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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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Other Notes

Amino acid precursor of serotonin and melatonin

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1 kg in poly bottle

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

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<SC>L</SC>-Tryptophan

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)

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Safety Information

WGK Germany 
1
RTECS 
YN6130000

Documents

Certificate of Analysis

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Protocols & Articles

Related Content

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Peer-Reviewed Papers

References

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

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

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

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

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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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