| Size | Price | Stock | Qty |
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| 100mg |
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| 250mg |
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| 500mg |
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| Other Sizes |
| Targets |
Fmoc-His(3-Me)-OH is not a drug and does not have a direct biological target; it is a synthetic building block used in Fmoc solid-phase peptide synthesis (SPPS). The compound is designed to introduce a 3-methylhistidine residue (a post-translational modification found in certain proteins, such as myosin) into synthetic peptides. The methyl group at the N3 position of the imidazole ring alters the tautomeric equilibrium and metal-coordinating properties of the histidine side chain, which is crucial for studying enzyme mechanisms and protein-protein interactions involving histidine residues.
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| ln Vitro |
As a chemical synthetic intermediate, Fmoc-His(3-Me)-OH does not have inherent in vitro biological activity. Its purpose is as a building block for peptide synthesis. Any biological activity would be associated with the final deprotected peptide or compound synthesized using this derivative. However, it has been reported that the tripeptide formed with Fmoc-His(3-Me)-OH, together with Fmoc-citrulline-OH and Fmoc-His(1-Me)-OH, exhibits vasodilating effects in phenylephrine-contracted aorta rings, with EC50 values of 2.7-4.7 mM, indicating that the final deprotected peptide can be bioactive. This compound is used to generate methyl-His-Gly-Lys peptides that act as [Ca2+]i inhibitors.
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| ln Vivo |
Fmoc-His(3-Me)-OH is not an active pharmaceutical ingredient and does not have in vivo biological activity on its own. It is exclusively a reagent for the chemical synthesis of peptides and peptidomimetics. Any in vivo effects would only be observed after the intermediate has been incorporated into a larger, biologically active molecule (e.g., a methylated histidine-containing peptide) and that molecule has been administered to an animal. For example, the methylated histidine-containing peptide generated from this building block could potentially inhibit intracellular calcium levels or induce vasodilation.
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| Enzyme Assay |
For non-cell-based assays, this compound is used as a reactant in peptide synthesis. A standard protocol involves dissolving Fmoc-His(3-Me)-OH in DMF or DCM. The Fmoc group is removed by treatment with 20% piperidine in DMF for 20 minutes. The identity and purity of the compound are confirmed by HPLC (typically ≥98% purity) and mass spectrometry. For peptide coupling, the free carboxylic acid is activated with HBTU/HOBt or HATU in the presence of DIPEA (diisopropylethylamine) and then reacted with a resin-bound or solution-phase amine. The incorporation of the 3-methylhistidine residue into the peptide sequence is confirmed by HPLC-MS after cleavage from the resin.
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| Cell Assay |
This chemical intermediate is not used directly in cell-based assays. It is designed as a building block for peptide synthesis. A typical workflow involves coupling Fmoc-His(3-Me)-OH to a growing peptide chain on a solid support (e.g., Rink amide resin or Wang resin) using standard Fmoc SPPS protocols. After the full peptide sequence is assembled and deprotected, the peptide is cleaved from the resin, purified by preparative HPLC (C18 column, water/acetonitrile gradient with 0.1% TFA), and then tested on cells in a functional assay such as calcium flux measurement, receptor binding, or enzyme inhibition. For example, a methyl-His-Gly-Lys-containing peptide could be tested for its ability to inhibit intracellular calcium concentration ([Ca2+]i).
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| Animal Protocol |
Fmoc-His(3-Me)-OH is not used directly in animal experiments, as it is a synthetic intermediate. It serves as a building block for the synthesis of peptides that are then administered to animals. For pharmacokinetic or biodistribution studies of a final peptide drug containing the 3-methylhistidine residue, the radiolabeled version of the drug would be synthesized. This could be achieved by starting with a 13C/15N-labeled version of this building block. The final labeled peptide would then be administered to rodents, and samples would be analyzed by LC-MS/MS to determine its PK profile. The building block itself is never administered.
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| ADME/Pharmacokinetics |
Fmoc-His(3-Me)-OH has a molecular weight of 391.43 g/mol and a molecular formula of C22H21N3O4. The Fmoc group is base-labile, while the methyl group on the imidazole is stable under both acidic and basic conditions. The compound is soluble in organic solvents such as DMF, DCM, and DMSO but is insoluble in water. Pharmacokinetic studies are not performed on this synthetic intermediate because it is not intended for systemic administration. The Fmoc protecting group is designed to be removed during peptide synthesis, and the final peptide's PK properties will be determined by the overall peptide sequence and structure.
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| Toxicity/Toxicokinetics |
Formal toxicology data is not available for this compound as it is a chemical reagent, not a clinical drug. It is intended for research use only and not for human use. Standard safety data sheets classify it as a potential irritant. It should be handled with care using appropriate personal protective equipment (lab coat, gloves, safety glasses) in a well-ventilated area. Avoid dust formation and inhalation. No specific acute or chronic toxicity data has been determined. It is not a known carcinogen or reproductive hazard.
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| References |
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| Additional Infomation |
Fmoc-His(3-Me)-OH is a specialized building block for Fmoc solid-phase peptide synthesis (SPPS) of methylated histidine-containing peptides. The methylation of histidine at the N3 position (τ-methylhistidine) is a naturally occurring post-translational modification found in proteins such as myosin, where it plays a role in modulating protein function. This compound allows researchers to incorporate this non-natural amino acid into synthetic peptides for structure-function studies, particularly in the fields of enzymology, metalloprotein chemistry, and muscle physiology. The 3-methylhistidine residue also serves as an internal standard for measuring muscle protein breakdown by LC-MS analysis of hydrolyzed protein samples. This product is not a drug and has no clinical approval status.
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| Molecular Formula |
C22H21N3O4
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| Molecular Weight |
391.42000
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| Exact Mass |
391.153
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| CAS # |
252049-16-4
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| PubChem CID |
7010692
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| Appearance |
White to off-white solid powder
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| LogP |
3.345
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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 |
7
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| Heavy Atom Count |
29
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| Complexity |
579
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| Defined Atom Stereocenter Count |
1
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| SMILES |
CN1C=NC=C1C[C@@H](C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
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| InChi Key |
UEDYXEZHNPXCFB-FQEVSTJZSA-N
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| InChi Code |
InChI=1S/C22H21N3O4/c1-25-13-23-11-14(25)10-20(21(26)27)24-22(28)29-12-19-17-8-4-2-6-15(17)16-7-3-5-9-18(16)19/h2-9,11,13,19-20H,10,12H2,1H3,(H,24,28)(H,26,27)/t20-/m0/s1
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| Chemical Name |
(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(3-methylimidazol-4-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 |
| 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 | 2.5548 mL | 12.7740 mL | 25.5480 mL | |
| 5 mM | 0.5110 mL | 2.5548 mL | 5.1096 mL | |
| 10 mM | 0.2555 mL | 1.2774 mL | 2.5548 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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