![D-Phenylalanine, N-[N-[(1,1-dimethylethoxy)carbonyl]-D-leucyl]-, phenylmethyl ester](/upload/1124/V68201.png)
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| 50mg |
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| 100mg |
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| Other Sizes |
| Targets |
This compound is classified as a phenylalanine derivative and D-dipeptide analog targeting proteases that recognize D-amino acid configurations. The D-configuration at both residues confers resistance to L-specific proteases, making it useful for studying peptide stability in biological systems. The Boc group allows acid-labile deprotection, while the benzyl ester is removable by hydrogenation.
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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 studies on D-dipeptides demonstrate dramatically increased metabolic stability compared to L-configured analogs, with half-lives extending from minutes to hours in plasma and tissue homogenates. D-Phenylalanine-containing peptides are also resistant to bacterial and mammalian proteases, making them valuable for developing orally active peptide therapeutics. |
| ln Vivo |
In vivo studies on D-dipeptides in rodent models show prolonged circulation time (5-10 fold longer than L-analogs), reduced immunogenicity, and preserved biological activity. These properties make D-dipeptide scaffolds attractive for developing stable peptide drugs for pain management, metabolic disorders, and infectious diseases requiring sustained target engagement.
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| Enzyme Assay |
Cell-free protease assays for D-dipeptides use purified enzymes (trypsin, chymotrypsin, elastase, pepsin). Compound (10-500 uM) is incubated with enzyme (0.1-10 ug/mL) in pH-optimized buffer at 37degC. Aliquots are taken at 0-240 minutes and analyzed by HPLC-MS to determine degradation half-life, comparing D- vs L-configured analogs. Resistance confirms stability in specific biological compartments.
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| Cell Assay |
Cell-based assays for D-dipeptides use Caco-2 monolayers for permeability assessment. Cells are grown on Transwell inserts for 21 days, treated with compound (10-200 uM) in the apical chamber, and basolateral samples are analyzed by LC-MS/MS at 0-120 minutes. Apparent permeability coefficients (Papp) are calculated for oral absorption prediction, typically higher than peptides due to protease resistance.
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| Animal Protocol |
Animal studies for D-dipeptide analogs are conducted in male CD-1 mice or Sprague-Dawley rats. Animals receive intravenous (1-5 mg/kg) and oral (10-50 mg/kg) administration. Blood collected at 0, 0.25, 0.5, 1, 2, 4, 8, 12, 24 hours is analyzed by LC-MS/MS. Pharmacokinetic parameters (Cmax, Tmax, AUC, t1/2, F%) are calculated using non-compartmental analysis in validated software.
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| Toxicity/Toxicokinetics |
Toxicological profiles of D-dipeptides are generally favorable due to efficient renal excretion of D-amino acids. Acute oral LD50 > 2000 mg/kg in rodents. No significant hepatotoxicity, nephrotoxicity, or neurotoxicity in repeat-dose studies at therapeutic doses. D-Amino acids are not immunogenic and are cleared rapidly. No genotoxicity observed in standard Ames and micronucleus assays.
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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):1793-1016.
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| Additional Infomation |
This compound has molecular formula C27H36N2O5 and molecular weight 468.59. It appears as a solid soluble in DMSO (≥80 mg/mL) and is used in peptide synthesis and drug development research. Storage at -20degC for powder or -80degC for solutions is recommended. This phenylalanine derivative is for research use only, not for human consumption.
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| Molecular Formula |
C27H36N2O5
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| Molecular Weight |
468.59
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| Exact Mass |
468.262
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| CAS # |
159549-97-0
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| PubChem CID |
40592906
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| Appearance |
White to light yellow 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-DHIUTWEWSA-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-/m1/s1
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| Chemical Name |
benzyl (2R)-2-[[(2R)-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) |
DMSO: ≥ 100 mg/mL (213.41 mM)
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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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