![L-Phenylalanine, N-[N-[(1,1-dimethylethoxy)carbonyl]-D-leucyl]-, phenylmethyl ester](/upload/1124/V68377.png)
| Size | Price | Stock | Qty |
|---|---|---|---|
| 50mg |
|
||
| 100mg |
|
||
| Other Sizes |
| Targets |
As a protected dipeptide intermediate, L-Phenylalanine, N-[N-[(1,1-dimethylethoxy)carbonyl]-D-leucyl]-, phenylmethyl ester has no direct biological target. When deprotected and incorporated into larger peptides or drugs, the L-Phe residue can target opioid receptors, neuropeptide receptors, or enzyme active sites. The D-Leu residue may confer resistance to proteases, prolonging half-life. However, the intermediate itself is inert. It is classified as a Phenylalanine Derivative.
|
|---|---|
| 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 dipeptide building block. It is not used in cell viability, enzyme inhibition, or receptor binding assays as a test article. Any activity would be associated with the final deprotected peptide drug candidate. For example, a peptide containing D-Leu-L-Phe may show enhanced stability in serum compared to all-L peptides. |
| ln Vivo |
No in vivo activity data are available. The compound has not been administered to animals. Peptides assembled using this building block may be evaluated in vivo for therapeutic efficacy (e.g., in cancer, inflammation, or pain models), but no such data exist for the building block.
|
| Enzyme Assay |
The compound is not used in enzyme/receptor binding assays. For chemical analysis, standard HPLC with a C18 column, UV detection at 210-254 nm, and mobile phase water/acetonitrile (0.1% TFA) are used. NMR in CDCl3 or DMSO-d₆ confirms structure. For solubility, the compound is soluble in DMSO and DMF but poorly soluble in water. No biological assays are performed.
|
| Cell Assay |
No cell-based protocols are established for this intermediate. In peptide synthesis, typical solution-phase coupling: The compound can be deprotected (Boc removal with 25% TFA in DCM) to yield H-D-Leu-Phe-OBzl, which can then be further coupled with additional amino acids. Alternatively, the benzyl ester can be removed by hydrogenation (H2, Pd/C in methanol). The resulting free acid or free amine can be used in subsequent couplings. The intermediate itself is not added to cell culture.
|
| Animal Protocol |
No animal studies have been conducted with this protected dipeptide. For downstream peptides, in vivo efficacy might be evaluated in xenograft or disease models (e.g., tumor-bearing mice treated with peptide-drug conjugates). The building block is not administered.
|
| ADME/Pharmacokinetics |
No pharmacokinetic data are available. The compound is not a drug candidate. If administered, both the Boc and OBzl protecting groups would likely be removed by metabolic enzymes, yielding the dipeptide D-Leu-L-Phe, which would then be hydrolyzed into free D-leucine and L-phenylalanine. No ADME studies have been reported. Storage: powder at -20degC stable for years.
|
| 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, goggles, lab coat, fume hood). Avoid inhalation of dust. In case of contact, flush with water. The compound is stable as a solid under dry, cool conditions.
|
| 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):1793-878.
|
| Additional Infomation |
L-Phenylalanine, N-[N-[(1,1-dimethylethoxy)carbonyl]-D-leucyl]-, phenylmethyl ester is not an approved drug and has no clinical trial history. It is a research chemical for peptide synthesis and medicinal chemistry. The dipeptide sequence D-Leu-L-Phe is found in various biologically active peptides and may serve as a model for studying stereochemical effects on receptor binding and enzymatic stability. This compound is distinct from its stereoisomer (containing L-Leu-L-Phe, CAS 70637-26-2). The D-Leu-L-Phe sequence is less common but valuable for developing protease-resistant therapeutic peptides. No approved drugs contain this exact protected building block. It is commercially available for research use only.
|
| Molecular Formula |
C27H36N2O5
|
|---|---|
| Molecular Weight |
468.59
|
| Exact Mass |
468.262
|
| CAS # |
140834-91-9
|
| PubChem CID |
15138262
|
| Appearance |
White to off-white solid powder
|
| LogP |
5.178
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
5
|
| Rotatable Bond Count |
13
|
| Heavy Atom Count |
34
|
| Complexity |
646
|
| Defined Atom Stereocenter Count |
2
|
| SMILES |
CC(C)C[C@H](C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)OCC2=CC=CC=C2)NC(=O)OC(C)(C)C
|
| InChi Key |
IKZFNIAMQFYRSM-PKTZIBPZSA-N
|
| 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+/m1/s1
|
| Chemical Name |
benzyl (2S)-2-[[(2R)-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]amino]-3-phenylpropanoate
|
| 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 | 2.1341 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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
