| Size | Price | Stock | Qty |
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| 5g |
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| Other Sizes |
| Targets |
As a synthetic intermediate, (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(3-cyanophenyl)propanoic acid has no specific biological target. Its role is to provide 3-cyanophenylalanine residues in peptide chains. The Fmoc protecting group enables standard Fmoc solid-phase peptide synthesis (SPPS) workflows, allowing for the controlled assembly of peptide chains. The cyano group at the meta position of the phenyl ring introduces unique electronic and steric properties that can significantly alter the peptide's physicochemical properties and biological activity compared to unsubstituted phenylalanine. The compound does not interact with enzymes or receptors in pharmacological assays. Its "target" is the peptide coupling reaction, where it acts as a protected amino acid donor. This compound is particularly valuable in the synthesis of peptides and peptidomimetics where the incorporation of non-natural amino acids with modified aromatic rings is desired for structure-activity relationship studies.
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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 (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(3-cyanophenyl)propanoic acid is measured by coupling efficiency in solid-phase peptide synthesis (SPPS). Typically, it is coupled to resin-bound amine using standard Fmoc-SPPS conditions: deprotection of the resin-bound Fmoc group with 20% piperidine in DMF, followed by coupling with the compound (typically 3-5 equivalents) using coupling reagents such as HATU, HBTU, or DIC with HOBt, and DIEA as base. The coupling reaction is typically performed at room temperature for 1-4 hours. Coupling efficiency is monitored by the Kaiser test (ninhydrin test) or by quantitative HPLC. Cleavage and deprotection with TFA/TIS/H₂O yield the desired peptide. Purity is typically ≥97%. No inherent biological activity is observed as the compound is a protected amino acid derivative. Amino acids and amino acid derivatives have been commercially used as ergogenic supplements. |
| ln Vivo |
In vivo activity is not applicable for (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(3-cyanophenyl)propanoic acid. The compound is not used in animals and is a research chemical for laboratory synthesis only. It is not intended for therapeutic or diagnostic purposes. 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.
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| Enzyme Assay |
The in vitro enzyme/receptor binding (non-cellular) experimental workflow for (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(3-cyanophenyl)propanoic acid involves standard Fmoc solid-phase peptide synthesis procedures. Standard SPPS cycle: deprotect Fmoc with 20% piperidine in DMF (typically 2 × 5-10 minutes), wash with DMF, couple the compound (3 equiv.) with HATU (2.9 equiv.) and DIEA (6 equiv.) for 1-2 hours, wash, repeat. After complete assembly of the peptide sequence, the peptide is cleaved from the resin and deprotected using a cleavage cocktail containing TFA, TIS, and water (typically 95:2.5:2.5) for 2-4 hours. The crude peptide is precipitated with cold ether, and the product is analyzed by HPLC-MS. The compound's SMILES is OC(=O)[C@H](Cc1cccc(c1)C#N)NC(=O)OCC1c2ccccc2-c2ccccc12.
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| Cell Assay |
In vitro cell-based experimental workflows are not performed on this intermediate. The final deprotected peptides may be tested in cell-based assays, but the protected compound itself is not used. When the final deprotected peptide is tested, 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.
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| Animal Protocol |
In vivo animal experiments are not applicable for (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(3-cyanophenyl)propanoic acid. The compound is stored at -20°C for powder and -80°C for solvent. The compound is not formulated for any route of administration. Any in vivo studies would involve the final deprotected peptide products rather than the protected amino acid itself.
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| ADME/Pharmacokinetics |
The pharmacokinetic properties of (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(3-cyanophenyl)propanoic acid have not been characterized. The compound is not a drug. No ADME data are available. The compound is stable under recommended storage conditions: powder at -20°C for up to 3 years or at 4°C for up to 2 years; in solvent at -80°C for up to 1 year. If administered, the Fmoc protecting group would likely be cleaved metabolically, releasing the free amino acid, but such studies are not conducted with this protected amino acid.
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| Toxicity/Toxicokinetics |
The toxicological data for (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(3-cyanophenyl)propanoic acid are not well-documented. Standard laboratory safety practices should be followed. The compound is intended for research use only and is not approved for human or veterinary applications. No chronic toxicity, carcinogenicity, or reproductive toxicity studies have been conducted, as these are not relevant for a synthetic intermediate.
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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):1793-955.
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| Additional Infomation |
(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(3-cyanophenyl)propanoic acid is a phenylalanine derivative used as a building block in Fmoc-based solid-phase peptide synthesis. The cyano group at the meta position introduces unique electronic and steric properties that can significantly alter peptide conformation and biological activity. The compound is a useful organic compound for life sciences research. It is not a drug and has no clinical trials or approvals. The compound is available from multiple suppliers with purity typically ≥97%. The product is for research use only. The SMILES is OC(=O)[C@H](Cc1cccc(c1)C#N)NC(=O)OCC1c2ccccc2-c2ccccc12.
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| Molecular Formula |
C25H20N2O4
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|---|---|
| Molecular Weight |
412.44
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| Exact Mass |
412.142
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| CAS # |
205526-36-9
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| PubChem CID |
6957990
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| Appearance |
White to off-white solid powder
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| Density |
1.35 g/cm3
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| Boiling Point |
670.7ºC at 760 mmHg
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| Melting Point |
115.6 °C
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| Flash Point |
359.5ºC
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| Vapour Pressure |
6.61E-19mmHg at 25°C
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| Index of Refraction |
1.672
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| LogP |
4.483
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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 |
7
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| Heavy Atom Count |
31
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| Complexity |
679
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| Defined Atom Stereocenter Count |
1
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| SMILES |
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@@H](CC4=CC(=CC=C4)C#N)C(=O)O
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| InChi Key |
CVLOUTPKZUJTGV-QHCPKHFHSA-N
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| InChi Code |
InChI=1S/C25H20N2O4/c26-14-17-7-5-6-16(12-17)13-23(24(28)29)27-25(30)31-15-22-20-10-3-1-8-18(20)19-9-2-4-11-21(19)22/h1-12,22-23H,13,15H2,(H,27,30)(H,28,29)/t23-/m0/s1
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| Chemical Name |
(2S)-3-(3-cyanophenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)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) |
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 | 2.4246 mL | 12.1230 mL | 24.2460 mL | |
| 5 mM | 0.4849 mL | 2.4246 mL | 4.8492 mL | |
| 10 mM | 0.2425 mL | 1.2123 mL | 2.4246 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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