. (2004) [Pubmed]
  5. Cloning of the trp gene cluster from a tryptophan-hyperproducing strain of Corynebacterium glutamicum: identification of a mutation in the trp leader sequence. Herry, D.M., Dunican, L.K. Appl. Environ. Microbiol. (1993) [Pubmed]
  6. Comparative effects of two type I interferons, human IFN-alpha and ovine IFN-tau on indoleamine-2,3-dioxygenase in primary cultures of human macrophages. Maneglier, B., Rogez-Kreuz, C., Spreux-Varoquaux, O., Malleret, B., Thérond, P., Samah, B., Drouet, I., Dormont, D., Advenier, C., Clayette, P. Fundamental & clinical pharmacology (2007) [Pubmed]
  7. An unusual tryptophanyl tRNA synthetase interacts with nitric oxide synthase in Deinococcus radiodurans. Buddha, M.R., Keery, K.M., Crane, B.R. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  8. Tandem termination sites in the tryptophan operon of Escherichia coli. Wu, A.M., Christie, G.E., Platt, T. Proc. Natl. Acad. Sci. U.S.A. (1981) [Pubmed]
  9. Single base-pair alterations in the Escherichia coli trp operon leader region that relieve transcription termination at the trp attenuator. Stauffer, G.V., Zurawski, G., Yanofsky, C. Proc. Natl. Acad. Sci. U.S.A. (1978) [Pubmed]
  10. Translational control of transcription termination at the attenuator of the Escherichia coli tryptophan operon. Zurawski, G., Elseviers, D., Stauffer, G.V., Yanofsky, C. Proc. Natl. Acad. Sci. U.S.A. (1978) [Pubmed]
  11. Regulation of tryptophan operon expression by attenuation in cell-free extracts of Escherichia coli. Das, A., Crawford, I.P., Yanofsky, C. J. Biol. Chem. (1982) [Pubmed]
  12. Stability of an RNA secondary structure affects in vitro transcription pausing in the trp operon leader region. Landick, R., Yanofsky, C. J. Biol. Chem. (1984) [Pubmed]
  13. Functional expression of Arabidopsis thaliana anthranilate synthase subunit I in Escherichia coli. Bernasconi, P., Walters, E.W., Woodworth, A.R., Siehl, D.L., Stone, T.E., Subramanian, M.V. Plant Physiol. (1994) [Pubmed]
  14. Temperature dependence of the phosphorescence quantum yield of various alpha-lactalbumins and of hen egg-white lysozyme. Smith, C.A., Maki, A.H. Biophys. J. (1993) [Pubmed]
  15. Asymptomatic atopy is associated with increased indoleamine 2,3-dioxygenase activity and interleukin-10 production during seasonal allergen exposure. von Bubnoff, D., Fimmers, R., Bogdanow, M., Matz, H., Koch, S., Bieber, T. Clin. Exp. Allergy (2004) [Pubmed]
  16. alpha-Lactalbumin-enriched low-protein infant formulas: a comparison to breast milk feeding. Heine, W., Radke, M., Wutzke, K.D., Peters, E., Kundt, G. Acta Paediatr. (1996) [Pubmed]
  17. Possible role of cytokine-induced tryptophan degradation in anaemia of inflammation. Weiss, G., Schroecksnadel, K., Mattle, V., Winkler, C., Konwalinka, G., Fuchs, D. Eur. J. Haematol. (2004) [Pubmed]
  18. Anthranilic acid-uraemic toxin damaged red cell's membrane. Tankiewicz, A., Pawlak, D., Pawlak, K., Szewc, D., Myśliwiec, M., Buczko, W. International urology and nephrology. (2005) [Pubmed]
  19. The attenuator of the tryptophan operon in E.coli: rho-mediated release of RNA polymerase from a transcription termination complex in vitro. Fuller, R.S., Platt, T. Nucleic Acids Res. (1978) [Pubmed]
  20. Probing the free radicals formed in the metmyoglobin-hydrogen peroxide reaction. Gunther, M.R. Free Radic. Biol. Med. (2004) [Pubmed]
  21. Proximal effects in the modulation of nitric oxide synthase reactivity: a QM-MM study. Fernández, M.L., Martí, M.A., Crespo, A., Estrin, D.A. J. Biol. Inorg. Chem. (2005) [Pubmed]
  22. Modulation of Escherichia coli tryptophan (trp) attenuation by the UGA readthrough process. Kopelowitz, J., Schoulaker-Schwarz, R., Lebanon, A., Engelberg-Kulka, H. Mol. Gen. Genet. (1984) [Pubmed]
  23. Metabolic changes in Arabidopsis thaliana expressing the feedback-resistant anthranilate synthase alpha subunit gene OASA1D. Ishihara, A., Asada, Y., Takahashi, Y., Yabe, N., Komeda, Y., Nishioka, T., Miyagawa, H., Wakasa, K. Phytochemistry (2006) [Pubmed]
  24. Rifampin resistance mutations that alter the efficiency of transcription termination at the tryptophan operon attenuator. Yanofsky, C., Horn, V. J. Bacteriol. (1981) [Pubmed]
  25. Punctuation of transcription in vitro of the tryptophan operon of Escherichia coli. A novel type of control of transcription. Pannekoek, H., Brammar, W.J., Pouwels, P.H. Mol. Gen. Genet. (1975) [Pubmed]
  26. The reaction of oxygen with radicals from oxidation of tryptophan and indole-3-acetic acid. Candeias, L.P., Wardman, P., Mason, R.P. Biophys. Chem. (1997) [Pubmed]
  27. Heat-induced conformational change and increased chaperone activity of lens alpha-crystallin. Das, B.K., Liang, J.J., Chakrabarti, B. Curr. Eye Res. (1997) [Pubmed]
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