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| Other Sizes |
| Targets |
Boc-D-Phg-OH targets peptide synthesis applications as a building block for introducing D-phenylglycine residues. The phenyl group offers structural rigidity, influencing the conformational properties and biological activity of the resulting peptides. As a D-amino acid derivative, it imparts different stereochemical properties compared to its L-counterpart. It is used in the synthesis of peptides and peptidomimetics for drug discovery programs targeting various enzymes and receptors.
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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 Boc-D-Phg-OH is primarily as a peptide synthesis building block. The D-phenylglycine residue introduced via this compound can confer enhanced conformational stability and resistance to enzymatic degradation to the resulting peptides. Peptides containing D-phenylglycine have been studied for various biological activities including antimicrobial and enzyme inhibitory properties. The compound itself is not biologically active in cell-based assays. |
| ln Vivo |
There is no specific in vivo activity data for Boc-D-Phg-OH as it is a protected amino acid building block. Peptides and peptidomimetics synthesized using this compound may be evaluated in animal models for therapeutic efficacy. The D-configuration and phenyl group can improve metabolic stability and target binding affinity of the resulting peptide drugs. Boc-D-Phg-OH is used in the synthesis of enzyme inhibitors and other bioactive compounds.
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| Enzyme Assay |
In vitro enzyme/receptor binding protocols for Boc-D-Phg-OH involve its use in peptide synthesis rather than direct binding assays. Standard SPPS protocols: the compound is activated using coupling reagents such as HATU, HBTU, or DIC in DMF with a base. The activated ester is coupled to a resin-bound peptide chain. Deprotection of the Boc group is achieved with TFA. Coupling efficiency is monitored by HPLC or Kaiser test. Purity specifications require ≥98% by HPLC and ≥98% enantiomeric purity.
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| Cell Assay |
Cell-based protocols are not directly applicable to Boc-D-Phg-OH as it is a synthetic building block. However, peptides synthesized using this compound can be tested in cellular assays. Peptides are dissolved in suitable solvents, filtered, and added to cell cultures at concentrations of 0.1-100 µM. Cells are incubated for 24-72 hours, and effects on cell viability, proliferation, or signaling are measured using standard assays such as MTT, BrdU incorporation, or Western blotting.
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| Animal Protocol |
Animal studies with Boc-D-Phg-OH are not conducted directly. Peptides containing D-phenylglycine residues synthesized using this building block may be evaluated in vivo. Standard protocols involve administration of the peptide via appropriate routes (IV, IP, PO) in animal models. Dosing, blood sampling, and tissue collection follow standard PK/PD study designs. Efficacy endpoints depend on the therapeutic target. The D-phenylglycine residue can improve peptide stability and bioavailability.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for Boc-D-Phg-OH is not applicable as it is a research building block. The compound has a molecular weight of 251.28 g/mol and formula C₁₃H₁₇NO₄. It appears as a white to almost white powder with a melting point ≥98% purity and ≥98% enantiomeric purity. It is soluble in organic solvents for peptide synthesis. The Boc protecting group is removed under acidic conditions during peptide synthesis.
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| Toxicity/Toxicokinetics |
Toxicological data for Boc-D-Phg-OH is limited. Standard safety precautions for handling Boc-protected amino acids should be observed. The compound is not intended for human therapeutic use. Acute toxicity is expected to be low based on its chemical class. Store at room temperature or as recommended by the manufacturer. Proper personal protective equipment should be worn when handling. The compound is for research use only.
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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 |
Boc-D-Phg-OH (CAS#: 33125-05-2) is also known as N-Boc-D-phenylglycine, (2R)-2-{[(tert-butoxy)carbonyl]amino}-2-phenylacetic acid. Its molecular formula is C₁₃H₁₇NO₄ and molecular weight is 251.28 g/mol. It is a critical building block in Boc-based solid-phase peptide synthesis. The D-configuration and phenyl group provide structural rigidity and influence peptide conformation. It is used in the synthesis of peptidomimetics and enzyme inhibitors. It has no approved therapeutic indications.
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| Molecular Formula |
C13H17NO4
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|---|---|
| Molecular Weight |
251.27838
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| Exact Mass |
251.115
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| CAS # |
33125-05-2
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| PubChem CID |
2755953
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| Appearance |
White to off-white powder
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| Density |
1.2±0.1 g/cm3
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| Boiling Point |
382.6±25.0 °C at 760 mmHg
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| Melting Point |
88-91 °C
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| Flash Point |
185.2±23.2 °C
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| Vapour Pressure |
0.0±0.9 mmHg at 25°C
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| Index of Refraction |
1.557
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| LogP |
2.95
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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 |
5
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| Heavy Atom Count |
18
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| Complexity |
303
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| Defined Atom Stereocenter Count |
1
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| SMILES |
O=C(O)[C@H](NC(OC(C)(C)C)=O)C1=CC=CC=C1
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| InChi Key |
HOBFSNNENNQQIU-SNVBAGLBSA-N
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| InChi Code |
InChI=1S/C13H17NO4/c1-13(2,3)18-12(17)14-10(11(15)16)9-7-5-4-6-8-9/h4-8,10H,1-3H3,(H,14,17)(H,15,16)/t10-/m1/s1
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| Chemical Name |
(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylacetic acid
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| Synonyms |
(2R)-2-(tert-Butoxycarbonylamino)-2-phenylethanoic acid; (αR)-α-[[(1,1-Dimethylethoxy)carbonyl]amino]benzeneacetic acid; (R)-2-((tert-Butoxycarbonyl)amino)-2-phenylacetic acid; (R)-2-[(tert-Butoxycarbonyl)amino]-2-phenylacetic acid
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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 | 3.9796 mL | 19.8981 mL | 39.7962 mL | |
| 5 mM | 0.7959 mL | 3.9796 mL | 7.9592 mL | |
| 10 mM | 0.3980 mL | 1.9898 mL | 3.9796 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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