![N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-O-(phenylmethyl)-D-serine](/upload/1124/V68090.png)
| Size | Price | Stock | Qty |
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| 25g |
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| Other Sizes |
| Targets |
As a synthetic intermediate, N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-O-(phenylmethyl)-D-serine has no specific biological target. Its role is to provide O-benzyl-D-serine residues in peptide chains. The Fmoc protecting group enables standard Fmoc solid-phase peptide synthesis (SPPS) workflows, allowing for the controlled assembly of peptide chains. The benzyl ether protecting group on the hydroxyl side chain prevents unwanted side reactions during peptide synthesis and can be selectively removed to generate free serine residues or to introduce modifications at the hydroxyl position. The D-configuration of the serine residue introduces stereochemical diversity compared to L-serine, which can be valuable for structure-activity relationship studies. The compound does not interact with enzymes or receptors in pharmacological assays. Its "target" is the peptide coupling reaction, where it acts as a protected amino acid donor.
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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].
The in vitro activity of N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-O-(phenylmethyl)-D-serine is measured by coupling efficiency in solid-phase peptide synthesis (SPPS). Typically, it is coupled to resin-bound amine using standard Fmoc-SPPS conditions: deprotection of the resin-bound Fmoc group with 20% piperidine in DMF, followed by coupling with the compound (typically 3-5 equivalents) using coupling reagents such as HATU, HBTU, or DIC with HOBt, and DIEA as base. The coupling reaction is typically performed at room temperature for 1-4 hours. Coupling efficiency is monitored by the Kaiser test (ninhydrin test) or by quantitative HPLC. Cleavage and deprotection with TFA/TIS/H₂O yield the desired peptide. Purity is ≥98%. No inherent biological activity is observed as the compound is a protected amino acid derivative. Amino acids and amino acid derivatives have been commercially used as ergogenic supplements. |
| ln Vivo |
In vivo activity is not applicable for N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-O-(phenylmethyl)-D-serine. The compound is not used in animals and is a research chemical for laboratory synthesis only. It is not intended for therapeutic or diagnostic purposes.
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| Enzyme Assay |
The in vitro enzyme/receptor binding (non-cellular) experimental workflow for N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-O-(phenylmethyl)-D-serine involves standard Fmoc solid-phase peptide synthesis procedures. Standard SPPS cycle: deprotect Fmoc with 20% piperidine in DMF (typically 2 × 5-10 minutes), wash with DMF, couple the compound (3 equiv.) with HATU (2.9 equiv.) and DIEA (6 equiv.) for 1-2 hours, wash, repeat. After complete assembly of the peptide sequence, the peptide is cleaved from the resin and deprotected using a cleavage cocktail containing TFA, TIS, and water (typically 95:2.5:2.5) for 2-4 hours. The crude peptide is precipitated with cold ether, and the product is analyzed by HPLC-MS. The compound's LogP is 6, indicating high lipophilicity. The compound has a boiling point of 642.4±55.0 °C and a density of 1.3±0.1 g/cm³.
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| Cell Assay |
In vitro cell-based experimental workflows are not performed on this intermediate. The final deprotected peptides may be tested in cell-based assays, but the protected compound itself is not used. When the final deprotected peptide is tested, typical assays might include cell viability (MTT assay), apoptosis detection (Annexin V staining), or receptor binding studies depending on the biological target of the synthesized peptide. Cells are typically cultured in DMEM with 10% FBS, treated with peptide concentrations ranging from 0.1 to 100 µM for 24-72 hours, and read by plate reader or flow cytometry.
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| Animal Protocol |
In vivo animal experiments are not applicable for N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-O-(phenylmethyl)-D-serine. The compound is stored as a powder at -20°C or 4°C. The compound is not formulated for any route of administration. Any in vivo studies would involve the final deprotected peptide products rather than the protected amino acid itself.
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| ADME/Pharmacokinetics |
The pharmacokinetic properties of N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-O-(phenylmethyl)-D-serine have not been characterized. The compound is not a drug. No ADME data are available. The compound is stable under recommended storage conditions: powder at -20°C for up to 3 years or at 4°C for up to 2 years; in solvent at -80°C for up to 1 month. If administered, the Fmoc and benzyl protecting groups would likely be cleaved metabolically, releasing the free amino acid, but such studies are not conducted with this protected amino acid.
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| Toxicity/Toxicokinetics |
The toxicological data for N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-O-(phenylmethyl)-D-serine are not well-documented. Standard laboratory safety practices should be followed. The compound is intended for research use only and is not approved for human or veterinary applications. No chronic toxicity, carcinogenicity, or reproductive toxicity studies have been conducted, as these are not relevant for a synthetic intermediate.
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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 |
N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-O-(phenylmethyl)-D-serine is a serine analogue and a valuable building block for Fmoc-based solid-phase peptide synthesis. The compound is a serine derivative and is commercially available with purity ≥98%. The benzyl ether modification introduces increased lipophilicity and steric bulk compared to unprotected serine. The compound is not a drug and has no clinical trials or approvals. The compound is for research use only. The Fmoc protecting group enables standard SPPS workflows, making this compound widely used in peptide research.
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| Molecular Formula |
C25H23NO5
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| Molecular Weight |
417.45
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| Exact Mass |
417.157
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| CAS # |
122889-11-6
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| PubChem CID |
7019719
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| Appearance |
White to off-white solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
642.4±55.0 °C at 760 mmHg
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| Flash Point |
342.3±31.5 °C
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| Vapour Pressure |
0.0±2.0 mmHg at 25°C
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| Index of Refraction |
1.621
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| LogP |
6
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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 |
9
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| Heavy Atom Count |
31
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| Complexity |
583
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| Defined Atom Stereocenter Count |
1
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| SMILES |
C1=CC=C(C=C1)COC[C@H](C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
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| InChi Key |
DYBDGLCDMLNEMJ-HSZRJFAPSA-N
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| InChi Code |
InChI=1S/C25H23NO5/c27-24(28)23(16-30-14-17-8-2-1-3-9-17)26-25(29)31-15-22-20-12-6-4-10-18(20)19-11-5-7-13-21(19)22/h1-13,22-23H,14-16H2,(H,26,29)(H,27,28)/t23-/m1/s1
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| Chemical Name |
(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenylmethoxypropanoic 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 | 2.3955 mL | 11.9775 mL | 23.9550 mL | |
| 5 mM | 0.4791 mL | 2.3955 mL | 4.7910 mL | |
| 10 mM | 0.2395 mL | 1.1977 mL | 2.3955 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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