sodium 4-pentynoatechemical reporter for the profiling of acetylated proteins CAS# 101917-30-0 |
- Tiratricol
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| Cas No. | 101917-30-0 | SDF | Download SDF |
| PubChem ID | 66577022 | Appearance | Powder |
| Formula | C5H5NaO2 | M.Wt | 120.08 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | H2O : 100 mg/mL (832.78 mM; Need ultrasonic) DMSO : 16.67 mg/mL (138.82 mM; Need ultrasonic) | ||
| Chemical Name | sodium;pent-4-ynoate | ||
| SMILES | C#CCCC(=O)[O-].[Na+] | ||
| Standard InChIKey | IWIICCMJXWKGSG-UHFFFAOYSA-M | ||
| Standard InChI | InChI=1S/C5H6O2.Na/c1-2-3-4-5(6)7;/h1H,3-4H2,(H,6,7);/q;+1/p-1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | sodium 4-pentynoate is a alkynylacetate analogue; can be metabolically incorporated onto cellular proteins through biosynthetic mechanisms for profiling of acetylated proteins in diverse cell types. References: | |||||
sodium 4-pentynoate Dilution Calculator
sodium 4-pentynoate Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 8.3278 mL | 41.6389 mL | 83.2778 mL | 166.5556 mL | 208.1945 mL |
| 5 mM | 1.6656 mL | 8.3278 mL | 16.6556 mL | 33.3111 mL | 41.6389 mL |
| 10 mM | 0.8328 mL | 4.1639 mL | 8.3278 mL | 16.6556 mL | 20.8195 mL |
| 50 mM | 0.1666 mL | 0.8328 mL | 1.6656 mL | 3.3311 mL | 4.1639 mL |
| 100 mM | 0.0833 mL | 0.4164 mL | 0.8328 mL | 1.6656 mL | 2.0819 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Sodium 4-pentynoate is an alkynylacetate analogue, which could be incorporated with cellular proteins and utilized as chemical reporter for the profiling of acetylated proteins [1].
Reversible protein acetylation is generally regulated by lysine acetyltransferases (KATs) and lysine deacetylases (KDACs), which play important roles in regulating gene expression and occurrence of disease [1].
The p300-KAT-catalyzed acetylation with histone protein H3 showed that the the 4-pentynoate group can be efficiently transferred onto lysine residue. In jurkat cells, metabolic labeling of sodium 4-pentynoate was in time and dose dependent, which was optimal at 2.5-10 μM of acetate analogs for 6-8 hr. Fluorescent profiling identified 194 of 4-pentynoate labeled proteins from jurkat cells, where 86% of them were identified by radioactive method and 14% was newly identified [1].
Reference:
[1]. Yang Y Y, et al. Bioorthogonal chemical reporters for monitoring protein acetylation. J Am Chem Soc., 2010, 132(11): 3640-3641.
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Bioorthogonal chemical reporters for monitoring protein acetylation.[Pubmed:20192265]
J Am Chem Soc. 2010 Mar 24;132(11):3640-1.
Protein acetylation is a key post-translational modification that regulates diverse biological activities in eukaryotes. Here we report bioorthogonal chemical reporters that enable direct in-gel fluorescent visualization and proteome-wide identification of acetylated proteins via Cu(I)-catalyzed azide-alkyne cycloaddition, often termed "click chemistry". We demonstrate that two alkynyl-acetyl-CoA analogues, 4-pentynoyl-CoA and 5-hexynoyl-CoA, function as efficient substrates of lysine acetyltransferase p300 and serve as sensitive reagents for monitoring p300-catalyzed protein acetylation in vitro. In addition, we demonstrate that three alkynylacetate analogues, sodium 3-butynoate, sodium 4-pentynoate, and sodium 5-hexynoate, can be metabolically incorporated onto cellular proteins through biosynthetic mechanisms for profiling of acetylated proteins in diverse cell types. Mass spectrometry analysis of the enriched 4-pentynoate-labeled proteins revealed many reported as well as new candidate acetylated proteins from Jurkat T cells and specific sites of lysine acetylation. The bioorthogonal chemical reporters described here should serve as powerful tools for investigating protein acetylation.
