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| Other Sizes |
| Targets |
Z-Met-OH functions primarily as a chemical tool rather than a pharmacologically active drug, thus its "target" is the peptide bond formation process in synthetic chemistry. The compound itself does not target specific biological receptors or enzymes in the classical pharmacological sense. Instead, it serves as a substrate for peptide coupling reagents and a precursor for the incorporation of methionine residues into synthetic peptides. When used in peptide synthesis, the Z-protected amino acid is activated at its carboxylic acid group to form peptide bonds with other amino acid derivatives. The protecting group strategy enables sequential addition of amino acids in a controlled manner, preventing unwanted side reactions during chain elongation. Methionine, the parent compound, is a key component of the methionine cycle, also known as the one-carbon metabolism pathway, which serves as a hub for various metabolic pathways influencing cellular processes ranging from protein synthesis to DNA methylation. As a methionine derivative, Z-Met-OH may be involved in similar biochemical pathways after deprotection. The benzyloxycarbonyl group renders methionine less reactive during chemical reactions, allowing for selective transformations. Environmental factors such as pH, temperature, and the presence of other compounds can affect its stability and interaction with its targets. Heavy metals can interact with sulfur-containing compounds like methionine and its derivatives, potentially affecting their stability and function.
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| ln Vitro |
Commercial ergot supplements have been made from amino acids and their derivatives. They affect the release of anabolic hormones, the availability of fuel for activity, the ability to think clearly under pressure, and the prevention of muscular damage brought on by exertion. They are regarded as advantageous synergistic food ingredients [1].
The in vitro activity of Z-Met-OH is evaluated primarily through its performance in peptide coupling reactions rather than biological assays. In standard solution-phase peptide synthesis, the compound demonstrates high coupling efficiency (typically >95%) when activated with reagents such as DCC (dicyclohexylcarbodiimide), HATU (1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate), or other carbodiimide-based coupling agents. Its reactivity is characterized by the successful formation of peptide bonds with various amino acid esters and amides under mild conditions, typically at room temperature for 1-4 hours. The Z-protecting group remains stable under acidic conditions but is cleaved by catalytic hydrogenation (H₂/Pd-C) or treatment with HBr in acetic acid. Quality control assessments include HPLC purity analysis (typically ≥98%) and optical rotation measurements ([α]²⁵/D -18.5° in 95% ethanol). In coupling reactions, the compound is typically used at 1.0 equivalent with 1.1 equivalents of coupling reagent and 2 equivalents of base (such as DIEA or TEA) in solvents like DMF or dichloromethane. Reaction progress is monitored by TLC, and the product is isolated by extraction and purified by column chromatography or recrystallization. The compound shows no intrinsic biological activity in cell-free systems as it is strictly a synthetic intermediate. |
| ln Vivo |
In vivo activity is not applicable to Z-Met-OH as this compound is not intended for administration to living organisms. It is exclusively a research chemical and synthetic intermediate used exclusively in laboratory settings for peptide preparation. The compound is not designed for therapeutic or diagnostic purposes in animal models. Any biological activity that might be observed would be a result of metabolic conversion following deprotection, but such studies are not typically conducted with this protected amino acid. Its utility lies entirely in the chemical synthesis domain rather than in pharmacological evaluation. The compound is stored and handled under standard laboratory conditions for chemical synthesis, typically at 2-8°C, and is not formulated for any route of administration. While methionine itself is an essential amino acid with known in vivo functions, the protected Z-Met-OH form would require deprotection to liberate free methionine before any biological activity could be manifested. No established animal models or in vivo efficacy studies exist for this compound.
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| Enzyme Assay |
The in vitro enzyme/receptor binding (non-cellular) experimental workflow for Z-Met-OH involves standard peptide synthesis and characterization procedures. Typically, the compound (1.0 equivalent) is dissolved in an appropriate solvent such as DMF or dichloromethane, and a coupling reagent (e.g., HATU or DCC, 1.1 equivalents) along with a base (e.g., DIEA, 2 equivalents) is added. The reaction mixture is stirred at room temperature for 1-4 hours, and progress is monitored by TLC. After completion, the product is isolated by extraction and purified by column chromatography or recrystallization. Characterization includes ¹H-NMR, ¹³C-NMR, and mass spectrometry to confirm structure. The synthetic route involves the reaction of L-methionine with benzyloxycarbonyl chloride (Cbz-Cl) in the presence of a base such as sodium hydroxide or triethylamine. The reaction is usually carried out in an organic solvent like dichloromethane or tetrahydrofuran at low temperatures to prevent side reactions. HPLC purity (≥98%) and optical rotation measurements are used for quality control. The compound's XLogP3 value is 2.1, indicating moderate lipophilicity, with 2 hydrogen bond donors and 5 hydrogen bond acceptors.
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| Cell Assay |
In vitro cell-based experimental workflows are not typically performed with Z-Met-OH, as the compound is not intended for biological activity screening. However, when used as a precursor in peptide synthesis, the resulting peptides may be subjected to cell-based assays. In such cases, Z-Met-OH would first be deprotected to liberate free methionine or incorporated into a peptide sequence, and the final peptide product would be tested in appropriate cell lines. For methionine-containing peptides, typical assays might include cell viability (MTT assay), apoptosis detection (Annexin V staining), or receptor binding studies depending on the biological target of the synthesized peptide. Cells are typically cultured in DMEM with 10% FBS, treated with peptide concentrations ranging from 0.1 to 100 µM for 24-72 hours, and read by plate reader or flow cytometry. The protected amino acid itself is not directly tested in these systems as it would not be expected to interact with cellular targets in its protected form.
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| Animal Protocol |
In vivo animal experimental workflows are not applicable to Z-Met-OH. This compound is exclusively a synthetic intermediate and research chemical, not a drug candidate intended for animal testing. There are no established animal models or in vivo protocols associated with this protected amino acid. Any in vivo studies would involve the final deprotected peptide products rather than the protected intermediate itself. The compound is stored and handled under standard laboratory conditions for chemical synthesis, typically at 2-8°C. Industrial production follows similar synthetic routes but on a larger scale, using automated peptide synthesizers and large-scale reactors to ensure high yield and purity. Reaction conditions are optimized to minimize impurities and maximize product quality.
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| ADME/Pharmacokinetics |
The pharmacokinetic properties of Z-Met-OH have not been characterized, as the compound is not intended for pharmaceutical use. Being a protected amino acid derivative with a molecular weight of 283.35 g/mol and LogP of 2.1, it would be expected to have moderate lipophilicity if it were administered. However, the Z-protecting group would likely be cleaved metabolically, and any pharmacokinetic data would pertain to the liberated methionine rather than the parent compound. Methionine, the parent compound, is known to be absorbed in the small intestine and transported to the liver, where it is metabolized. The compound is stable under recommended storage conditions (2-8°C) and is not designed for systemic exposure in living organisms. No data on absorption, distribution, metabolism, or excretion are available for the protected form. The compound's XLogP3 value of 2.1 suggests it would have moderate membrane permeability if administered, but this is purely speculative as the compound is not intended for in vivo use.
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| Toxicity/Toxicokinetics |
Toxicological data for Z-Met-OH are limited as it is not a pharmaceutical agent. Standard safety precautions apply when handling this chemical: it may cause skin and eye irritation, and inhalation of dust should be avoided. The compound should be handled in a fume hood with appropriate personal protective equipment including gloves, safety glasses, and laboratory coat. No chronic toxicity, carcinogenicity, or reproductive toxicity studies have been conducted, as these are not relevant for a synthetic intermediate. The compound is intended for research use only and is not approved for human or veterinary applications. It is not classified as a hazardous substance under most regulatory frameworks, but standard laboratory chemical safety practices should be followed. The compound is stable under normal handling conditions and does not present acute toxicity concerns based on its chemical structure as a protected amino acid.
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| References |
[1]. Luckose F, et al. Effects of amino acid derivatives on physical, mental, and physiological activities. Crit Rev Food Sci Nutr. 2015;55(13):1793-1144.
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| Additional Infomation |
Z-Met-OH is a well-established reagent in peptide chemistry, commercially available from multiple suppliers. It is a standard building block for introducing methionine residues in peptide synthesis. The Z protecting group was first introduced by Bergmann and Zervas in 1932 and remains one of the most widely used amino protecting groups in organic synthesis. This compound serves as a key intermediate in the preparation of various bioactive peptides and pharmaceutical compounds. It is not a drug and has not undergone clinical trials or received regulatory approval. The compound is used in studies involving protein synthesis and modification, particularly in the investigation of methionine's role in biological systems. Its benzyloxycarbonyl protecting group provides stability and ease of removal under mild conditions, making it a preferred choice for many synthetic applications. The compound can be synthesized through the protection of the amino group of L-methionine with benzyloxycarbonyl chloride in the presence of a base. Industrial production follows similar synthetic routes but on a larger scale. The compound is available in various pack sizes and purity grades for research applications.
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| Molecular Formula |
C13H17NO4S
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|---|---|
| Molecular Weight |
283.34
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| Exact Mass |
283.087
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| CAS # |
1152-62-1
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| PubChem CID |
1550857
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| Appearance |
White to off-white solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
504.7±50.0 °C at 760 mmHg
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| Melting Point |
67-69 °C
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| Flash Point |
259.0±30.1 °C
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| Vapour Pressure |
0.0±1.4 mmHg at 25°C
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| Index of Refraction |
1.567
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| LogP |
2.77
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
8
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| Heavy Atom Count |
19
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| Complexity |
292
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| Defined Atom Stereocenter Count |
1
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| SMILES |
CSCC[C@@H](C(=O)O)NC(=O)OCC1=CC=CC=C1
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| InChi Key |
FPKHNNQXKZMOJJ-NSHDSACASA-N
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| InChi Code |
InChI=1S/C13H17NO4S/c1-19-8-7-11(12(15)16)14-13(17)18-9-10-5-3-2-4-6-10/h2-6,11H,7-9H2,1H3,(H,14,17)(H,15,16)/t11-/m0/s1
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| Chemical Name |
(2S)-4-methylsulfanyl-2-(phenylmethoxycarbonylamino)butanoic 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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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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 | 3.5293 mL | 17.6466 mL | 35.2933 mL | |
| 5 mM | 0.7059 mL | 3.5293 mL | 7.0587 mL | |
| 10 mM | 0.3529 mL | 1.7647 mL | 3.5293 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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