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| Other Sizes |
| ln Vitro |
DL-m-Tyrosine exhibited phytotoxic activity in plant root growth assays. For lettuce (Lactuca sativa) radicle elongation, the IC50 values for D- and L-enantiomers were 17 µM and 21 µM, respectively, in a filter paper bioassay. [2]
In an agar-based Arabidopsis thaliana root growth assay, L-m-tyrosine was 10 times more toxic (IC50 = 0.6 µM) than the D enantiomer (IC50 = 9.3 µM). [2] DL-m-Tyrosine inhibited root elongation of various monocot and dicot plant species with IC50 values ranging from 10 µM to 260 µM. Producing fescue species (Festuca rubra) were unaffected at concentrations up to 160 µM, while non-producing fescue species (Festuca longifolia, Festuca ovina) were strongly sensitive. [2] m-Tyrosine did not affect photosynthetic efficiency or chlorophyll production in lettuce seedlings. It did not inhibit the growth of bacteria (Escherichia coli, Bacillus cereus, Bacillus subtilis) or the soil fungus Metarhizium anisopliae at concentrations up to 25 mM. [2] In Arabidopsis, the toxicity of 3 µM DL-m-tyrosine was counteracted by addition of 40 µM each of 14 protein amino acids, with phenylalanine showing the most significant rescue effect. Charged amino acids caused little or no improvement. [2] m-Tyrosine treatment (10 µM for 2 days) led to its incorporation into Arabidopsis root proteins, representing less than 1% of total phenylalanine in the protein fraction (0.88 ± 0.006% of phenylalanine). [2] Wild-type phenylalanine ammonia-lyase (PAL) from parsley converted DL-m-tyrosine at a rate comparable to L-phenylalanine, with kinetic parameters: Vmax = 0.50 units/mg, Km = 0.20 mM. [1] |
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| ln Vivo |
In filter paper bioassays, lettuce (Lactuca sativa) seedlings were exposed to various concentrations of DL-m-Tyrosine (10-320 µM) for 5 days, and radicle and shoot lengths were measured. Dose-response curves were fitted to a four-parameter logistic function to determine IC50 values. [2]
In agar plate bioassays with Arabidopsis thaliana, seeds were germinated on half-strength Murashige and Skoog medium containing 1% sucrose and 1% Phytagar, supplemented with DL-m-Tyrosine (0-320 µM). After cold stratification for 24 h at 4°C, plates were placed vertically in growth chambers (23°C, 180 µmol m⁻² s⁻¹, 16:8 h light/dark). Root lengths of 10 seedlings per plate were measured after 5 days. [2] For rescue experiments, 40 µM of individual protein amino acids were added to agar plates containing 3 µM DL-m-Tyrosine, and root growth of Arabidopsis was assessed after 1 week. [2] m-Tyrosine-producing fescue (Festuca rubra cv. Intrigue) and non-producing fescue species were tested for sensitivity using the same filter paper assay with 0-160 µM DL-m-tyrosine. [2] |
| Enzyme Assay |
The enzyme assay for phenylalanine ammonia-lyase (PAL) activity was performed spectrophotometrically. For L-phenylalanine, L-tyrosine, and DL-m-tyrosine as substrates, the conversion was monitored at 290 nm. For L-4-nitrophenylalanine, the conversion was monitored at 340 nm. The assay buffer was 50 mM potassium phosphate (pH 7.0) containing 5 mM phenylalanine (for stabilization). Substrate concentrations were varied between 0.05 mM and 7 mM, and Km and Vmax values were determined using double reciprocal plots. [1]
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| Cell Assay |
No cell-based assays (as defined for mammalian or microbial cell lines) were performed in the provided literature. However, plant seedling root growth assays (described under In Vivo) and amino acid incorporation studies in Arabidopsis roots are reported. For measurement of protein-incorporated m-tyrosine, Arabidopsis seedlings were transferred to agar plates with 10 µM m-tyrosine for 2 days. Roots were harvested, frozen, and ground. Protein was extracted in PBS buffer with PMSF, and free amino acids were removed by centrifugation through spin columns. Protein samples were hydrolyzed in 6 M HCl with 1% phenol at 110°C for 24 h under argon, then dried and analyzed by HPLC-fluorescence after derivatization with AccQ tag. [2]
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| Toxicity/Toxicokinetics |
DL-m-Tyrosine showed phytotoxicity to plant root growth with IC50 values ranging from 10 µM to 260 µM across various plant species. It did not inhibit the growth of bacteria (Escherichia coli, Bacillus cereus, Bacillus subtilis) or a soil fungus (Metarhizium anisopliae) at concentrations as high as 25 mM. [2]
No mammalian toxicity data (e.g., LD50, hepatotoxicity, protein binding) are reported in the provided literature. [1][2] |
| References | |
| Additional Infomation |
DL-m-tyrosine is a derivative of phenylalanine.
DL-m-Tyrosine is a non-protein amino acid exuded by roots of fine fescue grasses (e.g., Festuca rubra) as an allelochemical, displacing neighboring plants. It constitutes 33-43% of the dry weight of aqueous root exudate extract in cv. Intrigue. Its biosynthesis is initiated after germination, with concentrations in roots (6,500 pmol/mg wet weight) being 10-fold higher than in leaves (590 pmol/mg). [2] Proposed mechanism of action: misincorporation into plant proteins in place of phenylalanine, causing structural disruptions or interference with tyrosine-specific functions. It is accepted by Vigna radiata phenylalanine-tRNA synthase with 25% of the efficiency of phenylalanine. [2] In phenylalanine ammonia-lyase (PAL) from parsley, m-tyrosine is a substrate. The enzyme's mechanism involves electrophilic attack of the dehydroalanine prosthetic group on the aromatic ring, and the m-hydroxy group facilitates this attack at the ortho position relative to the side chain. [1] Compared to its isomers, p-tyrosine and o-tyrosine stimulated lettuce root growth at low concentrations (50 µM), whereas m-tyrosine was inhibitory. m-Hydroxyphenylpyruvate (the deaminated form) had an IC50 for Arabidopsis root elongation 5-fold higher than that of m-tyrosine. [2] |
| Molecular Formula |
C9H11NO3
|
|---|---|
| Molecular Weight |
181.18854
|
| Exact Mass |
181.073
|
| CAS # |
775-06-4
|
| Related CAS # |
DL-m-Tyrosine-d3
|
| PubChem CID |
13052
|
| Appearance |
Off-white to light yellow powder
|
| Density |
1.3±0.1 g/cm3
|
| Boiling Point |
387.2±32.0 °C at 760 mmHg
|
| Melting Point |
280-285 °C (dec.)(lit.)
|
| Flash Point |
188.0±25.1 °C
|
| Vapour Pressure |
0.0±0.9 mmHg at 25°C
|
| Index of Refraction |
1.614
|
| LogP |
0.38
|
| Hydrogen Bond Donor Count |
3
|
| Hydrogen Bond Acceptor Count |
4
|
| Rotatable Bond Count |
3
|
| Heavy Atom Count |
13
|
| Complexity |
184
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
OC(C(CC1C=CC=C(C=1)O)N)=O
|
| InChi Key |
JZKXXXDKRQWDET-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C9H11NO3/c10-8(9(12)13)5-6-2-1-3-7(11)4-6/h1-4,8,11H,5,10H2,(H,12,13)
|
| Chemical Name |
2-amino-3-(3-hydroxyphenyl)propanoic acid
|
| Synonyms |
DL-m-Tyrosine
|
| HS Tariff Code |
2934.99.9001
|
| 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)
|
| Solubility (In Vitro) |
H2O : ~1.43 mg/mL (~7.89 mM)
Water : ~6 mg/mL |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: 5 mg/mL (27.60 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.
(Please use freshly prepared in vivo formulations for optimal results.) |
| 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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