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| Targets |
Fmoc-D-histidine does not possess a specific biological target; its primary function is as a chemical building block for peptide synthesis. As a D-histidine derivative, it is used to introduce D-histidine residues into peptide chains, which can enhance peptide stability against enzymatic degradation and modulate biological activity. The Fmoc group serves as a temporary protecting group for the amino functionality, allowing for selective deprotection under basic conditions (typically piperidine in DMF) during Fmoc SPPS workflows. This enables chemists to build complex peptides with specific sequences while preventing unwanted reactions. The imidazole side chain can participate in metal coordination and proton transfer reactions, making histidine-containing peptides important for studying enzyme mechanisms and protein function.
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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].
This compound is not a biological agent and does not exhibit direct in vitro biological activity in a pharmacological sense. Its value lies exclusively in its chemical utility as a protected amino acid building block for constructing D-histidine-containing peptides and proteins. Amino acid derivatives like this one have been commercially used as ergogenic supplements affecting anabolic hormone release, fuel availability, and the prevention of muscular damage from exertion, but Fmoc-D-histidine itself is not tested for such activities. Any biological activity would reside in the final deprotected peptide product synthesized using this building block, not in the protected intermediate itself. |
| ln Vivo |
Fmoc-D-histidine is not administered in vivo as a therapeutic agent. It is a research chemical utilized exclusively as a building block in peptide synthesis. The final deprotected peptide product, not this protected intermediate, would be the subject of in vivo pharmacological testing for therapeutic efficacy and safety. If a D-histidine-containing peptide shows promising biological activity in vitro, it could be advanced to animal studies, but the protected amino acid building block itself is never administered to animals as a test compound. The compound is for research use only and is not intended for human or veterinary therapeutic applications.
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| Enzyme Assay |
Non-cellular enzyme/receptor binding assays are not applicable to Fmoc-D-histidine as it is not biologically active. Its use is exclusively in organic synthesis and peptide chemistry. A typical protocol involves its use as a building block in Fmoc SPPS, where the Fmoc group is removed with a base (e.g., 20% piperidine in DMF) to reveal the free amino group for coupling with the next amino acid using standard coupling reagents such as HATU, HBTU, or DIC/HOBt. The progress of coupling and deprotection can be monitored by standard analytical techniques such as TLC or HPLC. The C-terminal amino acid group is detectable by TLC or HPLC depending on the solvent system used.
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| Cell Assay |
Fmoc-D-histidine is not used in cell-based assays as a therapeutic agent. Its applications are in synthetic chemistry and peptide synthesis. It is typically stored as a powder at -20°C or below, and it is recommended to use it within one month after dissolving in solvent due to potential stability issues in solution. The compound is a white to off-white solid powder. It is soluble in common organic solvents such as DMF and DMSO, which are standard solvents for SPPS. Purity is typically ≥95% by HPLC. The product is for research purposes only and is not intended for diagnostic or therapeutic use.
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| Animal Protocol |
In vivo animal experiments do not involve Fmoc-D-histidine as a test article. It is a chemical intermediate used exclusively in the synthesis of peptide-based drug candidates. If a researcher synthesizes a therapeutic peptide containing D-histidine using this building block, that final deprotected and purified peptide product would be subjected to animal testing for pharmacokinetics, efficacy, and toxicity. The Fmoc-protected amino acid itself is never administered to animals as a test compound, as the protecting groups would interfere with any potential biological activity and could be toxic.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties are not applicable to Fmoc-D-histidine as it is not a drug. It is a small molecule (MW 377.39 g/mol) with the formula C21H19N3O4. Its physical properties include a predicted density of 1.372±0.06 g/cm3. These properties are relevant for chemical handling and storage rather than for systemic exposure or absorption, distribution, metabolism, and excretion (ADME) studies. The compound is not designed to be bioavailable, as the Fmoc and other protecting groups are intended to be removed during peptide synthesis to yield the final active peptide product.
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| Toxicity/Toxicokinetics |
The toxicity of Fmoc-D-histidine is not extensively documented, as it is a research chemical not intended for human or veterinary use. As with all Fmoc-protected amino acids, standard laboratory safety precautions should be followed, including handling in a well-ventilated area with appropriate personal protective equipment (gloves, lab coat, safety glasses). The compound should be stored as a powder at -20°C or below and protected from moisture. It is not intended for diagnostic, therapeutic, or other medical applications. In case of accidental exposure, standard first-aid measures for chemical irritants should be applied.
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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 |
Fmoc-D-histidine (Nα-Fmoc-D-histidine) is a specialized building block for peptide synthesis that enables the incorporation of D-histidine into peptides and proteins. D-amino acids are increasingly used in peptide drug development to enhance proteolytic stability and modulate biological activity. Histidine is a particularly important amino acid due to its imidazole side chain, which can participate in metal coordination, proton transfer, and catalytic mechanisms in enzymes. The Fmoc protecting group is the most widely used Nα-protecting group in modern SPPS due to its stability under acidic conditions and ease of removal under mild basic conditions. This compound is not a pharmaceutical and has no clinical trials or approved therapeutic status.
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| Molecular Formula |
C21H19N3O4
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| Molecular Weight |
377.39
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| Exact Mass |
377.137
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| CAS # |
157355-79-8
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| PubChem CID |
7019712
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| Appearance |
White to off-white solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
706.7±60.0 °C at 760 mmHg
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| Flash Point |
381.2±32.9 °C
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| Vapour Pressure |
0.0±2.4 mmHg at 25°C
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| Index of Refraction |
1.655
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| LogP |
3.03
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
28
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| Complexity |
550
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| Defined Atom Stereocenter Count |
1
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| SMILES |
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@H](CC4=CN=CN4)C(=O)O
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| InChi Key |
SIRPVCUJLVXZPW-LJQANCHMSA-N
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| InChi Code |
InChI=1S/C21H19N3O4/c25-20(26)19(9-13-10-22-12-23-13)24-21(27)28-11-18-16-7-3-1-5-14(16)15-6-2-4-8-17(15)18/h1-8,10,12,18-19H,9,11H2,(H,22,23)(H,24,27)(H,25,26)/t19-/m1/s1
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| Chemical Name |
(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(1H-imidazol-5-yl)propanoic 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 Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| 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 | 2.6498 mL | 13.2489 mL | 26.4978 mL | |
| 5 mM | 0.5300 mL | 2.6498 mL | 5.2996 mL | |
| 10 mM | 0.2650 mL | 1.3249 mL | 2.6498 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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