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Chemical Compound Review

D-Trp     (2R)-2-amino-3-(1H-indol-3- yl)propanoic acid

Synonyms: D-Tryptophan, D-Trytophane, D-TRYPTOPHANE, H-D-Trp-OH, H-delta-TRP-oh, ...
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Disease relevance of D-Trytophane


High impact information on D-Trytophane


Chemical compound and disease context of D-Trytophane


Biological context of D-Trytophane


Anatomical context of D-Trytophane


Associations of D-Trytophane with other chemical compounds


Gene context of D-Trytophane


Analytical, diagnostic and therapeutic context of D-Trytophane

  • The occurrence of a D-tryptophan residue was confirmed by chemical synthesis and HPLC elution profiles [25].
  • The dog appears to be a reasonable animal model for the human in studies of D-tryptophan metabolism [26].
  • D-Tca-Cys-Tyr-D-Trp-Arg-Thr-Pen-Thr-NH2 ([D-Tca1]CTAP) (where D-Tca is a cyclic D-tryptophan analogue) was synthesized and evaluated in radioligand competition assays, opioid bioassays, and in an antinociceptive assay (the tail-flick test in mice) [27].
  • Ultraviolet resonance Raman spectroscopy demonstrates a difference in the D-tryptophan dihedral angle for the two contryphan-Tx equilibrium conformers [28].


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  2. Effect of D-tryptophan on hemolysin production in Vibrio parahaemolyticus. Cherwonogrodzky, J.W., Skinner, M.A., Clark, A.G. J. Clin. Microbiol. (1984) [Pubmed]
  3. Inversion of D-tryptophan to L-tryptophan and excretory patterns in the rat and chick. Ohara, I., Otsuka, S.I., Yugari, Y., Ariyoshi, S. J. Nutr. (1980) [Pubmed]
  4. Mutagenicities of indole and 30 derivatives after nitrite treatment. Ochiai, M., Wakabayashi, K., Sugimura, T., Nagao, M. Mutat. Res. (1986) [Pubmed]
  5. Solution conformational dynamics of the C-terminal residues in endothelin-1 and some analogues: a time-resolved fluorescence study. Cowley, D.J., Pelton, J.T. Int. J. Pept. Protein Res. (1995) [Pubmed]
  6. Inhibition of tumor cell growth by interferon-gamma is mediated by two distinct mechanisms dependent upon oxygen tension: induction of tryptophan degradation and depletion of intracellular nicotinamide adenine dinucleotide. Aune, T.M., Pogue, S.L. J. Clin. Invest. (1989) [Pubmed]
  7. Identification of a pituitary growth hormone-releasing peptide (GHRP) receptor subtype by photoaffinity labeling. Ong, H., McNicoll, N., Escher, E., Collu, R., Deghenghi, R., Locatelli, V., Ghigo, E., Muccioli, G., Boghen, M., Nilsson, M. Endocrinology (1998) [Pubmed]
  8. Synthesis and structure-activity relationships of 2-substituted D-tryptophan-containing peptidic endothelin receptor antagonists: importance of the C-2 substituent of the D-tryptophan residue for endothelin A and B receptor subtype selectivity. Fukami, T., Yamakawa, T., Niiyama, K., Kojima, H., Amano, Y., Kanda, F., Ozaki, S., Fukuroda, T., Ihara, M., Yano, M., Ishikawa, K. J. Med. Chem. (1996) [Pubmed]
  9. Synthesis and biological evaluation of cholecystokinin analogs in which the Asp-Phe-NH2 moiety has been replaced by a 3-amino-7-phenylheptanoic acid or a 3-amino-6-(phenyloxy)hexanoic acid. Amblard, M., Rodriguez, M., Lignon, M.F., Galas, M.C., Bernad, N., Artis-Noël, A.M., Hauad, L., Laur, J., Califano, J.C., Aumelas, A. J. Med. Chem. (1993) [Pubmed]
  10. Studies on neurokinin antagonists. 1. The design of novel tripeptides possessing the glutaminyl-D-tryptophylphenylalanine sequence as substance P antagonists. Hagiwara, D., Miyake, H., Morimoto, H., Murai, M., Fujii, T., Matsuo, M. J. Med. Chem. (1992) [Pubmed]
  11. Comparison of the nutritive values of L-, DL- and D-tryptophan in the rat and chick. Ohara, I., Otsuka, S.I., Yugari, Y., Ariyoshi, S. J. Nutr. (1980) [Pubmed]
  12. Bioavailable level and source of cysteine determine protein quality of a commercial enteral product: adequacy of tryptophan but deficiency of cysteine for rats fed an enteral product prepared fresh or stored beyond shelf life. Baker, D.H., Han, Y. J. Nutr. (1993) [Pubmed]
  13. Contryphan-Vn: a novel peptide from the venom of the Mediterranean snail Conus ventricosus. Massilia, G.R., Schininà, M.E., Ascenzi, P., Polticelli, F. Biochem. Biophys. Res. Commun. (2001) [Pubmed]
  14. Stereospecific effects of intraduodenal tryptophan on pyloric and duodenal motility in humans. Edelbroek, M., Sun, W.M., Horowitz, M., Dent, J., Smout, A., Akkermans, L. Scand. J. Gastroenterol. (1994) [Pubmed]
  15. Some sweet and bitter tastants stimulate inhibitory pathway of adenylyl cyclase via melatonin and alpha 2-adrenergic receptors in Xenopus laevis melanophores. Zubare-Samuelov, M., Peri, I., Tal, M., Tarshish, M., Spielman, A.I., Naim, M. Am. J. Physiol., Cell Physiol. (2003) [Pubmed]
  16. Investigation of the chemosensory function of amphids of Syngamus trachea using electrophysiological techniques. Riga, E., Perry, R.N., Barrett, J., Johnston, M.R. Parasitology (1995) [Pubmed]
  17. Inhibitors of human renin. Cyclic peptide analogues containing a D-Phe-Lys-D-Trp sequence. Dutta, A.S., Gormley, J.J., McLachlan, P.F., Major, J.S. J. Med. Chem. (1990) [Pubmed]
  18. Is glycine "sweet" to mice? Mouse strain differences in perception of glycine taste. Manita, S., Bachmanov, A.A., Li, X., Beauchamp, G.K., Inoue, M. Chem. Senses (2006) [Pubmed]
  19. A highly selective NK-2 tachykinin receptor antagonist containing D-tryptophan. Rovero, P., Pestellini, V., Maggi, C.A., Patacchini, R., Regoli, D., Giachetti, A. Eur. J. Pharmacol. (1990) [Pubmed]
  20. Tryptophan protects human melanoma cells against gamma-interferon and tumour necrosis factor-alpha: a unifying mechanism of action. Wood, J.M., Ehrke, C., Schallreuter, K.U. Melanoma Res. (1991) [Pubmed]
  21. Absorption of circularly polarized gamma-radiation in L- and D-amino acids. Keszthelyi, L., Vincze, I. Radiation and environmental biophysics. (1975) [Pubmed]
  22. Synthesis and biological activity of NK-2 selective tachykinin antagonists containing D-tryptophan. Rovero, P., Pestellini, V., Patacchini, R., Giuliani, S., Maggi, C.A., Meli, A., Giachetti, A. Peptides (1990) [Pubmed]
  23. Opiate-like naloxone-reversible actions of somatostatin given intracerebrally. Rezek, M., Havlicek, V., Leybin, L., LaBella, F.S., Friesen, H. Can. J. Physiol. Pharmacol. (1978) [Pubmed]
  24. Production of the Kanagawa hemolysin by Vibrio parahaemolyticus in a synthetic medium. Cherwonogrodzky, J.W., Clark, A.G. Infect. Immun. (1982) [Pubmed]
  25. The first gamma-carboxyglutamic acid-containing contryphan. A selective L-type calcium ion channel blocker isolated from the venom of Conus marmoreus. Hansson, K., Ma, X., Eliasson, L., Czerwiec, E., Furie, B., Furie, B.C., Rorsman, P., Stenflo, J. J. Biol. Chem. (2004) [Pubmed]
  26. Metabolism of D- and L-tryptophan in dogs. Triebwasser, K.C., Swan, P.B., Henderson, L.M., Budny, J.A. J. Nutr. (1976) [Pubmed]
  27. Unexpected antinociceptive potency of cyclic [D-Tca1]CTAP: potential for a novel mechanism of action. Horan, P.J., Wild, K.D., Kazmierski, W.M., Ferguson, R., Hruby, V.J., Weber, S.J., Davis, T.P., Fang, L., Knapp, R.J., Yamamura, H.I. Eur. J. Pharmacol. (1993) [Pubmed]
  28. Contryphans from Conus textile venom ducts. Jimenez, E.C., Watkins, M., Juszczak, L.J., Cruz, L.J., Olivera, B.M. Toxicon (2001) [Pubmed]
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