| Size | Price | |
|---|---|---|
| Other Sizes |
| Targets |
Fmoc-D-Phe(4-CF3)-OH is not a drug and does not have a biological target. It is a synthetic building block used in Fmoc solid-phase peptide synthesis (SPPS). The compound is a D-phenylalanine derivative where the phenyl ring is substituted with an electron-withdrawing trifluoromethyl group. The D-configuration and CF3 group enhance the metabolic stability and binding affinity of the resulting peptides by increasing hydrophobic interactions and reducing proteolytic degradation. It is used to study protein-protein interactions.
|
|---|---|
| ln Vitro |
As a chemical synthetic intermediate, Fmoc-D-Phe(4-CF3)-OH does not have inherent in vitro biological activity. Its purpose is as a building block for peptide synthesis. Any biological activity would be associated with the final deprotected peptide synthesized using this derivative. Standard in vitro assays would be performed on the final, fully deprotected peptide, not on this protected intermediate. It is used solely as a reagent for preparing modified peptides with enhanced stability.
|
| ln Vivo |
This compound is not an active pharmaceutical ingredient and does not have in vivo biological activity. It is exclusively a reagent for the chemical synthesis of peptides and peptidomimetics. Any in vivo effects would only be observed after the intermediate has been incorporated into a larger, biologically active molecule and that molecule has been administered to an animal. This intermediate itself is not administered in animal studies. It is used only in chemical synthesis laboratories.
|
| Enzyme Assay |
For non-cell-based assays, this compound is used as a reactant in peptide synthesis. Standard protocols involve dissolving Fmoc-D-Phe(4-CF3)-OH in DMF or DCM. The Fmoc group is removed by treatment with 20% piperidine in DMF for 20 minutes. The identity and purity of the compound are confirmed by HPLC, mass spectrometry, and NMR. For peptide coupling, the free carboxylic acid is activated with HBTU/HOBt or HATU in the presence of DIPEA and then reacted with a resin-bound or solution-phase amine.
|
| Cell Assay |
This chemical intermediate is not used directly in cell-based assays. It is designed as a building block for peptide synthesis. A typical workflow involves coupling this compound to a growing peptide chain on a solid support (e.g., Rink amide resin or Wang resin) using standard Fmoc SPPS protocols. After the full peptide sequence is assembled and deprotected, the peptide is cleaved from the resin, purified by preparative HPLC, and then tested on cells in a functional assay such as receptor binding, enzyme inhibition, or cell proliferation.
|
| Animal Protocol |
This compound is not used in animal experiments. It serves as a synthetic intermediate. For pharmacokinetic or biodistribution studies of a final peptide drug containing the 4-CF3-phenylalanine residue, the radiolabeled version of the drug would be synthesized. The final labeled peptide would then be administered to rodents, and samples would be analyzed by LC-MS/MS to determine its PK profile. The building block itself is never administered.
|
| ADME/Pharmacokinetics |
As a protected amino acid derivative, Fmoc-D-Phe(4-CF3)-OH has a molecular weight of 455.4 g/mol and a molecular formula of C25H20F3NO4. The trifluoromethyl group (CF3) is highly lipophilic and electron-withdrawing, which can alter the pKa of nearby groups and enhance the metabolic stability of the final peptide by blocking oxidative metabolism. The compound is soluble in organic solvents such as DMF, DCM, and DMSO but insoluble in water. Pharmacokinetic studies are not performed on this synthetic intermediate.
|
| Toxicity/Toxicokinetics |
Formal toxicology data is not available for this compound as it is a chemical reagent, not a clinical drug. It is intended for research use only and not for human use. The compound should be handled with care using appropriate personal protective equipment (lab coat, gloves, safety glasses) in a well-ventilated area. Avoid dust formation and inhalation. No specific acute or chronic toxicity data has been determined. It is not a known carcinogen or reproductive hazard.
|
| Additional Infomation |
Fmoc-D-Phe(4-CF3)-OH is a specialized building block for Fmoc solid-phase peptide synthesis (SPPS). The incorporation of a D-amino acid into a peptide increases resistance to proteolytic degradation by proteases, which typically recognize L-amino acids. The trifluoromethyl group is a common bioisostere for a methyl group or a chlorine atom, and it enhances hydrophobic interactions, increasing binding affinity for target proteins. The electron-withdrawing nature of the CF3 group can also modulate the electronic properties of the phenyl ring, influencing pi-pi stacking interactions. This compound is used in the research of peptide inhibitors of protein-protein interactions. It has no clinical applications or approval status.
|
| Molecular Formula |
C25H20F3NO4
|
|---|---|
| Molecular Weight |
455.4258
|
| Exact Mass |
455.134
|
| CAS # |
238742-88-6
|
| PubChem CID |
2777608
|
| Appearance |
White to off-white solid powder
|
| Density |
1.4±0.1 g/cm3
|
| Boiling Point |
619.0±55.0 °C at 760 mmHg
|
| Melting Point |
136-142ºC
|
| Flash Point |
328.2±31.5 °C
|
| Vapour Pressure |
0.0±1.9 mmHg at 25°C
|
| Index of Refraction |
1.588
|
| LogP |
5.98
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
7
|
| Rotatable Bond Count |
7
|
| Heavy Atom Count |
33
|
| Complexity |
670
|
| Defined Atom Stereocenter Count |
1
|
| SMILES |
FC(C1C([H])=C([H])C(=C([H])C=1[H])C([H])([H])[C@]([H])(C(=O)O[H])N([H])C(=O)OC([H])([H])C1([H])C2=C([H])C([H])=C([H])C([H])=C2C2=C([H])C([H])=C([H])C([H])=C12)(F)F
|
| InChi Key |
YMEGJWTUWMVZPD-JOCHJYFZSA-N
|
| InChi Code |
InChI=1S/C25H20F3NO4/c26-25(27,28)16-11-9-15(10-12-16)13-22(23(30)31)29-24(32)33-14-21-19-7-3-1-5-17(19)18-6-2-4-8-20(18)21/h1-12,21-22H,13-14H2,(H,29,32)(H,30,31)/t22-/m1/s1
|
| Chemical Name |
(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[4-(trifluoromethyl)phenyl]propanoic acid
|
| HS Tariff Code |
2934.99.9001
|
| 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)
|
| 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
|
|---|---|
| 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 | 2.1957 mL | 10.9786 mL | 21.9573 mL | |
| 5 mM | 0.4391 mL | 2.1957 mL | 4.3915 mL | |
| 10 mM | 0.2196 mL | 1.0979 mL | 2.1957 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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
