| Size | Price | Stock | Qty |
|---|---|---|---|
| 25g |
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| Other Sizes |
| Targets |
H-D-Trp-OH exhibits bioactivity primarily as an activator of various carbonic anhydrase (CA) isoforms, including human recombinant CA1 (KA = 41.0 µM), CA2 (KA = 12.0 µM), CA3 (KA = 19.0 µM), and CA6 (KA = 39.0 µM). It also activates mouse recombinant CA13 (KA = 0.81 µM) and other non-human CA enzymes with KA values as low as 0.002 µM. Additionally, it shows weak inhibitory effects on stromelysin (IC50 > 500,000 nM), human dihydrofolate reductase (Ki = 880,000 nM), LAT1 (IC50 = 380,000 nM), and HDAC6.
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| ln Vitro |
H-D-Trp-OH activates carbonic anhydrase enzymes in cell-free biochemical assays with KA values ranging from 0.002 µM to 41.0 µM depending on the isoform and species. It exhibits weak inhibition of stromelysin catalytic domain (IC50 > 500,000 nM), human dihydrofolate reductase (Ki = 880,000 nM), and LAT1 (IC50 = 380,000 nM).
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| ln Vivo |
H-D-Trp-OH has been shown to increase intestinal microbial diversity in mouse models and counteract the inhibitory effects of allergic airway inflammation on gut microbial diversity. Oral administration in drinking water at ~0.09 or ~0.9 mg/day/mouse for 3 days prevented experimental asthma, increased regulatory T cells in the lung and intestine, reduced lung TH2 responses, and improved allergic airway inflammation and hyperresponsiveness.
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| Enzyme Assay |
For carbonic anhydrase activation assays, recombinant human CA isoforms are incubated with varying concentrations of H-D-Trp-OH and the substrate 4-nitrophenyl acetate; activation constants (KA) are determined from Lineweaver-Burk plots. For enzyme inhibition studies, assays are performed using appropriate substrates (e.g., stromelysin, dihydrofolate reductase) with IC50 or Ki values calculated from dose-response curves.
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| Cell Assay |
Cellular assays typically evaluate H-D-Trp-OH effects on immune cell populations. In murine models, flow cytometry is used to quantify regulatory T cell populations in lung and intestinal tissues following oral administration. Cytokine profiling (TH2 responses) is measured via ELISA or multiplex assays from tissue homogenates or bronchoalveolar lavage fluid.
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| Animal Protocol |
In mouse models of allergic airway inflammation, H-D-Trp-OH is administered orally via drinking water at ~0.09 or ~0.9 mg/day/mouse for 3 days. Asthma is induced by standard allergen sensitization and challenge protocols. Endpoints include airway hyperresponsiveness measured by methacholine challenge, inflammatory cell infiltration in bronchoalveolar lavage, TH2 cytokine levels, and regulatory T cell enumeration in lung and intestinal tissues via flow cytometry.
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| ADME/Pharmacokinetics |
As an endogenous amino acid, D-tryptophan is absorbed through dietary intake and amino acid transporters. It is metabolized through the kynurenine pathway and other tryptophan metabolic routes. Oral bioavailability is expected to be moderate with systemic distribution to tissues including the lungs and intestines, where it exerts immunomodulatory effects.
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| Toxicity/Toxicokinetics |
D-Tryptophan is generally recognized as safe as a dietary amino acid. The D-isomer is less commonly utilized in protein synthesis compared to L-tryptophan but is well-tolerated at physiological doses. In murine studies, oral administration at ~0.09–0.9 mg/day/mouse showed no overt toxicity.
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| Additional Infomation |
D(+)-Tryptophan is a white solid. (NTP, 1992)
D-Tryptophan is the D-enantiomer of tryptophan. It is a bacterial metabolite. It is a tryptophan and also a D-α-amino acid. It is the conjugate base of D-tryptophanonium. It is the conjugate acid of D-tryptophan acid. It is an enantiomer of L-tryptophan. It is a tautomer of D-tryptophan zwitterion. Tryptophan is one of the 20 standard amino acids and an essential amino acid in the human diet. It is encoded by the UGG codon in the standard genetic code. D-stereoisomers are occasionally found in naturally occurring peptides (e.g., marine venom peptide tryptophan). A prominent structural feature of tryptophan is that it contains an indole functional group. Based on its effect on rat growth, D-Tryptophan is an essential amino acid. D-Tryptophan has been reported in tomatoes (Solanum lycopersicum) and grapes (Vitis vinifera), and relevant data are available. See also: tryptophan (note moved here). H-D-Trp-OH is a non-proteinogenic amino acid found in marine venom peptides such as contryphan. It functions as a carbonic anhydrase activator and has shown promise in modulating gut microbiome composition and allergic airway inflammation through regulatory T cell expansion. It is a research tool for studying amino acid stereochemistry, carbonic anhydrase biology, and gut-lung axis immunomodulation. |
| Molecular Formula |
C11H12N2O2
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|---|---|
| Molecular Weight |
204.2252
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| Exact Mass |
204.089
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| CAS # |
153-94-6
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| Related CAS # |
L-Tryptophan;73-22-3;H-D-Trp-OH-d5;1202359-57-6
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| PubChem CID |
9060
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| Appearance |
White to off-white solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
447.9±35.0 °C at 760 mmHg
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| Melting Point |
282-285ºC
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| Flash Point |
224.7±25.9 °C
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| Vapour Pressure |
0.0±1.1 mmHg at 25°C
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| Index of Refraction |
1.698
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| LogP |
1.04
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
15
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| Complexity |
245
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| Defined Atom Stereocenter Count |
1
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| SMILES |
O([H])C([C@@]([H])(C([H])([H])C1=C([H])N([H])C2=C([H])C([H])=C([H])C([H])=C12)N([H])[H])=O
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| InChi Key |
QIVBCDIJIAJPQS-SECBINFHSA-N
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| InChi Code |
InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m1/s1
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| Chemical Name |
(2R)-2-amino-3-(1H-indol-3-yl)propanoic acid
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: (1). This product requires protection from light (avoid light exposure) during transportation and storage. (2). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~3.33 mg/mL (~16.31 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 0.33 mg/mL (1.62 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 3.3 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 0.33 mg/mL (1.62 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 3.3 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 0.33 mg/mL (1.62 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.8964 mL | 24.4822 mL | 48.9644 mL | |
| 5 mM | 0.9793 mL | 4.8964 mL | 9.7929 mL | |
| 10 mM | 0.4896 mL | 2.4482 mL | 4.8964 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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