| Size | Price | Stock | Qty |
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| 50mg |
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| 100mg |
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| Other Sizes |
| Targets |
Not applicable as a therapeutic target. PrK is a non-canonical amino acid designed to be recognized and incorporated into proteins by specific aminoacyl-tRNA synthetases (specifically, wild-type Methanococcus mazei PyIRS) for subsequent bioorthogonal labeling. [1]
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|---|---|
| ln Vitro |
Using click chemistry H3 variant H3.3 molecular hyperspectral SRS imaging, label cellular proteins that carry N-ε-propargyloxycarbonyl-L-lysine (HL-Lys(Poc)-OH) hydrochloride, such as histones, Sec61β, and Htt74Q, with sensitive Raman tags [1].
PrK can be site-specifically incorporated into proteins in E. coli and mammalian cells using the genetic code expansion technique. Once incorporated, the alkyne group of PrK enables bio-conjugation of fluorescent probes via copper-catalyzed azide-alkyne cycloaddition (CuAAC) for protein visualization. [1] This labeling scheme has been applied for super-resolution microscopy imaging of target proteins after cell fixation. [1] PrK-based labeling has also been used in hyperspectral stimulated Raman scattering (SRS) microscopy. Cellular proteins carrying PrK (e.g., Sec61β, Htt74Q, histone H3.3) were labeled with a sensitive Raman tag via click chemistry for molecular hyperspectral SRS imaging. [1] |
| ln Vivo |
PrK has been used for bio-conjugation of fluorescent probes in living animals (the specific animal model is not detailed in the text), demonstrating the in vivo applicability of the labeling technique. [1]
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| Cell Assay |
For labeling proteins in live mammalian cells, a plasmid encoding the target protein with an amber (TAG) mutation at the desired site, along with plasmids encoding the MmPyIRS/tRNAPylCUA pair, are transfected into cells. The cells are cultured in medium supplemented with PrK. After expression of the target protein containing PrK, cells are washed and incubated with an azide-functionalized fluorescent dye in the presence of a CuAAC reaction cocktail (containing CuSO4, a reducing agent like sodium ascorbate, and a stabilizing ligand). Following the click reaction, cells are washed thoroughly to remove excess dye and then imaged or fixed for further analysis (e.g., super-resolution microscopy). [1]
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| References | |
| Additional Infomation |
Propynolysine (PrK) is a non-natural lysine amino acid (UAA) with a propynoyloxycarbonyl side chain. Its key feature is the alkynyl group, which can be used as a bio-orthogonal chemical marker. [1]
Due to its simple synthesis and efficient incorporation into proteins by the pyrolysyl-tRNA synthetase/tRNA pair of wild-type methanococcus mazei, it is widely used. [1] Its main application is site-specific protein labeling via CuAAC "click chemistry" for imaging and biochemical analysis of various organisms, from bacteria to animals. [1] |
| Molecular Formula |
C10H17CLN2O4
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|---|---|
| Molecular Weight |
264.705981969833
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| Exact Mass |
264.088
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| CAS # |
1428330-91-9
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| PubChem CID |
118898827
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| Appearance |
White to off-white solid powder
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| LogP |
1.821
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
8
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| Heavy Atom Count |
17
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| Complexity |
282
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| Defined Atom Stereocenter Count |
1
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| SMILES |
C#CCOC(=O)NCCCC[C@@H](C(=O)O)N.Cl
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| InChi Key |
ZYUXGVUWYHHZTD-QRPNPIFTSA-N
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| InChi Code |
InChI=1S/C10H16N2O4.ClH/c1-2-7-16-10(15)12-6-4-3-5-8(11)9(13)14;/h1,8H,3-7,11H2,(H,12,15)(H,13,14);1H/t8-;/m0./s1
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| Chemical Name |
(2S)-2-amino-6-(prop-2-ynoxycarbonylamino)hexanoic acid;hydrochloride
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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 Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| 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 : ~100 mg/mL (~377.77 mM)
H2O : ≥ 100 mg/mL (~377.77 mM) |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (9.44 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 25.0 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: ≥ 2.5 mg/mL (9.44 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 25.0 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: ≥ 2.5 mg/mL (9.44 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 | 3.7777 mL | 18.8886 mL | 37.7772 mL | |
| 5 mM | 0.7555 mL | 3.7777 mL | 7.5554 mL | |
| 10 mM | 0.3778 mL | 1.8889 mL | 3.7777 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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