![D-Phenylalanine, N-[N-[(1,1-dimethylethoxy)carbonyl]-L-leucyl]-, phenylmethyl ester](/upload/1124/V68528.png)
| Size | Price | Stock | Qty |
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| 50mg |
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| 100mg |
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| Other Sizes |
| Targets |
As a protected dipeptide building block, this compound does not have direct biological targets. When deprotected and incorporated into larger peptides, the D-Phe residue can interact with targets such as opioid receptors (micro, delta), melanocortin receptors, and neuropeptide receptors. D-Phe also increases resistance to proteases (e.g., chymotrypsin, trypsin), prolonging in vivo half-life. The L-Leu residue provides hydrophobicity. The intermediate itself is classified as a Phenylalanine derivative.
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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].
No in vitro biological activity data are available for this protected dipeptide. It is not tested in cell viability, enzyme inhibition, or receptor binding assays. After deprotection and incorporation into a peptide, the resulting drug candidate may show activity (e.g., IC50 for micro-opioid receptor in the low nM range). No data for the building block. |
| ln Vivo |
No in vivo activity data are available for this building block. Peptides derived from it may be evaluated in animal models (e.g., tail-flick test for analgesia, or tumor growth inhibition in xenografts). The building block itself is not administered.
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| Enzyme Assay |
The compound is not used directly in binding assays. For chemical characterization, HPLC with C18 column, UV detection at 210-254 nm, and mobile phase water/acetonitrile (0.1% TFA) is standard. NMR in CDCl3 confirms structure: Boc group (1.4 ppm), benzyl ester (5.1-5.2 ppm, and 7.3-7.4 ppm), aromatic protons. For peptide synthesis: In SPPS, the dipeptide building block can be incorporated as a pre-formed dipeptide to prevent racemization during coupling. Standard Fmoc-SPPS or Boc-SPPS protocols apply.
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| Cell Assay |
No cell-based protocols are established. For peptides derived from this intermediate, typical assays: opioid receptor binding in HEK293 cells expressing micro-opioid receptor, using [3H]-DAMGO as a radioligand. Cells are incubated with peptide (0.1 nM - 10 uM) for 1 hour at room temperature, filtered, and counted. This building block is not used.
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| Animal Protocol |
No animal studies have been conducted with this building block. For peptides derived from it, typical in vivo studies: mice (C57BL/6) are injected intraperitoneally with peptide (1-30 mg/kg). Analgesia is measured by tail-flick or hot plate test. Blood is collected for plasma stability analysis (LC-MS/MS). No data for the building block.
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| ADME/Pharmacokinetics |
No PK data are available. The compound is not a drug candidate. If administered, the Boc group would be cleaved, and the benzyl ester might be hydrolyzed, yielding the dipeptide L-Leu-D-Phe. This dipeptide could be further hydrolyzed to free amino acids. No ADME studies (half-life, bioavailability) reported. Soluble in DMSO, DMF, and organic solvents. Storage: powder at -20degC.
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| Toxicity/Toxicokinetics |
Safety: May cause skin and eye irritation. Harmful if swallowed (estimated LD50 >2000 mg/kg). Not classified as carcinogen or mutagen. Use standard PPE: gloves, lab coat, safety goggles, fume hood. Avoid inhalation of dust. Stable under recommended storage conditions.
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| References | |
| Additional Infomation |
This compound is not an approved drug and has no clinical trial history. It is a research chemical for peptide synthesis and medicinal chemistry. The dipeptide L-Leu-D-Phe is found in several naturally occurring and synthetic biologically active peptides. The D-Phe residue is common in opioid peptides (e.g., dermorphin, deltorphin) where it confers high potency and receptor selectivity. This building block is the mirror isomer of the Boc-L-Leu-L-Phe-OBzl building block. It is used to prepare peptide analogs with reversed stereochemistry to study structure-activity relationships (SAR) and to enhance proteolytic stability. No approved drugs contain this exact building block. Commercially available for research use only.
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| Molecular Formula |
C27H36N2O5
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| Molecular Weight |
468.585147857666
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| Exact Mass |
468.262
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| CAS # |
159549-96-9
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| PubChem CID |
40586891
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| Appearance |
White to off-white solid powder
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| LogP |
5.4
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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 |
13
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| Heavy Atom Count |
34
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| Complexity |
646
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| Defined Atom Stereocenter Count |
2
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| SMILES |
C(OCC1=CC=CC=C1)(=O)[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CC(C)C)NC(OC(C)(C)C)=O
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| InChi Key |
IKZFNIAMQFYRSM-XZOQPEGZSA-N
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| InChi Code |
InChI=1S/C27H36N2O5/c1-19(2)16-22(29-26(32)34-27(3,4)5)24(30)28-23(17-20-12-8-6-9-13-20)25(31)33-18-21-14-10-7-11-15-21/h6-15,19,22-23H,16-18H2,1-5H3,(H,28,30)(H,29,32)/t22-,23+/m0/s1
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| Chemical Name |
benzyl (2R)-2-[[(2S)-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]amino]-3-phenylpropanoate
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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 | 2.1341 mL | 10.6703 mL | 21.3406 mL | |
| 5 mM | 0.4268 mL | 2.1341 mL | 4.2681 mL | |
| 10 mM | 0.2134 mL | 1.0670 mL | 2.1341 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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