| Size | Price | Stock | Qty |
|---|---|---|---|
| 50mg |
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| 100mg |
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| Other Sizes |
Purity: ≥98%
| Targets |
Alkyl-Chain
L-Azidohomoalanine hydrochloride is a methionine analog that is incorporated into proteins during active protein synthesis in cultured cells. As a PROTAC linker, it does not have a specific biological target itself but serves as a structural component for conjugation. The azide moiety allows for bioorthogonal click chemistry conjugation to alkyne-functionalized molecules. In the context of PROTAC technology, this compound can be used to introduce azide handles into proteins or to link E3 ligase ligands to target protein ligands. |
|---|---|
| ln Vitro |
The E3 ubiquitin ligase ligand and the target protein ligand are the two distinct ligands found in PROTAC, which are joined by a linker. Specifically, target proteins are degraded by PROTAC through the intracellular ubiquitin-proteasome system [1].
In vitro studies demonstrate that L-Azidohomoalanine hydrochloride functions as a click chemistry reagent and methionine analog. The compound can be fed to cultured cells and incorporated into proteins during active protein synthesis, allowing for the labeling and detection of newly synthesized proteins via click chemistry. The azide group allows for efficient conjugation to alkyne-containing molecules via CuAAc click reactions. As a PROTAC linker, it can be used to connect E3 ubiquitin ligase ligands to target protein ligands. In vitro studies typically involve click conjugation of this linker to various ligands, followed by evaluation of the resulting conjugates. |
| ln Vivo |
In vivo activity data for L-Azidohomoalanine hydrochloride as a standalone compound are not reported, as it is utilized as a synthetic linker, click chemistry reagent, or metabolic labeling tool rather than as a therapeutic agent. The compound can be administered to cells or organisms for metabolic labeling studies to track protein synthesis. As a PROTAC linker, the in vivo efficacy of molecules incorporating this linker would depend on the specific target protein ligand and the overall pharmacokinetic properties of the complete construct.
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| Enzyme Assay |
In vitro enzyme/receptor binding assays for L-Azidohomoalanine hydrochloride typically involve click conjugation studies rather than direct binding measurements. The azide group can be conjugated to alkyne-functionalized molecules via CuAAc click reactions, and conjugation efficiency can be assessed by techniques such as NMR spectroscopy, mass spectrometry, or HPLC. In metabolic labeling applications, incorporation of the azido-amino acid into proteins can be detected by click chemistry with fluorescent or biotinylated alkyne probes. The amino acid structure allows for efficient incorporation into proteins by the cellular translation machinery.
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| Cell Assay |
In vitro cell-based assays using L-Azidohomoalanine hydrochloride typically involve metabolic labeling studies. Cells are cultured with the compound, which is incorporated into newly synthesized proteins during active translation. The incorporated azide groups can then be detected by click chemistry with fluorescent or affinity probes, allowing for the visualization and identification of newly synthesized proteins. For PROTAC applications, cells are treated with PROTACs containing this linker, and target protein degradation is measured by Western blotting or immunofluorescence.
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| Animal Protocol |
In vivo animal studies using L-Azidohomoalanine hydrochloride are conducted for metabolic labeling and protein synthesis studies. The compound can be administered to animals to label newly synthesized proteins in vivo, followed by tissue harvesting and detection via click chemistry. For PROTAC applications, studies are conducted as part of the evaluation of complete PROTAC molecules that incorporate this linker. Typical protocols involve administering constructs to animal models, followed by assessment of pharmacokinetics, biodistribution, or efficacy.
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| ADME/Pharmacokinetics |
As a linker and metabolic labeling reagent rather than a therapeutic drug, comprehensive pharmacokinetic data for L-Azidohomoalanine hydrochloride alone are not available. The compound has a molecular formula of C4H9ClN4O2 and a molecular weight of 180.59. The hydrochloride salt form improves aqueous solubility. When used as a PROTAC linker, it contributes to the overall physicochemical properties of the complete construct.
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| Toxicity/Toxicokinetics |
The toxicity profile of L-Azidohomoalanine hydrochloride as an individual compound is not extensively characterized, as it is primarily used as a research reagent. The compound is intended for research use only and is not approved for therapeutic use in humans. Azide-containing compounds can be potentially explosive and should be handled with appropriate safety precautions. Standard laboratory safety practices, including the use of personal protective equipment and handling in a fume hood, are recommended.
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| References | |
| Additional Infomation |
L-Azidohomoalanine hydrochloride (CAS 942518-29-8) has a molecular formula of C4H9ClN4O2 and a molecular weight of 180.59. The compound is an alkyl chain-based PROTAC linker and a click chemistry reagent featuring an azide group. It is also a methionine analog used for metabolic labeling of newly synthesized proteins. The compound is part of the PROTAC linker category and is used in PROTAC synthesis and bioconjugation applications.
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| Molecular Formula |
C4H9CLN4O2
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|---|---|
| Molecular Weight |
180.59
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| Exact Mass |
180.041
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| CAS # |
942518-29-8
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| Related CAS # |
L-Azidohomoalanine;120042-14-0;L-Azidohomoalanine-1,2,3,4-13C4 hydrochloride;2483829-89-4
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| PubChem CID |
46311076
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| Appearance |
White to off-white solid powder
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| LogP |
1.053
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
11
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| Complexity |
163
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| Defined Atom Stereocenter Count |
1
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| SMILES |
[C@@H](N)(C(=O)O)CCN=[N+]=[N-].Cl
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| InChi Key |
MHHYJRIDKLZZEO-DFWYDOINSA-N
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| InChi Code |
InChI=1S/C4H8N4O2.ClH/c5-3(4(9)10)1-2-7-8-6;/h3H,1-2,5H2,(H,9,10);1H/t3-;/m0./s1
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| Chemical Name |
(2S)-2-amino-4-azidobutanoic 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, 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) |
H2O :~125 mg/mL (~692.18 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: 100 mg/mL (553.74 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 | 5.5374 mL | 27.6870 mL | 55.3741 mL | |
| 5 mM | 1.1075 mL | 5.5374 mL | 11.0748 mL | |
| 10 mM | 0.5537 mL | 2.7687 mL | 5.5374 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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