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| Targets |
The primary target of L-2-Aminooxy-3-phenylpropanoic acid is L-phenylalanine ammonia-lyase (PAL), which it inhibits as a blocker/antagonist. By binding to the active site of PAL, AOPP prevents the conversion of L-phenylalanine to trans-cinnamic acid, thereby blocking the entry point of the phenylpropanoid pathway. This inhibition has downstream effects on the production of lignin, flavonoids, and other phenylpropanoid-derived compounds in plants.
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| ln Vitro |
In vitro studies demonstrate that L-2-Aminooxy-3-phenylpropanoic acid (10 μM) reduces the proportion of lignified tracheary elements and the lignin content in lignified tracheary elements in Zinnia elegans leaf mesophyll cells. It also causes an increase in ionically tightly bound peroxidase activity. The compound inhibits lignification without reducing the number of tracheary elements formed, indicating a specific effect on the lignification process rather than on cell differentiation.
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| ln Vivo |
In vivo studies have confirmed that L-2-Aminooxy-3-phenylpropanoic acid acts as a potent inhibitor of L-phenylalanine ammonia-lyase in living plant systems. The compound effectively inhibits lignification in plant tissues, as demonstrated in various plant models. Its in vivo activity makes it a valuable tool for studying the physiological roles of PAL and the phenylpropanoid pathway in whole plants, particularly in relation to lignin biosynthesis and plant defense responses.
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| Enzyme Assay |
Non-cellular enzyme inhibition assays for L-2-Aminooxy-3-phenylpropanoic acid typically involve incubating the compound with purified L-phenylalanine ammonia-lyase (PAL) enzyme and its substrate L-phenylalanine. The reaction is monitored spectrophotometrically by measuring the formation of trans-cinnamic acid at 290 nm. IC50 values are determined by testing a range of inhibitor concentrations. These cell-free systems allow for direct assessment of the compound's inhibitory potency without interference from cellular uptake or metabolism.
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| Cell Assay |
Cellular assays for L-2-Aminooxy-3-phenylpropanoic acid are conducted using plant cell culture systems such as Zinnia elegans leaf mesophyll cells. Cells are treated with the compound at concentrations around 10 μM, and the proportion of lignified tracheary elements is quantified microscopically. Lignin content is measured using phloroglucinol-HCl staining or UV absorbance. Peroxidase activity is assayed spectrophotometrically using guaiacol or other substrates.
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| Animal Protocol |
In vivo animal experiments for L-2-Aminooxy-3-phenylpropanoic acid are not typically conducted, as the compound is primarily used in plant research. However, it has been studied in plant models where it is administered through the growth medium or by infiltration into plant tissues. The compound inhibits lignification in whole plants, and effects are assessed by measuring lignin content, tracheary element formation, and phenylpropanoid pathway metabolite levels.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of L-2-Aminooxy-3-phenylpropanoic acid are not well-characterized, as the compound is primarily used in plant research rather than as a therapeutic agent. It is soluble in DMSO (250 mg/mL) and has moderate solubility in aqueous formulations. The compound is stable as a powder at -20°C for up to 3 years. For in vivo plant studies, it is typically applied through the growth medium or by infiltration into plant tissues.
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| Toxicity/Toxicokinetics |
Toxicological data for L-2-Aminooxy-3-phenylpropanoic acid are limited, as the compound is not intended for human therapeutic use. It is considered a research chemical with potential toxicity if ingested or absorbed through the skin. Standard laboratory safety precautions should be followed when handling this compound. It is not approved for human use and should be handled only by trained personnel in appropriate facilities.
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| References |
[1]. NikolausAmrhein, et al. α-aminooxy-β-phenylpropionic acid — a potent inhibitor of L-phenylalanine ammonia-lyase in vitro and in vivo. Plant Science Letters Volume 8, Issue 4, April 1977, Pages 313-317.
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| Additional Infomation |
alpha-Aminooxy-beta-phenylpropionic acid is the (S)-isomer.
L-2-Aminooxy-3-phenylpropanoic acid is primarily used as a research tool in plant biochemistry to study the phenylpropanoid pathway and lignification. It has no clinical or therapeutic applications and has not been evaluated in human trials. The compound is valuable for investigating the role of PAL in plant growth, development, and stress responses. It may also be used in studies of secondary metabolite production and plant defense mechanisms. |
| Molecular Formula |
C9H11NO3
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|---|---|
| Molecular Weight |
181.19
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| Exact Mass |
181.074
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| CAS # |
42990-62-5
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| PubChem CID |
170717
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| Appearance |
White to off-white solid powder
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| LogP |
1.272
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
13
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| Complexity |
172
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1(C=CC=CC=1)C[C@H](ON)C(=O)O
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| InChi Key |
CGVPQHIRIGIDLE-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C9H11NO3/c10-13-8-4-2-1-3-7(8)5-6-9(11)12/h1-4H,5-6,10H2,(H,11,12)
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| Chemical Name |
3-(2-aminooxyphenyl)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) |
DMSO: 250 mg/mL (1379.77 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (11.48 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 20.8 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: ≥ 2.08 mg/mL (11.48 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 20.8 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: ≥ 2.08 mg/mL (11.48 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 | 5.5191 mL | 27.5953 mL | 55.1907 mL | |
| 5 mM | 1.1038 mL | 5.5191 mL | 11.0381 mL | |
| 10 mM | 0.5519 mL | 2.7595 mL | 5.5191 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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