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T0254 Sigma-Aldrich

L-Tryptophan

reagent grade, ≥98% (HPLC)

Synonym: (S)-2-Amino-3-(3-indolyl)propionic acid, L-α-Amino-3-indolepropionic acid

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Description

Other Notes

Amino acid precursor of serotonin and melatonin

Packaging

1 kg in poly bottle

1, 5, 25, 100, 500 g in poly bottle

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from non-animal source, meets EP, JP, USP testing specifications, suitable for cell culture, 99.0-101.0%

<SC>L</SC>-Tryptophan

PharmaGrade, Ajinomoto, EP, JP, USP, Manufactured under appropriate GMP controls for pharma or biopharmaceutical production, suitable for cell culture

<SC>L</SC>-Tryptophan

BioUltra, ≥99.5% (NT)

Safety & Documentation

Safety Information

WGK Germany 
1
RTECS 
YN6130000

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Certificate of Analysis

Certificate of Origin

Protocols & Articles

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Peer-Reviewed Papers

References

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Chemical genetics reveals a complex functional ground state of neural stem cells Diamandis, P., et. al. Nat. Chem. Biol. 3(5), 268-273, (2007)

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Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species. Denis Fourches et al Chem. Res. Toxicol. 23, 171-83, (2010)

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An expanding range of targets for kynurenine metabolites of tryptophan. Stone TW, Stoy N, and Darlington LG Trends Pharmacol. Sci. 34(2), 136-43, (2013)

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Schizophrenia is primed for an increased expression of depression through activation of immuno-inflammatory, oxidative and nitrosative stress, and tryptophan catabolite pathways. Anderson G, Maes M, and Berk M Prog. Neuropsychopharmacol. Biol. Psychiatry 42, 101-14, (2013)

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Posttranslational biosynthesis of the protein-derived cofactor tryptophan tryptophylquinone. Davidson VL and Wilmot CM Annu. Rev. Biochem. 82, 531-50, (2013)

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Tryptophan biosynthesis protects mycobacteria from CD4 T-cell-mediated killing. Zhang YJ, Reddy MC, Ioerger TR, et al. Cell 155(6), 1296-308, (2013)

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The effect of raising and lowering tryptophan levels on human mood and social behaviour. Young SN Philos. Trans. R. Soc. Lond., B, Biol. Sci. 368(1615), 20110375, (2013)

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Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum. Jing Yuan et al Nat. Chem. Biol. 5, 765-71, (2009)

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Supplementing healthy women with up to 5.0 g/d of L-tryptophan has no adverse effects. Hiratsuka C, Fukuwatari T, Sano M, et al. J. Nutr. 143(6), 859-66, (2013)

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Clinical-grade multipotent adult progenitor cells durably control pathogenic T cell responses in human models of transplantation and autoimmunity. Reading JL, Yang JH, Sabbah S, et al. J. Immunol. 190(9), 4542-52, (2013)

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Prediction and identification of drug interactions with the human ATP-binding cassette transporter multidrug-resistance associated protein 2 (MRP2; ABCC2). Jenny M Pedersen et al J. Med. Chem. 51, 3275-87, (2008)

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Study of the brain serotonergic system with labeled alpha-methyl-L-tryptophan. Diksic M and Young SN J. Neurochem. 78(6), 1185-200, (2001)

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Transport and signaling via the amino acid binding site of the yeast Gap1 amino acid transceptor. Griet Van Zeebroeck et al Nat. Chem. Biol. 5, 45-52, (2009)

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Defining a key receptor-CheA kinase contact and elucidating its function in the membrane-bound bacterial chemosensory array: a disulfide mapping and TAM-IDS Study. Piasta KN, Ulliman CJ, Slivka PF, et al. Biochemistry 52(22), 3866-80, (2013)

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Tryptophan 2,3-dioxygenase (TDO) inhibitors. 3-(2-(pyridyl)ethenyl)indoles as potential anticancer immunomodulators. Dolusic, E.; et al. J. Med. Chem. 54, 5320, (2011)

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Tryptophan metabolism: entering the field of aging and age-related pathologies. van der Goot AT and Nollen EA Trends Mol. Med. 19(6), 336-44, (2013)

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Tryptophan catabolism in cancer: beyond IDO and tryptophan depletion. Platten M, Wick W, and Van den Eynde BJ Cancer Res. 72(21), 5435-40, (2012)

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The niacin required for optimum growth can be synthesized from L-tryptophan in growing mice lacking tryptophan-2,3-dioxygenase. Terakata M, Fukuwatari T, Kadota E, et al. J. Nutr. 143(7), 1046-51, (2013)

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A combined spectroscopic and crystallographic approach to probing drug-human serum albumin interactions. David Buttar et al Bioorg. Med. Chem. 18, 7486-96, (2010)

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Effects and side effects associated with the non-nutritional use of tryptophan by humans. Fernstrom JD J. Nutr. 142(12), 2236S-2244S, (2012)

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Characterization of RimO, a new member of the methylthiotransferase subclass of the radical SAM superfamily. Lee KH, et al. Biochemistry 48(42), 10162-74, (2009)

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Lessons learned regarding symptoms of tryptophan deficiency and excess from animal requirement studies. Moehn S, Pencharz PB, and Ball RO J. Nutr. 142(12), 2231S-2235S, (2012)

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Safety of 5-hydroxy-L-tryptophan. Das YT, Bagchi M, Bagchi D, et al. Toxicol. Lett. 150(1), 111-22, (2004)

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A community-based study on determinants of circulating markers of cellular immune activation and kynurenines: the Hordaland Health Study. Theofylaktopoulou D, Midttun Ø, Ulvik A, et al. Clin. Exp. Immunol. 173(1), 121-30, (2013)

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Labelled alpha-methyl-L-tryptophan as a tracer for the study of the brain serotonergic system. Diksic M J. Psychiatry Neurosci. 26(4), 293-303, (2001)

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Membrane depth-dependent energetic contribution of the tryptophan side chain to the stability of integral membrane proteins. Hong H, Rinehart D, and Tamm LK Biochemistry 52(25), 4413-21, (2013)

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Mechanism of action of puroindoline derived tryptophan-rich antimicrobial peptides. Haney EF, Petersen AP, Lau CK, et al. Biochim. Biophys. Acta 1828(8), 1802-13, (2013)

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A chemical screening approach reveals that indole fluorescence is quenched by pre-fibrillar but not fibrillar amyloid-beta. Ashley A Reinke et al Bioorg. Med. Chem. Lett. 19, 4952-7, (2009)

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[Treatment of depression and sleep disorders. Significance of serotonin and L-tryptophan in pathophysiology and therapy]. Riemann D and Vorderholzer U Fortschr. Med. 116(32), 40-2, (1998)

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Pathogenesis of L-tryptophan eosinophilia myalgia syndrome. Sternberg EM Adv. Exp. Med. Biol. 398, 325-30, (1996)

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Protein structure. Structure and activity of tryptophan-rich TSPO proteins. Guo Y, Kalathur RC, Liu Q, et al. Science 347(6221), 551-5, (2015)

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Metabolite profile analysis reveals association of vitamin B-6 with metabolites related to one-carbon metabolism and tryptophan catabolism but not with biomarkers of inflammation in oral contraceptive users and reveals the effects of oral contraceptives on these processes. Rios-Avila L, Coats B, Chi YY, et al. J. Nutr. 145(1), 87-95, (2015)

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Nesprins anchor kinesin-1 motors to the nucleus to drive nuclear distribution in muscle cells. Wilson MH and Holzbaur EL Development 142(1), 218-28, (2015)

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Differential tolerance of 'pseudo-pathogenic' tryptophan residues in calcium-binding EGF domains of short fibulin proteins. Nguyen A and Hulleman JD Exp. Eye Res. 130, 66-72, (2015)

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Short-term oral atrazine exposure alters the plasma metabolome of male C57BL/6 mice and disrupts α-linolenate, tryptophan, tyrosine and other major metabolic pathways. Lin Z, Roede JR, He C, et al. Toxicology 326, 130-41, (2014)

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Romani & Puccetti reply. Romani L and Puccetti P Nature 514(7523), E18, (2014)

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Tryptophan catabolism is unaffected in chronic granulomatous disease. Maghzal GJ, Winter S, Wurzer B, et al. Nature 514(7523), E16-7, (2014)

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Activation of the umami taste receptor (T1R1/T1R3) initiates the peristaltic reflex and pellet propulsion in the distal colon. Kendig DM, Hurst NR, Bradley ZL, et al. Am. J. Physiol. Gastrointest. Liver Physiol. 307(11), G1100-7, (2014)

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Non-native structure appears in microseconds during the folding of E. coli RNase H. Rosen LE, Kathuria SV, Matthews CR, et al. J. Mol. Biol. 427(2), 443-53, (2015)

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A unified bioinspired "aplysinopsin cascade": total synthesis of (±)-tubastrindole B and related biosynthetic congeners. Skiredj A, Beniddir MA, Joseph D, et al. Org. Lett. 16(19), 4980-3, (2014)

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Clinical significance of tryptophan metabolism in the nontumoral hemisphere in patients with malignant glioma. Kamson DO, Lee TJ, Varadarajan K, et al. J. Nucl. Med. 55(10), 1605-10, (2014)

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Tryptophan oxidation in proteins exposed to thiocyanate-derived oxidants. Bonifay V, Barrett TJ, Pattison DI, et al. Arch. Biochem. Biophys. 564, 1-11, (2014)

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Biosynthesis of the ergot alkaloids. Jakubczyk D, Cheng JZ, and O'Connor SE Nat. Prod. Rep. 31(10), 1328-38, (2014)

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Measuring effects of MDMA (ecstasy) abuse on the rate of cerebral serotonin synthesis. Cumming P J. Neurochem. 131(5), 541-5, (2014)

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Vitamins B2 and B6 as determinants of kynurenines and related markers of interferon-γ-mediated immune activation in the community-based Hordaland Health Study. Theofylaktopoulou D, Ulvik A, Midttun Ø, et al. Br. J. Nutr. 112(7), 1065-72, (2014)

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Inhibition of Escherichia coli tryptophan indole-lyase by tryptophan homologues. Do QT, Nguyen GT, Celis V, et al. Arch. Biochem. Biophys. 560, 20-6, (2014)

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Brain serotonin synthesis in MDMA (ecstasy) polydrug users: an alpha-[(11) C]methyl-l-tryptophan study. Booij L, Soucy JP, Young SN, et al. J. Neurochem. 131(5), 634-44, (2014)

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Soluble CD40-ligand (sCD40L, sCD154) plays an immunosuppressive role via regulatory T cell expansion in HIV infection. Jenabian MA, Patel M, Kema I, et al. Clin. Exp. Immunol. 178(1), 102-11, (2014)

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Large-scale profiling of metabolic dysregulation in ovarian cancer. Ke C, Hou Y, Zhang H, et al. Int. J. Cancer 136(3), 516-26, (2015)

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A simple method to engineer a protein-derived redox cofactor for catalysis. Shin S, Choi M, Williamson HR, et al. Biochim. Biophys. Acta 1837(10), 1595-601, (2014)

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Analysis of the co-operative interaction between the allosterically regulated proteins GK and GKRP using tryptophan fluorescence. Zelent B, Raimondo A, Barrett A, et al. Biochem. J. 459(3), 551-64, (2014)

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[Indoleamine 2, 3-dioxygenase activity during neoadjuvant chemotherapy in patients with breast cancer]. Sakurai K, Fujisaki S, Nagashima S, et al. Gan To Kagaku Ryoho. 40(12), 1578-80, (2013)

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Direct observation of a transient ternary complex during IκBα-mediated dissociation of NF-κB from DNA. Alverdi V, Hetrick B, Joseph S, et al. Proc. Natl. Acad. Sci. U. S. A. 111(1), 225-30, (2014)

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Trp'ing tuberculosis. Russell DG Cell 155(6), 1209-10, (2013)

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Impact of different antipsychotics on cytokines and tryptophan metabolites in stimulated cultures from patients with schizophrenia. Krause D, Weidinger E, Dippel C, et al. Psychiatr. Danub. 25(4), 389-97, (2013)

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[Investigation of fluorescent components of drug "heparin" and its complexing with phenylalanine, tyrosine and tryptophan]. Astakhov SS, Iunusov VM, Sultanbaev MV, et al. Bioorg. Khim. 39(1), 55-60, (2013)

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[Peptide composition of extracts of cryopreserved pigs' and piglets' heart fragments]. Rohoza LA, Diubko TS, Hal'chenko SIe, et al. Ukr. Biokhim. Zh. 85(2), 78-83, (2013)

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[Kynurenines in pathogenesis of endogenous psychiatric disorders]. Shilov IuE and Bezrukov MV Vestn. Ross. Akad. Med. Nauk (1), 35-41, (2013)

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The effect of an NK1 receptor antagonist on blood spinal cord barrier permeability following balloon compression-induced spinal cord injury. Leonard AV and Vink R Acta Neurochir. Suppl. 118, 303-6, (2013)

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Persistent infectious diseases say - IDO. Role of indoleamine-2,3-dioxygenase in disease pathogenesis and implications for therapy. Barth H and Raghuraman S Crit. Rev. Microbiol 40(4), 360-8, (2014)

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[Eosinophilia myalgia syndrome (EMS) caused by L-tryptophan product and toxic oil syndrome (TOS) caused by denatured rape-seed oil]. Maitani T and Saitoh H Shokuhin Eiseigaku Zasshi 50(6), 279-91, (2009)

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[L-tryptophan-induced eosinophilia-myalgia syndrome, Chinese restaurant syndrome]. Terao T, Hori H, and Nakamura J Ryoikibetsu. Shokogun. Shirizu. (27 Pt 2), 650-3, (1999)

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Alpha[C-11]methyl-L-tryptophan PET maps brain serotonin synthesis and kynurenine pathway metabolism. Chugani DC and Muzik O J. Cereb. Blood Flow Metab. 20(1), 2-9, (2000)

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Serotonin and aversive Pavlovian control of instrumental behavior in humans. Geurts DE, Huys QJ, den Ouden HE, et al. J. Neurosci. 33(48), 18932-9, (2013)

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Macimorelin (AEZS-130)-stimulated growth hormone (GH) test: validation of a novel oral stimulation test for the diagnosis of adult GH deficiency. Garcia JM, Swerdloff R, Wang C, et al. J. Clin. Endocrinol. Metab. 98(6), 2422-9, (2013)

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Schizophrenia: linking prenatal infection to cytokines, the tryptophan catabolite (TRYCAT) pathway, NMDA receptor hypofunction, neurodevelopment and neuroprogression. Anderson G and Maes M Prog. Neuropsychopharmacol. Biol. Psychiatry 42, 5-19, (2013)

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Inflammation-related disorders in the tryptophan catabolite pathway in depression and somatization. Anderson G, Maes M, and Berk M Adv. Protein Chem. Struct. Biol. 88, 27-48, (2012)

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Carbonic anhydrase activators: activation of the archaeal beta-class (Cab) and gamma-class (Cam) carbonic anhydrases with amino acids and amines. Alessio Innocenti et al Bioorg. Med. Chem. Lett. 18, 6194-8, (2008)

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Oxidation of L-tryptophan in biology: a comparison between tryptophan 2,3-dioxygenase and indoleamine 2,3-dioxygenase. Rafice SA, Chauhan N, Efimov I, et al. Biochem. Soc. Trans. 37(Pt 2), 408-12, (2009)

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Carbonic anhydrase activators: activation of the human isoforms VII (cytosolic) and XIV (transmembrane) with amino acids and amines. Daniela Vullo et al Bioorg. Med. Chem. Lett. 17, 4107-12, (2007)

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Cell death of gamma interferon-stimulated human fibroblasts upon Toxoplasma gondii infection induces early parasite egress and limits parasite replication. Niedelman W, Sprokholt JK, Clough B, et al. Infect. Immun. 81(12), 4341-9, (2013)

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Evolutionary and mechanistic insights into substrate and product accommodation of CTP:phosphocholine cytidylyltransferase from Plasmodium falciparum. Nagy GN, Marton L, Krámos B, et al. FEBS J. 280(13), 3132-48, (2013)

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Calmatives for the excitable horse: a review of L-tryptophan. Grimmett A and Sillence MN Vet. J. 170(1), 24-32, (2005)

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Full implementation of the genetic code by tryptophanyl-tRNA synthetase requires intermodular coupling. Li L and Carter CW J. Biol. Chem. 288(48), 34736-45, (2013)

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Insulin resistance and dysregulation of tryptophan-kynurenine and kynurenine-nicotinamide adenine dinucleotide metabolic pathways. Oxenkrug G Mol. Neurobiol. 48(2), 294-301, (2013)

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Biochemical and medical aspects of the indoleamine 2,3-dioxygenase-initiated L-tryptophan metabolism. Takikawa O Biochem. Biophys. Res. Commun. 338(1), 12-9, (2005)

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Towards bacterial strains overproducing L-tryptophan and other aromatics by metabolic engineering. Ikeda M Appl. Microbiol. Biotechnol. 69(6), 615-26, (2006)

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Novel nutritional treatment for manic and psychotic disorders: a review of tryptophan and tyrosine depletion studies and the potential of protein-based formulations using glycomacropeptide. Badawy A Psychopharmacology 228(3), 347-58, (2013)

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A Trp199Glu MauG variant reveals a role for Trp199 interactions with pre-methylamine dehydrogenase during tryptophan tryptophylquinone biosynthesis. Abu Tarboush N, Jensen LM, Wilmot CM, et al. FEBS Lett. 587(12), 1736-41, (2013)

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Substrate promiscuity of the cyclic dipeptide prenyltransferases from Aspergillus fumigatus ( section sign). Huixi Zou et al J. Nat. Prod. 72, 44-52, (2009)

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Carbonic anhydrase activators: activation of the human tumor-associated isozymes IX and XII with amino acids and amines. Silvia Pastorekova et al Bioorg. Med. Chem. 16, 3530-6, (2008)

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α-[¹¹C]-methyl-L-tryptophan PET for tracer localization of epileptogenic brain regions: clinical studies. Kumar A, Asano E, and Chugani HT Biomark. Med. 5(5), 577-84, (2011)

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α-methyl-L-tryptophan: mechanisms for tracer localization of epileptogenic brain regions. Chugani DC Biomark. Med. 5(5), 567-75, (2011)

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Alpha-methyl-L-tryptophan as a tracer to study brain serotonergic system. Diksic M and Grdisa M Neurochem. Res. 20(11), 1353-60, (1995)

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Tailoring reactions catalyzed by heme-dependent enzymes: spectroscopic characterization of the L-tryptophan-nitrating cytochrome P450 TxtE. Barry SM and Challis GL Meth. Enzymol. 516, 171-94, (2012)

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Femtosecond dynamics of short-range protein electron transfer in flavodoxin. He TF, Guo L, Guo X, et al. Biochemistry 52(51), 9120-8, (2013)

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Homotropic cooperativity from the activation pathway of the allosteric ligand-responsive regulatory trp RNA-binding attenuation protein. Kleckner IR, McElroy CA, Kuzmic P, et al. Biochemistry 52(49), 8855-65, (2013)

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Targeted deletion of kynurenine 3-monooxygenase in mice: a new tool for studying kynurenine pathway metabolism in periphery and brain. Giorgini F, Huang SY, Sathyasaikumar KV, et al. J. Biol. Chem. 288(51), 36554-66, (2013)

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Carbonic anhydrase activators: activation of isozyme XIII with amino acids and amines. Seppo Parkkila et al Bioorg. Med. Chem. Lett. 16, 3955-9, (2006)

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Effects of L-tryptophan on indoleamines and catecholamines in discrete brain regions of wild type and Lurcher mutant mice. Reader, T.A., et al. Neurochem. Res. 24, 1125, (1999)

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A tRNA-dependent two-enzyme pathway for the generation of singly and doubly methylated ditryptophan 2,5-diketopiperazines. Giessen TW, von Tesmar AM, and Marahiel MA Biochemistry 52(24), 4274-83, (2013)

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Positron emission tomography with α-[11C]methyl-L-tryptophan in tuberous sclerosis complex-related epilepsy. Rubí S, Costes N, Heckemann RA, et al. Epilepsia 54(12), 2143-50, (2013)

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Development of new indole-derived neuroprotective agents. Rafat M Mohareb et al Bioorg. Med. Chem. 19, 2966-74, (2011)

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Carbonic anhydrase activators: an activation study of the human mitochondrial isoforms VA and VB with amino acids and amines. Daniela Vullo et al Bioorg. Med. Chem. Lett. 17, 1336-40, (2007)

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Structural insight into the inhibition of human kynurenine aminotransferase I/glutamine transaminase K. Qian Han et al J. Med. Chem. 52, 2786-93, (2009)

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Carbonic anhydrase activators. The first activation study of a coral secretory isoform with amino acids and amines. Anthony Bertucci et al Bioorg. Med. Chem. 18, 2300-3, (2010)

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Design and synthesis of selective inhibitors of placental alkaline phosphatase. Lanier, M., et al. Bioorg. Med. Chem. 18, 573-9, (2010)

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Model of tryptophan metabolism, readily scalable using tissue-specific gene expression data. Stavrum AK, Heiland I, Schuster S, et al. J. Biol. Chem. 288(48), 34555-66, (2013)

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Mechanisms of tryptophan and tyrosine hydroxylase. Roberts KM and Fitzpatrick PF IUBMB Life 65(4), 350-7, (2013)

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Remarkable role of indoleamine 2,3-dioxygenase and tryptophan metabolites in infectious diseases: potential role in macrophage-mediated inflammatory diseases. Murakami Y, Hoshi M, Imamura Y, et al. Mediators Inflamm. 2013, 391984, (2013)

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Carbonic anhydrase activators: kinetic and X-ray crystallographic study for the interaction of D- and L-tryptophan with the mammalian isoforms I-XIV. Claudia Temperini et al Bioorg. Med. Chem. 16, 8373-8, (2008)

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Structure of the cyanobacterial phytochrome 2 photosensor implies a tryptophan switch for phytochrome signaling. Anders K, Daminelli-Widany G, Mroginski MA, et al. J. Biol. Chem. 288(50), 35714-25, (2013)

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Carbonic anhydrase activators: activation of the beta-carbonic anhydrase Nce103 from the yeast Saccharomyces cerevisiae with amines and amino acids. Semra Isik et al Bioorg. Med. Chem. Lett. 19, 1662-5, (2009)

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Indoleamine 2,3 dioxygenase contributes to transferable tolerance in rat red blood cell inducible model of experimental autoimmune haemolytic anaemia. Dahal LN, Hall LS, Barker RN, et al. Clin. Exp. Immunol. 173(1), 58-66, (2013)

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Influence of melatonin and its precursor L-tryptophan on Th1 dependent contact hypersensitivity. Majewska M, Zajac K, Zemelka M, et al. J. Physiol. Pharmacol. 58 Suppl 6, 125-32, (2007)

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Carbonic anhydrase activators: the first activation study of the human secretory isoform VI with amino acids and amines. Isao Nishimori et al Bioorg. Med. Chem. 15, 5351-7, (2007)

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Synthesis, kinetic studies and pharmacological evaluation of mutual azo prodrugs of 5-aminosalicylic acid for colon-specific drug delivery in inflammatory bowel disease. Suneela S Dhaneshwar et al Eur. J. Med. Chem. 44, 3922-9, (2009)

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Colon-specific mutual amide prodrugs of 4-aminosalicylic acid for their mitigating effect on experimental colitis in rats. Suneela S Dhaneshwar et al Eur. J. Med. Chem. 44, 131-42, (2009)

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Epidemiology of potential association between L-tryptophan ingestion and eosinophilia-myalgia syndrome. Daniels SR, Hudson JI, and Horwitz RI J. Clin. Epidemiol. 48(12), 1413-27; discussion 1429-40, (1995)

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Molecular mechanism for differential recognition of membrane phosphatidylserine by the immune regulatory receptor Tim4. Tietjen GT, Gong Z, Chen CH, et al. Proc. Natl. Acad. Sci. U. S. A. 111(15), E1463-72, (2014)

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On the mechanism of photoinduced dimer dissociation in the plant UVR8 photoreceptor. Voityuk AA, Marcus RA, and Michel-Beyerle ME Proc. Natl. Acad. Sci. U. S. A. 111(14), 5219-24, (2014)

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Kinetic evidence for a two-stage mechanism of protein denaturation by guanidinium chloride. Jha SK and Marqusee S Proc. Natl. Acad. Sci. U. S. A. 111(13), 4856-61, (2014)

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The kynurenine pathway of tryptophan catabolism, CD4+ T-cell recovery, and mortality among HIV-infected Ugandans initiating antiretroviral therapy. Byakwaga H, Boum Y, Huang Y, et al. J. Infect. Dis. 210(3), 383-91, (2014)

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Serotonin metabolites in the cerebrospinal fluid in sudden infant death syndrome. Rognum IJ, Tran H, Haas EA, et al. J. Neuropathol. Exp. Neurol. 73(2), 115-22, (2014)

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Histidine decarboxylase deficiency causes tourette syndrome: parallel findings in humans and mice. Castellan Baldan L, Williams KA, Gallezot JD, et al. Neuron 81(1), 77-90, (2014)

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Reversal of the Kynurenine pathway of tryptophan catabolism may improve depression in ART-treated HIV-infected Ugandans. Martinez P, Tsai AC, Muzoora C, et al. J. Acquir. Immune Defic. Syndr. 65(4), 456-62, (2014)

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Trp replacements for tightly interacting Gly-Gly pairs in LacY stabilize an outward-facing conformation. Smirnova I, Kasho V, Sugihara J, et al. Proc. Natl. Acad. Sci. U. S. A. 110(22), 8876-81, (2013)

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Inhibition of indoleamine 2,3-dioxygenase enhances the T-cell response to influenza virus infection. Fox JM, Sage LK, Huang L, et al. J. Gen. Virol. 94(Pt 7), 1451-61, (2013)

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Carbonic anhydrase activators: Activation of the beta-carbonic anhydrase from the pathogenic yeast Candida glabrata with amines and amino acids. Alessio Innocenti et al Bioorg. Med. Chem. Lett. 20, 1701-4, (2010)

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Competition between tryptophan fluorescence and electron transfer during unfolding of the villin headpiece. Parson WW Biochemistry 53(28), 4503-9, (2014)

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A review of the literature on common CYP17A1 mutations in adults with 17-hydroxylase/17,20-lyase deficiency, a case series of such mutations among Koreans and functional characteristics of a novel mutation. Kim YM, Kang M, Choi JH, et al. Metabolism 63(1), 42-9, (2014)

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Antioxidant activity of unexplored indole derivatives: synthesis and screening. Mónica S Estevão et al Eur. J. Med. Chem. 45, 4869-78, (2010)

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An aromatic residue switch in enhancer-dependent bacterial RNA polymerase controls transcription intermediate complex activity. Wiesler SC, Weinzierl RO, and Buck M Nucleic Acids Res. 41(11), 5874-86, (2013)

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Tryptophan-mediated charge-resonance stabilization in the bis-Fe(IV) redox state of MauG. Geng J, Dornevil K, Davidson VL, et al. Proc. Natl. Acad. Sci. U. S. A. 110(24), 9639-44, (2013)

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Carbonic anhydrase activators: Activation of the human cytosolic isozyme III and membrane-associated isoform IV with amino acids and amines. Daniela Vullo et al Bioorg. Med. Chem. Lett. 18, 4303-7, (2008)

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Carbonic anhydrase activators: activation of the beta-carbonic anhydrases from the pathogenic fungi Candida albicans and Cryptococcus neoformans with amines and amino acids. Alessio Innocenti et al Bioorg. Med. Chem. 18, 1034-7, (2010)

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Melatonin and dopamine as biomarkers to optimize treatment in phenylketonuria: effects of tryptophan and tyrosine supplementation. Yano S, Moseley K, and Azen C J. Pediatr. 165(1), 184-189.e1, (2014)

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The tryptophan synthase β-subunit paralogs TrpB1 and TrpB2 in Thermococcus kodakarensis are both involved in tryptophan biosynthesis and indole salvage. Hiyama T, Sato T, Imanaka T, et al. FEBS J. 281(14), 3113-25, (2014)

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Relative domain folding and stability of a membrane transport protein. Harris NJ, Findlay HE, Simms J, et al. J. Mol. Biol. 426(8), 1812-25, (2014)

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Iron(IV)hydroxide pK(a) and the role of thiolate ligation in C-H bond activation by cytochrome P450. Yosca TH, Rittle J, Krest CM, et al. Science 342(6160), 825-9, (2013)

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Glutathione and tryptophan metabolism are required for Arabidopsis immunity during the hypersensitive response to hemibiotrophs. Hiruma K, Fukunaga S, Bednarek P, et al. Proc. Natl. Acad. Sci. U. S. A. 110(23), 9589-94, (2013)

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Redesign of MST enzymes to target lyase activity instead promotes mutase and dehydratase activities. Meneely KM, Luo Q, and Lamb AL Arch. Biochem. Biophys. 539(1), 70-80, (2013)

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Microbiome-derived tryptophan metabolites and their aryl hydrocarbon receptor-dependent agonist and antagonist activities. Jin UH, Lee SO, Sridharan G, et al. Mol. Pharmacol. 85(5), 777-88, (2014)

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Kynurenine 3-monooxygenase mediates inhibition of Th17 differentiation via catabolism of endogenous aryl hydrocarbon receptor ligands. Stephens GL, Wang Q, Swerdlow B, et al. Eur. J. Immunol. 43(7), 1727-34, (2013)

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Inhibitor selectivity between aldo-keto reductase superfamily members AKR1B10 and AKR1B1: role of Trp112 (Trp111). Zhang L, Zhang H, Zhao Y, et al. FEBS Lett. 587(22), 3681-6, (2013)

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Mutation of Trp(93) of MauG to tyrosine causes loss of bound Ca(2+) and alters the kinetic mechanism of tryptophan tryptophylquinone cofactor biosynthesis. Shin S, Feng M, and Davidson VL Biochem. J. 456(1), 129-37, (2013)

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Carbonic anhydrase activators. Activation of the membrane-associated isoform XV with amino acids and amines. Alessio Innocenti et al Bioorg. Med. Chem. Lett. 19, 3430-3, (2009)

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Effects of dietary tryptophan on protein metabolism and related gene expression in Yangzhou goslings under different feeding regimens. Pan X, Wei Z, Wang H, et al. Poult. Sci. 92(12), 3196-204, (2013)

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[(11)C]5-HTP and microPET are not suitable for pharmacodynamic studies in the rodent brain. Visser AK, Ramakrishnan NK, Willemsen AT, et al. J. Cereb. Blood Flow Metab. 34(1), 118-25, (2014)

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A urinary metabonomics study on biochemical changes in yeast-induced pyrexia rats: a new approach to elucidating the biochemical basis of the febrile response. Gao X, Guo M, Zhao B, et al. Chem. Biol. Interact. 204(1), 39-48, (2013)

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Spectrophotometric determination of drugs with iodine. Karuna T, et al. J. Sci. Ind. Res. 65(10), 808, (2006)

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Characterization of amyloid formation by glucagon-like peptides: role of basic residues in heparin-mediated aggregation. Jha NN, Anoop A, Ranganathan S, et al. Biochemistry 52(49), 8800-10, (2013)

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Structural and functional implications of the yeast high-affinity tryptophan permease Tat2. Kanda N and Abe F Biochemistry 52(25), 4296-307, (2013)

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Flexibility of cold- and heat-adapted subtilisin-like serine proteinases evaluated with fluorescence quenching and molecular dynamics. Sigtryggsdóttir AR, Papaleo E, Thorbjarnardóttir SH, et al. Biochim. Biophys. Acta 1844(4), 705-12, (2014)

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Interferon (IFN)-γ-mediated inflammation and the kynurenine pathway in relation to bone mineral density: the Hordaland Health Study. Apalset EM, Gjesdal CG, Ueland PM, et al. Clin. Exp. Immunol. 176(3), 452-60, (2014)

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Plasma L-tryptophan depletion and aggression. Dougherty DM, Moeller FG, Bjork JM, et al. Adv. Exp. Med. Biol. 467, 57-65, (1999)

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Importance of L-tryptophan metabolism in trypanosomiasis. Vincendeau P, Lesthelle S, Bertazzo A, et al. Adv. Exp. Med. Biol. 467, 525-31, (1999)

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Evolution to a chronic disease niche correlates with increased sensitivity to tryptophan availability for the obligate intracellular bacterium Chlamydia pneumoniae. Huston WM, Barker CJ, Chacko A, et al. J. Bacteriol. 196(11), 1915-24, (2014)

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[Immune modulation by tryptophan metabolism: relevance for autoimmune and tumor diseases]. Platten M, Wick W, and Opitz C Dtsch. Med. Wochenschr. 138(28-29), 1478-82, (2013)

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[New developments on the serotonin hypothesis of depression: shunt of tryptophan]. Marazziti D, Baroni S, Picchetti M, et al. Riv. Psichiatr. 48(1), 23-34, (2013)

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Role of decreased plasma tryptophan in memory deficits observed in type-I diabetes. Ahmad S, Tabassum S, and Haider S J. Pak. Med. Assoc. 63(1), 65-8, (2013)

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The C-glycosyltransferase IroB from pathogenic Escherichia coli: identification of residues required for efficient catalysis. Foshag D, Campbell C, and Pawelek PD Biochim. Biophys. Acta 1844(9), 1619-30, (2014)

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Equilibrium folding of pro-HlyA from Escherichia coli reveals a stable calcium ion dependent folding intermediate. Thomas S, Bakkes PJ, Smits SH, et al. Biochim. Biophys. Acta 1844(9), 1500-10, (2014)

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Lipid binding specificity of bovine α-lactalbumin: a multidimensional approach. Chaudhuri A and Chattopadhyay A Biochim. Biophys. Acta 1838(8), 2078-86, (2014)

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Effect of tryptophan supplementation on diet-induced non-alcoholic fatty liver disease in mice. Ritze Y, Bárdos G, Hubert A, et al. Br. J. Nutr. 112(1), 1-7, (2014)

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Single tryptophan mutants of FtsZ: nucleotide binding/exchange and conformational transitions. Montecinos-Franjola F, James NG, Concha-Marambio L, et al. Biochim. Biophys. Acta 1844(7), 1193-200, (2014)

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Enhanced catalytic site thermal stability of cold-adapted esterase EstK by a W208Y mutation. Boyineni J, Kim J, Kang BS, et al. Biochim. Biophys. Acta 1844(6), 1076-82, (2014)

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The N-terminal domain tethers the voltage-gated calcium channel β2e-subunit to the plasma membrane via electrostatic and hydrophobic interactions. Miranda-Laferte E, Ewers D, Guzman RE, et al. J. Biol. Chem. 289(15), 10387-98, (2014)

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Heme-dependent dioxygenases in tryptophan oxidation. Geng J and Liu A Arch. Biochem. Biophys. 544, 18-26, (2014)

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Importance of indole N-H hydrogen bonding in the organization and dynamics of gramicidin channels. Chaudhuri A, Haldar S, Sun H, et al. Biochim. Biophys. Acta 1838(1 Pt B), 419-28, (2014)

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MauG, a diheme enzyme that catalyzes tryptophan tryptophylquinone biosynthesis by remote catalysis. Shin S and Davidson VL Arch. Biochem. Biophys. 544, 112-8, (2014)

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Merck 14,9797

Beil. 22,V,14,14

Corp MSDS 1 (2), 3554:C / FT-IR 2 (3), 3595:D / FT-IR 1 (2), 671:D / FT-NMR 1 (3), 144:B / IR-Spectra (3), 1256:A / IR-Spectra (2), 1092:A / RegBook 1 (2), 2415:A / Sax 6, 2702 / Sigma FT-IR 1 (1), 275:A / Structure Index 1, 383:E:2

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