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| 1g | ||
| Other Sizes |
| Targets |
Z-Val-Ala-OH does not have a specific biological target as a drug, as its primary utility is as a chemical building block. However, the Val-Ala dipeptide sequence represents a recognized cleavage site for multiple protease classes, including thermolysin in enzymatic synthesis cascades and DPPIV/CD26 in prodrug activation pathways. The compound has been demonstrated as a functional carboxyl component in thermolysin-catalyzed synthesis, where the enzyme accepts Z-protected dipeptides of general formula Z-A1-A2-OH. Its value lies in its chemical properties as a synthetic intermediate for constructing peptides.
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| ln Vitro |
Z-Val-Ala-OH does not exhibit pharmacological activity in vitro. As a protected dipeptide derivative, it is a synthetic intermediate rather than a bioactive compound. In vitro studies using this compound focus on its chemical reactivity in peptide synthesis and its role as a substrate for specific proteases like thermolysin and DPPIV/CD26. It is a useful reagent in the preparation and biological evaluation of peptide amide conjugates of nucleosides as prodrugs that are converted to parent drugs by the action of DPPIV/CD26. It does not bind to receptors or inhibit enzymes in a pharmacological sense.
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| ln Vivo |
Z-Val-Ala-OH is not a pharmacologically active compound and therefore does not have defined in vivo activity as a drug. When administered to animals as part of a prodrug, the Z-protected dipeptide would likely be recognized and cleaved by enzymes such as DPPIV/CD26 to release the active drug. However, the compound itself is not used therapeutically. Its primary value remains in synthetic chemistry, where it serves as a building block for the preparation of peptides and pharmaceutical compounds.
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| Enzyme Assay |
In vitro enzyme assays for Z-Val-Ala-OH are primarily focused on studying protease activity. A standard protocol involves incubating the compound with an enzyme preparation, such as thermolysin or DPPIV/CD26, in a suitable buffer at physiological pH and temperature. The hydrolysis of the dipeptide bond releases valine and alanine derivatives, which can be quantified by HPLC or mass spectrometry. The progress of the reaction can be monitored, and kinetic parameters such as Km and Vmax can be determined. These assays are used to characterize the substrate specificity of proteases and to screen for enzyme inhibitors.
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| Cell Assay |
In vitro cellular assays using Z-Val-Ala-OH are limited due to the compound's role as a synthetic intermediate rather than a bioactive molecule. However, it can be used in cell culture studies to investigate the delivery of peptide prodrugs. Cells are cultured in media supplemented with the compound, and its uptake and enzymatic cleavage are monitored. The effects of the released active drug can be assessed. These experiments are typically conducted in cell lines that express relevant proteases like DPPIV/CD26.
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| Animal Protocol |
In vivo animal studies with Z-Val-Ala-OH are not typically conducted for the compound itself, as it is a synthetic intermediate. However, it may be used as a prodrug component in animal models to study drug delivery and activation. A typical protocol would involve administering the compound or a peptide conjugate containing this sequence to rodents via oral or intravenous routes. Blood samples are collected to measure drug levels, and the efficacy of the released drug is assessed. These studies help to evaluate the utility of Z-protected dipeptides as prodrug moieties.
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| ADME/Pharmacokinetics |
As a protected dipeptide, Z-Val-Ala-OH is not a drug candidate and specific pharmacokinetic data are not available. If administered in vivo as part of a prodrug, the compound would likely be cleaved by proteases to release the active drug and the dipeptide components. The Z-protecting group is typically stable under physiological conditions until enzymatic or chemical removal is intended. The compound's pharmacokinetic properties would be determined by the rate of its cleavage and the subsequent metabolism of its components.
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| Toxicity/Toxicokinetics |
The compound is generally considered to have low toxicity, consistent with its use as a chemical reagent. It is a protected dipeptide composed of two natural amino acids and a Z-protecting group, which is commonly used in peptide synthesis. Standard laboratory safety precautions, including the use of personal protective equipment, are recommended. It is not classified as a highly toxic substance, but appropriate safety measures should be followed. Inhalation, ingestion, or skin contact should be avoided.
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| References | |
| Additional Infomation |
Z-Val-Ala-OH (Carbobenzoxy-L-valyl-L-alanine, CAS 24787-89-1) is a protected dipeptide building block used in peptide synthesis. Its molecular formula is C₁₆H₂₂N₂O₅ and its molecular weight is 322.36 g/mol. The Z (benzyloxycarbonyl) group provides orthogonal protection for the N-terminus. The Val-Ala sequence is a recognized cleavage site for enzymes like thermolysin and DPPIV/CD26, making it useful in prodrug design. It is intended for research use only and is not for human therapeutic applications.
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| Molecular Formula |
C16H22N2O5
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|---|---|
| Molecular Weight |
322.3563
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| Exact Mass |
322.153
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| CAS # |
24787-89-1
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| PubChem CID |
7020631
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| Appearance |
White to off-white solid powder
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| Density |
1.13g/cm3
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| Boiling Point |
513.5ºC at 760mmHg
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| Flash Point |
264.4ºC
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| LogP |
2.308
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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 |
8
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| Heavy Atom Count |
23
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| Complexity |
419
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| Defined Atom Stereocenter Count |
2
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| SMILES |
C[C@@H](C(=O)O)NC(=O)[C@H](C(C)C)NC(=O)OCC1=CC=CC=C1
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| InChi Key |
KDQLNJPBTLIYNW-AAEUAGOBSA-N
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| InChi Code |
InChI=1S/C16H22N2O5/c1-10(2)13(14(19)17-11(3)15(20)21)18-16(22)23-9-12-7-5-4-6-8-12/h4-8,10-11,13H,9H2,1-3H3,(H,17,19)(H,18,22)(H,20,21)/t11-,13-/m0/s1
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| Chemical Name |
(2S)-2-[[(2S)-3-methyl-2-(phenylmethoxycarbonylamino)butanoyl]amino]propanoic acid
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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 |
| 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 (~310.21 mM)
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|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.1021 mL | 15.5106 mL | 31.0212 mL | |
| 5 mM | 0.6204 mL | 3.1021 mL | 6.2042 mL | |
| 10 mM | 0.3102 mL | 1.5511 mL | 3.1021 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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