| Size | Price | |
|---|---|---|
| 5g | ||
| Other Sizes |
| Targets |
When incorporated into peptides, (R)-2-Amino-3-(3-nitrophenyl)propanoic acid can target a variety of receptors and enzymes depending on the peptide context. D-amino acids in peptides confer resistance to proteases, potentially increasing half-life. The nitro group can act as an electron-withdrawing group, modulating pi-pi interactions with aromatic residues in binding pockets. Specific targets include neuropeptide receptors (opioid, cholecystokinin), integrins, and enzymes (proteases, kinases). The free amino acid itself has no defined target. It is classified as a Phenylalanine derivative.
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| ln Vitro |
Commercial ergot supplements have been made from amino acids and their derivatives. They affect the release of anabolic hormones, the availability of fuel for activity, the ability to think clearly under pressure, and the prevention of muscular damage brought on by exertion. They are regarded as advantageous synergistic food ingredients [1].
The free amino acid has no reported in vitro biological activity. When incorporated into peptides, D-3-nitrophenylalanine residues can enhance the potency and stability of therapeutic peptides. For example, D-Phe-containing opioid peptides show increased micro-opioid receptor binding and resistance to degradation. No IC50 or EC50 data for the free amino acid are available. |
| ln Vivo |
No in vivo activity data are available for the free amino acid. Peptides containing D-3-nitrophenylalanine may be evaluated in animal models of pain, cancer, or metabolic disease. For instance, D-Phe-containing peptides administered intraperitoneally (10-30 mg/kg) in mice show prolonged analgesia in tail-flick tests compared to L-Phe analogs. No data exist for the building block alone.
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| Enzyme Assay |
The compound is not used directly in enzyme binding assays. For chemical characterization, standard HPLC with a C18 column and UV detection (210 nm and 260 nm for nitro group) is used. NMR in DMSO-d₆ or D2O confirms structure. For chiral purity, chiral HPLC with a Chiralpak column (e.g., AD-H) is used. Solubility: soluble in DMSO, slightly soluble in water. No biological binding protocols.
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| Cell Assay |
No cell-based protocols are established for this free amino acid. For peptide synthesis containing this residue: In SPPS, Fmoc-D-3-nitrophenylalanine (commercially available) is coupled using HATU/DIEA in DMF. After peptide assembly, the peptide is cleaved from resin with TFA/TIS/H2O. The final peptide is purified by HPLC and characterized by MS. The free amino acid is not used in cell assays.
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| Animal Protocol |
No animal studies have been conducted with the free amino acid. For D-3-nitrophenylalanine-containing peptides, typical in vivo studies: mice (C57BL/6, 8 weeks) are injected intraperitoneally with peptide (1-20 mg/kg). Blood is collected at 0, 1, 2, 4, 8, 24 hours. Plasma peptide concentration is measured by LC-MS/MS to calculate half-life and AUC. Efficacy in disease models (e.g., xenograft) can also be evaluated. No data for the building block.
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| ADME/Pharmacokinetics |
No PK data are available for (R)-2-Amino-3-(3-nitrophenyl)propanoic acid. It is not a drug candidate. As a D-amino acid, it may be slowly metabolized by D-amino acid oxidase (DAO) in the kidney and liver, producing 3-nitrophenylpyruvic acid and ammonia. Oral bioavailability is likely low due to intestinal transport preference for L-amino acids. Solubility: low in water; soluble in DMSO. No ADME studies reported.
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| Toxicity/Toxicokinetics |
Safety: The nitro group may contribute to potential mutagenicity (nitroaromatics can be genotoxic after metabolic reduction). Handle with caution. May cause skin and eye irritation. Harmful if swallowed. Not classified as carcinogen. Use standard PPE: gloves, lab coat, safety goggles, fume hood. Avoid inhalation of dust. Store at -20degC, desiccated, protected from light.
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| References |
[1]. Luckose F, et al. Effects of amino acid derivatives on physical, mental, and physiological activities. Crit Rev Food Sci Nutr. 2015;55(13):1793-980.
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| Additional Infomation |
(R)-2-Amino-3-(3-nitrophenyl)propanoic acid is not an approved drug and has no clinical trial history. It is a research chemical for peptide synthesis and medicinal chemistry. D-Phenylalanine derivatives are used to create protease-resistant, metabolically stable therapeutic peptides. The 3-nitro-D-phenylalanine residue can also be reduced to 3-amino-D-phenylalanine (via hydrogenation with Pd/C or SnCl2/HCl), providing a reactive primary amine for further conjugation (e.g., to fluorescent dyes, PEG, or targeting ligands). This makes it a versatile intermediate for peptide-drug conjugates (PDCs) and chemical biology probes. Commercially available for research use only.
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| Molecular Formula |
C9H10N2O4
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|---|---|
| Molecular Weight |
210.19
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| Exact Mass |
210.064
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| CAS # |
169530-97-6
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| PubChem CID |
7000156
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| Appearance |
Light brown to brown solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
410.8±35.0 °C at 760 mmHg
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| Flash Point |
202.3±25.9 °C
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| Vapour Pressure |
0.0±1.0 mmHg at 25°C
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| Index of Refraction |
1.614
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| LogP |
0.84
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
15
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| Complexity |
251
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| Defined Atom Stereocenter Count |
1
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| SMILES |
O([H])C([C@@]([H])(C([H])([H])C1C([H])=C([H])C([H])=C(C=1[H])[N+](=O)[O-])N([H])[H])=O
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| InChi Key |
YTHDRUZHNYKZGF-MRVPVSSYSA-N
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| InChi Code |
InChI=1S/C9H10N2O4/c10-8(9(12)13)5-6-2-1-3-7(4-6)11(14)15/h1-4,8H,5,10H2,(H,12,13)/t8-/m1/s1
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| Chemical Name |
(2R)-2-amino-3-(3-nitrophenyl)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 |
| 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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.7576 mL | 23.7880 mL | 47.5760 mL | |
| 5 mM | 0.9515 mL | 4.7576 mL | 9.5152 mL | |
| 10 mM | 0.4758 mL | 2.3788 mL | 4.7576 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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