D tryptophan

Manufactured by Merck Group

Sourced in United States, Germany

D-tryptophan is a naturally occurring amino acid that serves as a key component in various laboratory applications. It is a white crystalline powder that is soluble in water and other polar solvents. D-tryptophan is often used as a chemical standard and a building block for the synthesis of other compounds in research and development settings.

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Close spelling variants of this product

1-methyl-D-tryptophan 1-methyl-D-tryptophan (MT, 1-Methyl-d-tryptophan (1-MT, 1-Methyl-D-tryptophan (1-D-MT) Tryptophan

10 protocols using d tryptophan

Stereochemistry of Pharmaceutical Compounds

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All
molecules studied were purchased from
Merck-Sigma (Gillingham, U.K.) as follows: (R)-thalidomide
(T151), (S)-thalidomide (T150), d-penicillamine
(P4875), l-penicillamine (196312), l-tryptophan
(T8941), d-tryptophan (T9753), (R)-propanolol
(P0689), and (S)-propanolol (P8688).

Cooper-Shepherd D.A., Olivos H.J., Wu Z, & Palmer M.E. (2022). Exploiting Self-Association to Evaluate Enantiomeric Composition by Cyclic Ion Mobility–Mass Spectrometry. Analytical Chemistry, 94(23), 8441-8448.

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Quantitative Analysis of Kynurenine Pathway

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Kynurenic acid-d5 (2.5 mg), L-Kynurenine-d4 [2-aminophenyl-3,5-d2] (5 mg), 2,3-pyridinedicarboxylic acid-d3 (Major) (1 mg) were purchased from TRC Research Chemical. D-tryptophan (Indole-D5, 98%) (50 mg) was purchased from Cambridge Isotope Laboratories. D-Kynurenine free base (25 mg), 2,3-dicarboxylic acid, 99% (25 g), D-tryptophan, = 98.0% (HPLC) (1 g) was purchased from MERCK. UPLC water and acetonitrile, 99%, was purchased from Honeywell. Formic acid for LC-MS was purchased from Merck.

Asia L.K., Van Vuren E.J., Lindeque Z, & Williams M.E. (2024). A pilot investigation of the association between HIV-1 Vpr amino acid sequence diversity and the tryptophan-kynurenine pathway as a potential mechanism for neurocognitive impairment. Virology Journal, 21, 47.

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Tryptophan and Monoamine Biosynthesis Assay

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L-tryptophan, D-tryptophan, DL-tryptophan, tryptamine, 5-hydroxy-L-tryptophan, 5-fluoro-DL-tryptophan, 5-bromo-DL-tryptophan, L-tryptophan-benzyl ester, L-tryptophan -methyl ester, serotonin, dopamine hydrochloride, 3,4-dihydroxy-L-phenylalanine (L-DOPA), sodium ascorbate, Luria-Bertani medium (LB), carbenicillin, chloramphenicol, kanamycin sulfate, and isopropyl β-D-1-thiogalactopyranoside (IPTG) were purchased from Merck KGaA (Darmstadt, Germany). Ammonium hydroxide, TRIzol, acetonitrile, and HPLC-grade water were obtained from Fisher Scientific (Leicester, UK).

Henarejos-Escudero P., Méndez-García F.F., Hernández-García S., Martínez-Rodríguez P, & Gandía-Herrero F. (2023). Design, Synthesis and Gene Modulation Insights into Pigments Derived from Tryptophan-Betaxanthin, Which Act against Tumor Development in Caenorhabditis elegans. International Journal of Molecular Sciences, 25(1), 63.

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Amino Acid Synthesis and Characterization

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d-Alanine, d-Arginine, d-Asparticacid, d-Asparagine, d-Glutamicacid, d-Histidine, d-Isoleucine, d-Leucine, d-Lysine, d-Methionine, d-Phenylalanine, d-Proline, d-Serine, d-Threonine, d-Tryptophan, d-Tyrosine, d-Valine, KBr (spectral grade), bovine serum albumin (BSA), glutathione and 3,3′,5,5′-tetramethylbenzidine (TMB) were purchased from Sigma-Aldrich Chemical Co. (St. Louis, MO, USA). d-Cystine and d-Glutarnine were purchased from Aladdin Reagent Co, Ltd. (Shanghai, China). All other chemicals and reagents were of analytical grade. All aqueous solutions were prepared with Milli-Q water.

Jiang N., Zhang C., Li M., Li S., Hao Z., Li Z., Wu Z, & Li C. (2021). The Fabrication of Amino Acid Incorporated Nanoflowers with Intrinsic Peroxidase-like Activity and Its Application for Efficiently Determining Glutathione with TMB Radical Cation as Indicator. Micromachines, 12(9), 1099.

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Tryptophan Metabolism Quantification

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D-Tryptophan (D-TRP), L-tryptophan (L-TRP), D-kynurenine (D-KYN), kynurenic acid (KYNA), 3-hydroxy-DL-kynurenine (3-HK), quinolinic acid (QUIN), D-amino acid oxidase (D-AAO, purified from porcine kidney; product number A5222) and 3-methylpyrazole-5-carboxylic acid (MPC) were purchased from Sigma-Aldrich (St. Louis, MO, USA). L-Kynurenine (L-KYN) was obtained from Sai Advantium (Hyderabad, India), and [²H₃]-QUIN was purchased from Synfine Research (Richmond Hill, Ontario, Canada).
All other chemicals were purchased from various commercial suppliers and were of the highest available purity.

Notarangelo F.M., Wang X.D., Horning K.J, & Schwarcz R. (2016). Role of D-amino acid oxidase in the production of kynurenine pathway metabolites from D-tryptophan in mice. Journal of neurochemistry, 136(4), 804-814.

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Comparative Sweetener Compound Analysis

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HEK293E cell was purchased from Invitrogen. Aspartame, saccharin, cyclamate, sucrose, D-tryptophan, NHDC, perillartine, amiloride, monellin and thaumatin were obtained from Sigma-Aldrich. Neotame was obtained from American Health Foods & Ingredients. Stevioside was purchased from Nusci Institute & Corp. Unless stated, all other chemicals and reagents were from Sangon Biotech (Shanghai, China).

Cai C., Jiang H., Li L., Liu T., Song X, & Liu B. (2016). Characterization of the Sweet Taste Receptor Tas1r2 from an Old World Monkey Species Rhesus Monkey and Species-Dependent Activation of the Monomeric Receptor by an Intense Sweetener Perillartine. PLoS ONE, 11(8), e0160079.

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Metabolite Identification by LC-MS

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LC–MS grade methanol, water and formic acid as well as the standard mixtures used for the external calibration of the MS instrument were from Thermo Fisher Scientific (MA, USA). All analytical grade reference compound (glycocholic acid, d-tryptophan, N-acetyl-l-tryptophan, L-kynurenine and Kynurenic acid) were from Sigma Aldrich (Steinheim, Germany).

Simonato M., Fochi I., Vedovelli L., Giambelluca S., Carollo C., Padalino M., Carnielli V.P, & Cogo P. (2019). Urinary metabolomics reveals kynurenine pathway perturbation in newborns with transposition of great arteries after surgical repair. Metabolomics, 15(11), 145.

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Preparation of Amino Acid Solutions

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D-methionine, D-tryptophan, D-leucine, D- or L-cysteine, D- or L-aspartic acid, D- or L-glutamic acid, D-alanine, D-threonine, D-valine, D-isoleucine, D-glutamine, D-phenylalanine, D-histidine, D-proline, D-lysine, D-arginine, and glycine (Sigma-Aldrich, St. Louis, MO, USA) were all prepared at a concentration of 40 mM, and D-tyrosine was prepared at a concentration of 0.8 mM due to its low solubility. Nisin powder (2.5% purity, Sigma-Aldrich, St. Louis, MO, USA) was dissolved in a solution at pH 2 to obtain a stock solution with a concentration of 1 g/L.

Tong Z., Zhang L., Ling J., Jian Y., Huang L, & Deng D. (2014). An In Vitro Study on the Effect of Free Amino Acids Alone or in Combination with Nisin on Biofilms as well as on Planktonic Bacteria of Streptococcus mutans. PLoS ONE, 9(6), e99513.

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Sweetener Compounds Characterization

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D‐tryptophan (product number T9753, purity ≥98%) was purchased from Sigma‐Aldrich (St. Louis, MO, USA). Sucralose (product number 29329990.99, purity ≈99.2%) was obtained from Tongyuan Sweetener Co. Ltd (Huanggang, China). Stevioside (purity ≈90%) was obtained from NuSci Institute & Corp (Walnut, CA, USA). Saccharin (product number 47839, purity ≈99.9%) was obtained from Supelco (Bellefonte, PA, USA). All other chemicals and reagents were analytical grade and were from Invitrogen (La Jolla, CA, USA).

Zhao X., Liu M., Cui M, & Liu B. (2021). Multiple interaction modes between saccharin and sweet taste receptors determine a species‐dependent response to saccharin. FEBS Open Bio, 12(2), 494-499.

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Comprehensive Experimental Asthma Protocol

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For detailed information on reagents, culture conditions of bacteria and human cells, generation of human monocyte-derived dendritic cells (DCs), structural elucidation of D-tryptophan (Sigma-Aldrich, St Louis, Mo), cytokine/chemokine quantification, murine T-cell differentiation, flow cytometry, quantitative RT-PCR, microbiota analysis, isolation of intestinal lamina propria cells, and animal experiments (induction of experimental asthma and lung function analyses), see the Methods section in this article's Online Repository at www.jacionline.org.

Kepert I., Fonseca J., Müller C., Milger K., Hochwind K., Kostric M., Fedoseeva M., Ohnmacht C., Dehmel S., Nathan P., Bartel S., Eickelberg O., Schloter M., Hartmann A., Schmitt-Kopplin P, & Krauss-Etschmann S. (2017). D-tryptophan from probiotic bacteria influences the gut microbiome and allergic airway disease. The Journal of allergy and clinical immunology, 139(5).

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