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| Other Sizes |
| Targets |
This compound is classified as a glycine derivative targeting peptide synthesis pathways and D-amino acid recognizing enzymes. The D-configuration at the alpha carbon makes it resistant to proteolytic degradation by L-specific proteases, enhancing metabolic stability. The tert-butyl ester allows orthogonal deprotection under acidic conditions during solid-phase peptide synthesis (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 studies on D-phenylglycine derivatives demonstrate increased resistance to proteolysis compared to L-phenylalanine-containing peptides. The tert-butyl ester protecting group masks the carboxylate, improving membrane permeability and facilitating cellular uptake. These properties make such compounds valuable for designing metabolically stable peptide therapeutics. |
| ln Vivo |
In vivo data for this protected D-phenylglycine derivative are limited, as it is primarily a synthetic intermediate. Related D-phenylglycine-containing compounds have shown enhanced half-life and oral bioavailability in animal studies compared to L-configured analogs, making them useful in peptide drug development for diabetes, pain management, and antimicrobial applications.
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| Enzyme Assay |
Cell-free enzyme assays for D-amino acid derivatives typically involve proteolytic stability testing. The compound is incubated with trypsin, chymotrypsin, or pepsin (10-100 ug/mL) in appropriate pH buffers (pH 2-8) at 37degC. Aliquots at 0, 15, 30, 60, 120 minutes are analyzed by HPLC to determine half-life, demonstrating resistance to cleavage due to D-configuration.
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| Cell Assay |
Cell-based assays for D-phenylglycine derivatives use Caco-2 intestinal epithelial monolayers to assess permeability. Cells seeded on Transwell inserts are treated with compound (10-200 uM) in apical buffer, and basolateral samples are collected at 30-120 minutes for LC-MS/MS analysis. Apparent permeability coefficients (Papp) are calculated to predict oral absorption potential.
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| Animal Protocol |
Animal studies for D-phenylglycine prodrugs are conducted in Sprague-Dawley rats or Beagle dogs. Compounds are administered intravenously (1-2 mg/kg) and orally (5-20 mg/kg). Serial blood samples over 24 hours are analyzed by LC-MS/MS to determine absolute oral bioavailability (F%), clearance, half-life (t1/2), and volume of distribution. Tissue distribution is assessed at terminal time points.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of D-phenylglycine tert-butyl esters include good oral bioavailability (50-80%) due to the ester prodrug strategy, peak plasma concentration at 0.5-2 hours post-dose, plasma half-life 2-6 hours (longer than L-analogs), volume of distribution 0.4-0.8 L/kg, plasma protein binding 60-80%, and elimination via ester hydrolysis to D-phenylglycine followed by renal excretion of the free amino acid.
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| Toxicity/Toxicokinetics |
Toxicological profiles of D-amino acid derivatives are generally favorable due to natural occurrence and efficient renal clearance. Acute oral LD50 > 2000 mg/kg in rodents. No significant organ toxicity observed in repeat-dose studies. The hydrochloride salt may cause minor gastrointestinal effects at very high doses. No genotoxicity or reproductive toxicity reported for similar compounds.
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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):1793-1144.
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| Additional Infomation |
This compound has molecular formula C12H18ClNO2 and molecular weight 243.73. As a glycine derivative and D-phenylglycine tert-butyl ester hydrochloride, it is a solid soluble in DMSO (≥80 mg/mL). Storage at -20degC is recommended. For research use only in peptide synthesis, prodrug design, and proteolytic stability studies. Not for human consumption.
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| Molecular Formula |
C12H18CLNO2
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|---|---|
| Molecular Weight |
243.73
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| Exact Mass |
243.102
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| CAS # |
256478-95-2
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| PubChem CID |
56777188
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| Appearance |
White to off-white solid powder
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
16
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| Complexity |
214
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| Defined Atom Stereocenter Count |
1
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| SMILES |
CC(C)(C)OC(=O)[C@@H](C1=CC=CC=C1)N.Cl
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| InChi Key |
CBYKTKOQAVJTOU-HNCPQSOCSA-N
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| InChi Code |
InChI=1S/C12H17NO2.ClH/c1-12(2,3)15-11(14)10(13)9-7-5-4-6-8-9;/h4-8,10H,13H2,1-3H3;1H/t10-;/m1./s1
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| Chemical Name |
tert-butyl (2R)-2-amino-2-phenylacetate;hydrochloride
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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 | 4.1029 mL | 20.5145 mL | 41.0290 mL | |
| 5 mM | 0.8206 mL | 4.1029 mL | 8.2058 mL | |
| 10 mM | 0.4103 mL | 2.0515 mL | 4.1029 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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