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| Other Sizes |
| Targets |
Fmoc-HoPhe-OH targets peptide synthesis applications as a building block for introducing homophenylalanine residues. The extended aromatic side chain (one methylene longer than natural phenylalanine) can influence peptide conformation, hydrophobicity, and biological activity. As a phenylalanine analogue, it is used to study structure-activity relationships and improve peptide drug properties. The base-labile Fmoc group enables SPPS.
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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 activity of Fmoc-HoPhe-OH is primarily as a peptide synthesis building block. The homophenylalanine residue introduced via this compound can modulate peptide conformation and biological activity. Peptides containing homophenylalanine have been studied for various biological activities including enzyme inhibition and receptor modulation. The extended aromatic side chain can enhance hydrophobic interactions with target proteins. The compound itself is not directly biologically active. |
| ln Vivo |
There is no specific in vivo activity data for Fmoc-HoPhe-OH as a standalone compound. Peptides containing homophenylalanine residues synthesized using this building block may be evaluated in vivo for therapeutic applications. The extended aromatic side chain can enhance target binding affinity and improve metabolic stability of peptide drugs. Animal studies would be performed on the final peptide products. Fmoc-HoPhe-OH is a research reagent for peptide synthesis.
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| Enzyme Assay |
In vitro enzyme/receptor binding protocols for Fmoc-HoPhe-OH involve its use in SPPS. Standard Fmoc chemistry: the compound is activated with HATU or HBTU (1 equiv) and DIPEA (2 equiv) in DMF, then coupled to resin-bound peptides. Fmoc deprotection uses 20% piperidine in DMF. Purity is ≥98% by HPLC. Coupling efficiency is monitored by HPLC or Kaiser test. Melting point is 141-159°C. Optical rotation data may be available from suppliers.
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| Cell Assay |
Cell-based protocols are not directly applicable to Fmoc-HoPhe-OH. Homophenylalanine-containing peptides synthesized using this reagent can be tested in cell culture. Peptides are dissolved in DMSO or appropriate buffers, sterile-filtered, and added to cells at 0.1-100 µM. Incubation is for 24-72 hours. Assays include cell viability, proliferation, and specific signaling readouts. The homophenylalanine residue can modulate peptide bioactivity through enhanced hydrophobic interactions.
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| Animal Protocol |
Animal studies with Fmoc-HoPhe-OH are not conducted directly. Peptides containing homophenylalanine residues synthesized using this building block may be evaluated in vivo. Protocols involve administration of the peptide via appropriate routes in animal models. Pharmacokinetic sampling, efficacy assessment, and toxicological evaluation follow standard preclinical study designs. The extended aromatic side chain can improve target binding and peptide stability.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for Fmoc-HoPhe-OH is not applicable as it is a research building block. The compound has molecular weight 401.45 g/mol and formula C₂₅H₂₃NO₄. It has a purity of ≥98% and appears as a white to off-white powder. Store as powder at -20°C. The Fmoc group is removed under basic conditions during peptide synthesis. The resulting homophenylalanine-containing peptides may have altered pharmacokinetics.
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| Toxicity/Toxicokinetics |
Toxicological data for Fmoc-HoPhe-OH is limited. The compound is for research use only. Standard safety precautions should be observed. Store as powder at -20°C for up to 3 years. Acute toxicity is expected to be low. Proper personal protective equipment should be worn when handling. No specific toxicity studies have been reported. It is not intended for human therapeutic use.
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| References | |
| Additional Infomation |
Fmoc-HoPhe-OH (CAS#: 132684-59-4) is also known as Fmoc-L-homophenylalanine, Fmoc-homophenylalanine, and N-α-Fmoc-L-homophenylalanine. Its molecular formula is C₂₅H₂₃NO₄ and molecular weight is 401.45. It is a phenylalanine derivative and standard building block for Fmoc SPPS. It has an extended aromatic side chain compared to phenylalanine. It has no approved therapeutic indications.
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| Molecular Formula |
C25H23NO4
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|---|---|
| Molecular Weight |
401.45442
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| Exact Mass |
401.162
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| CAS # |
132684-59-4
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| PubChem CID |
2761467
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| Appearance |
White to off-white powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
628.3±50.0 °C at 760 mmHg
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| Melting Point |
143 °C
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| Flash Point |
333.8±30.1 °C
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| Vapour Pressure |
0.0±1.9 mmHg at 25°C
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| Index of Refraction |
1.624
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| LogP |
5.89
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
8
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| Heavy Atom Count |
30
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| Complexity |
566
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| Defined Atom Stereocenter Count |
1
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| SMILES |
O=C(O)[C@@H](NC(OCC1C2=CC=CC=C2C3=CC=CC=C31)=O)CCC4=CC=CC=C4
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| InChi Key |
CIHPCIUGLIZADU-QHCPKHFHSA-N
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| InChi Code |
InChI=1S/C25H23NO4/c27-24(28)23(15-14-17-8-2-1-3-9-17)26-25(29)30-16-22-20-12-6-4-10-18(20)19-11-5-7-13-21(19)22/h1-13,22-23H,14-16H2,(H,26,29)(H,27,28)/t23-/m0/s1
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| Chemical Name |
(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-phenylbutanoic acid
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| Synonyms |
Fmoc-HoPhe-OH
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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 | 2.4910 mL | 12.4549 mL | 24.9097 mL | |
| 5 mM | 0.4982 mL | 2.4910 mL | 4.9819 mL | |
| 10 mM | 0.2491 mL | 1.2455 mL | 2.4910 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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