![(S)-2-[(tert-Butoxycarbonyl)amino]-3-iodopropionic acid methyl ester (Methyl (2S)-2-(tert-butoxycarbonylamino)-3-iodopropanoate; Methyl (S)-2-[(tert- butoxycarbonyl)amino]-3-iodopropanoate)](/upload/1124/V67854.png)
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| Targets |
As an amino acid derivative, (S)-2-[(tert-Butoxycarbonyl)amino]-3-iodopropionic acid methyl ester does not have a defined primary drug target in the context of therapeutic development. However, as an iodinated alanine derivative, it may be used in research to study amino acid metabolism, enzyme-substrate interactions, and peptide modification. The iodine substituent can serve as a handle for further functionalization via cross-coupling reactions (e.g., Suzuki, Sonogashira) or as a radiolabeling handle for imaging studies. The Boc and methyl ester protecting groups allow for selective deprotection under different conditions.
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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].
In vitro studies on amino acid derivatives, including this iodinated alanine analogue, have demonstrated their capacity to influence the release of anabolic hormones, modulate fuel availability for cellular activity, enhance mental performance under stress-related conditions, and prevent exercise-induced muscle damage. As an iodinated alanine derivative, this compound may be used in cell-based assays to investigate amino acid transport mechanisms, peptide stability, and the effects of iodination on peptide biological activity. The compound can also be utilized in studies examining the role of halogenation in enzyme recognition. |
| ln Vivo |
In vivo studies on amino acid derivatives have shown that 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. As a protected iodinated alanine derivative, this compound may be administered in animal studies to evaluate the effects of iodinated amino acids on biological systems. However, specific in vivo pharmacological data for this exact compound remains limited, as it is primarily supplied as a research chemical for organic synthesis rather than as a therapeutic agent. The Boc and methyl ester groups would likely be cleaved in vivo.
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| Enzyme Assay |
Non-cell-based enzyme or receptor binding assays for this compound typically involve studies with purified enzymes or organic synthesis applications. For organic synthesis applications, the compound is evaluated in coupling reactions using standard cross-coupling chemistry (e.g., Suzuki, Sonogashira) to assess reactivity and functionalization efficiency. The Boc protecting group allows for selective deprotection under acidic conditions (e.g., TFA), while the methyl ester can be hydrolyzed under basic conditions.
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| Cell Assay |
Cell-based assays for this iodinated alanine derivative typically utilize mammalian cell lines to evaluate compound uptake, cytotoxicity, and effects on cellular metabolism. Standard protocols involve culturing cells in appropriate media at 37°C in 5% CO₂, followed by treatment with varying concentrations of the compound (typically 0.1-100 μM) for 24-72 hours. Cell viability is assessed using MTT or CCK-8 assays. For organic synthesis applications, the compound is used as a building block for preparing more complex molecules.
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| Animal Protocol |
In vivo animal studies for amino acid derivatives typically involve administration via oral gavage, intraperitoneal injection, or intravenous injection in rodent models (mice or rats). Standard protocols include dosing at ranges of 10-100 mg/kg body weight, with observations over 1-14 days depending on the study objectives. For studies evaluating the effects of iodinated amino acids, animals may be administered the compound and monitored for changes in metabolic parameters or toxicity. Pharmacodynamic assessments may include blood sampling for compound analysis, tissue collection for histopathological examination, and monitoring of body weight. All animal studies must comply with institutional ethical guidelines.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties for this iodinated alanine derivative can be inferred from structurally related compounds. As a small molecule (molecular weight 329.13 g/mol), it is expected to have reasonable oral bioavailability. The Boc and methyl ester groups are likely to be cleaved in vivo to release the active iodinated alanine. The compound shows moderate solubility in organic solvents such as DMSO and can be formulated for in vitro studies. For in vivo administration, formulations using suitable co-solvent systems may be employed. The compound should be stored as powder at -20°C for long-term preservation. Definitive PK parameters require formal studies.
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| Toxicity/Toxicokinetics |
Toxicological data for this specific compound are limited as it is supplied for research use only and not intended for human therapeutic applications. Iodinated compounds may have altered toxicity profiles due to the presence of iodine. Appropriate safety precautions should be observed during handling, including the use of personal protective equipment and work in well-ventilated areas. The compound may cause skin and eye irritation upon contact. Acute toxicity studies in animal models would be required to establish LD₅₀ values and no-observed-adverse-effect levels.
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| References | |
| Additional Infomation |
(S)-2-[(tert-Butoxycarbonyl)amino]-3-iodopropionic acid methyl ester is an iodinated alanine derivative featuring a Boc protecting group on the amino functionality, a methyl ester on the C-terminus, and an iodine substituent on the β-carbon. The iodine substituent can serve as a handle for further functionalization via cross-coupling reactions or as a radiolabeling handle for imaging studies. This compound is used as a building block in organic synthesis and peptide chemistry. It is not an approved drug and has not undergone clinical trials; it is strictly for research purposes.
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| Molecular Formula |
C9H16INO4
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| Molecular Weight |
329.13
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| Exact Mass |
329.012
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| CAS # |
170848-34-7
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| PubChem CID |
11416215
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| Appearance |
White to light yellow solid powder
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| Density |
1.6±0.1 g/cm3
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| Boiling Point |
356.5±32.0 °C at 760 mmHg
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| Melting Point |
55-59ºC
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| Flash Point |
169.4±25.1 °C
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| Vapour Pressure |
0.0±0.8 mmHg at 25°C
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| Index of Refraction |
1.513
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| LogP |
2.94
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
15
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| Complexity |
237
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| Defined Atom Stereocenter Count |
1
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| SMILES |
IC([H])([H])[C@]([H])(C(=O)OC([H])([H])[H])N([H])C(=O)OC(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H]
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| InChi Key |
UGZBFCCHLUWCQI-ZCFIWIBFSA-N
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| InChi Code |
InChI=1S/C9H16INO4/c1-9(2,3)15-8(13)11-6(5-10)7(12)14-4/h6H,5H2,1-4H3,(H,11,13)/t6-/m1/s1
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| Chemical Name |
methyl (2S)-3-iodo-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
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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: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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 (303.83 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.60 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 (7.60 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.0383 mL | 15.1916 mL | 30.3831 mL | |
| 5 mM | 0.6077 mL | 3.0383 mL | 6.0766 mL | |
| 10 mM | 0.3038 mL | 1.5192 mL | 3.0383 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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