| Size | Price | Stock | Qty |
|---|---|---|---|
| 100mg |
|
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| 500mg |
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| Targets |
- O-Acetylserine regulates the expression of genes encoding components for sulfate uptake (e.g., SULTR1;1, SULTR1;2) and assimilation (e.g., APS1, APR1, SAT1) in plants[1]
- O-Acetylserine induces the expression of sulfate transporter genes (StSULTR1;1, StSULTR1;2) and adenosine 5'-phosphosulfate (APS) reductase gene (StAPR1) in potato [2] |
|---|---|
| ln Vitro |
O-Acetylserine (OAS) serves as the carbon skeleton for cysteine production and is a key metabolite of sulfur absorption. Cysteine is formed when OAS absorbs sulfide, which is produced when sulfate reacts. Regardless of the sulfate status of the plant, OAS has a signaling role that causes modifications in the transcript levels of particular genomes [1]. The transcriptional induction model of OAS is in line with the increased expression of the sulfate transporter and adenosine 5'-phosphate reductase genes after external OAS treatment [2].
- In Arabidopsis root protoplasts, treatment with O-Acetylserine (1 mM) upregulated the expression of SULTR1;1, SULTR1;2, APS1, and APR1 genes (detected by quantitative real-time PCR, qPCR), regardless of the external sulfate concentration. This indicated O-Acetylserine acts as a sulfur status-independent regulator of these genes [1] - In suspension-cultured potato cells, exogenous application of O-Acetylserine (0.5 mM, 1 mM) increased the transcript levels of StSULTR1;1, StSULTR1;2, and StAPR1 (analyzed by Northern blot and qPCR) within 2–4 hours. The induction was more pronounced under sulfur-deficient conditions but still observable under sulfur-sufficient conditions [2] - In vitro enzyme activity assay showed that O-Acetylserine did not directly inhibit or activate adenosine 5'-phosphosulfate reductase (APR) or serine acetyltransferase (SAT) activity in Arabidopsis; its regulatory role is mainly at the transcriptional level [1] |
| ln Vivo |
- In Arabidopsis seedlings grown under sulfur-sufficient (1.5 mM SO4^2-) or sulfur-deficient (0.015 mM SO4^2-) conditions, exogenous O-Acetylserine (1 mM, applied via hydroponic solution) increased the root-specific expression of SULTR1;1 and SULTR1;2 (monitored by GUS reporter assay) and enhanced sulfate uptake rate (measured by ^35S-sulfate uptake assay) by 2–3 folds in both sulfur conditions [1]
- In potato plants grown in sulfur-deficient soil, foliar spray of O-Acetylserine (10 mM) restored the expression of StSULTR1;1, StSULTR1;2, and StAPR1 to levels similar to sulfur-sufficient plants, and increased the total sulfur content in leaves by ~40% compared to untreated sulfur-deficient plants [2] |
| Enzyme Assay |
- For adenosine 5'-phosphosulfate reductase (APR) activity assay: Arabidopsis leaf extracts were prepared in extraction buffer. The reaction mixture contained leaf extract, APS, glutathione (GSH), and different concentrations of O-Acetylserine (0–2 mM). The reaction was initiated by adding APS, incubated at 25°C for 30 minutes, and the amount of sulfite produced was measured by a colorimetric method. No significant change in APR activity was observed with O-Acetylserine treatment [1]
- For serine acetyltransferase (SAT) activity assay: Potato tuber extracts were mixed with acetyl-CoA, serine, and O-Acetylserine (0–1.5 mM) in reaction buffer. The reaction was carried out at 30°C for 20 minutes, and the remaining acetyl-CoA was quantified by reacting with 5,5'-dithio-bis-(2-nitrobenzoic acid) (DTNB). O-Acetylserine did not affect SAT activity in the tested concentration range [2] |
| Cell Assay |
- Arabidopsis root protoplast isolation and transfection: Roots of 7-day-old Arabidopsis seedlings were digested with cellulase and pectinase to obtain protoplasts. Protoplasts were transfected with reporter plasmids containing the promoter of SULTR1;1/SULTR1;2 fused to luciferase. After transfection, protoplasts were treated with O-Acetylserine (0.1–2 mM) for 6 hours, and luciferase activity was measured using a luminometer. The results showed O-Acetylserine dose-dependently enhanced promoter activity [1]
- Potato suspension cell culture and treatment: Potato suspension cells were maintained in liquid medium. At the exponential growth phase, cells were treated with O-Acetylserine (0.2–1.5 mM) under sulfur-sufficient (1 mM SO4^2-) or sulfur-deficient (0.01 mM SO4^2-) conditions. After 2, 4, 8, and 12 hours of treatment, cells were harvested, total RNA was extracted, and gene expression levels were analyzed by qPCR [2] |
| References | |
| Additional Infomation |
O-acetyl-L-serine is an acetyl-L-serine in which the acetyl group is attached to the oxygen atom of the side chain. It is an intermediate in the biosynthesis of the amino acid cysteine in bacteria. It is a metabolic product of both bacteria and Saccharomyces cerevisiae. It is an acetate and also an acetyl-L-serine. It is a zwitterion of O-acetyl-L-serine. O-acetylserine is a metabolite present in or produced by Escherichia coli (K12 strain, MG1655 strain). O-acetyl-L-serine has been reported to be present in Daphnia davidii, Arabidopsis thaliana and other organisms with relevant data. O-acetylserine is synthesized by serine acetyltransferase (SAT) in plant chloroplasts and mitochondria using serine and acetyl-CoA as substrates. O-acetylserine is both a substrate of cysteine synthase (OASTL), which participates in the synthesis of cysteine, and a signaling molecule that regulates sulfur uptake and assimilation[1]. In Arabidopsis, the regulatory effect of O-acetylserine on sulfur-related genes is independent of the transcription factor sulfur restriction 1 (SLIM1), which mediates the sulfur deficiency response. This suggests that O-acetylserine functions through an independent signaling pathway [1]. In potato, O-acetylserine levels in leaves and roots increase within 12 hours of sulfur deficiency, which is associated with the induction of sulfate transporters and assimilation genes. Exogenous O-acetylserine can replace sulfur deficiency to trigger the expression of these genes [2].
|
| Molecular Formula |
C5H9NO4
|
|---|---|
| Molecular Weight |
147.12926
|
| Exact Mass |
147.053
|
| CAS # |
5147-00-2
|
| PubChem CID |
99478
|
| Appearance |
White to off-white solid powder
|
| Density |
1.299g/cm3
|
| Boiling Point |
297.7ºC at 760mmHg
|
| Flash Point |
133.8ºC
|
| LogP |
-3.5
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
5
|
| Rotatable Bond Count |
4
|
| Heavy Atom Count |
10
|
| Complexity |
145
|
| Defined Atom Stereocenter Count |
1
|
| SMILES |
CC(=O)OC[C@@H](C(=O)O)N
|
| InChi Key |
VZXPDPZARILFQX-BYPYZUCNSA-N
|
| InChi Code |
InChI=1S/C5H9NO4/c1-3(7)10-2-4(6)5(8)9/h4H,2,6H2,1H3,(H,8,9)/t4-/m0/s1
|
| Chemical Name |
(2S)-3-acetyloxy-2-aminopropanoic acid
|
| 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 : ~50 mg/mL (~339.84 mM)
DMSO : ~6.25 mg/mL (~42.48 mM) |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 0.62 mg/mL (4.21 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 6.2 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: ≥ 0.62 mg/mL (4.21 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 6.2 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: ≥ 0.62 mg/mL (4.21 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: 100 mg/mL (679.67 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 6.7967 mL | 33.9836 mL | 67.9671 mL | |
| 5 mM | 1.3593 mL | 6.7967 mL | 13.5934 mL | |
| 10 mM | 0.6797 mL | 3.3984 mL | 6.7967 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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