| Size | Price | Stock | Qty |
|---|---|---|---|
| 100mg |
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| Other Sizes |
| Targets |
As a synthetic intermediate, Fmoc-1-methyl-L-histidine has no specific biological target. Its role is to provide 1-methylhistidine 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 1-methyl group on the imidazole ring introduces unique steric and electronic properties that can significantly alter peptide conformation and biological activity compared to unsubstituted histidine. 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 |
The in vitro activity of Fmoc-1-methyl-L-histidine 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 Fmoc-1-methyl-L-histidine (typically 3-5 equivalents) using coupling reagents such as HATU, HBTU, or DIC with HOBt, and DIEA as base. Coupling efficiency is monitored by the Kaiser test or by quantitative HPLC. Purity is assessed by HPLC (≥98.0%). No inherent biological activity is observed as the compound is a protected amino acid derivative.
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| ln Vivo |
In vivo activity is not applicable for Fmoc-1-methyl-L-histidine. The compound is not used in animals and is a research chemical for laboratory synthesis only.
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| Enzyme Assay |
The in vitro enzyme/receptor binding (non-cellular) experimental workflow for Fmoc-1-methyl-L-histidine 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 Fmoc-1-methyl-L-histidine (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 compound's SMILES is [n]1(cnc(c1)C[C@H](NC(=O)OCC2c3c(cccc3)c4c2cccc4)C(=O)O)C.
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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.
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| Animal Protocol |
In vivo animal experiments are not applicable for Fmoc-1-methyl-L-histidine. The compound is stored at 2-8°C.
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| ADME/Pharmacokinetics |
The pharmacokinetic properties have not been characterized. The compound is not a drug. The compound is stable under recommended storage conditions.
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| Toxicity/Toxicokinetics |
The toxicological data are limited. Standard laboratory safety practices should be followed.
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| References | |
| Additional Infomation |
See other relationships...
Fmoc-1-methyl-L-histidine is an Fmoc-protected, N-τ-methylated L-histidine derivative used as a building block for Fmoc SPPS. The 1-methyl group on the imidazole ring introduces unique steric and electronic properties. The compound is not a drug and has no clinical trials or approvals. The compound is for research use only. Novabiochem is a registered trademark. |
| Molecular Formula |
C22H21N3O4
|
|---|---|
| Molecular Weight |
391.42
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| Exact Mass |
391.153
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| CAS # |
202920-22-7
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| PubChem CID |
7010694
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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
|
| SMILES |
CN1C=C(N=C1)C[C@H](NC(OCC2C3=CC=CC=C3C4=CC=CC=C42)=O)C(O)=O
|
| InChi Key |
SLWOFHRSEVVUHM-FQEVSTJZSA-N
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| InChi Code |
InChI=1S/C22H21N3O4/c1-25-11-14(23-13-25)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
|
| Chemical Name |
(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(1-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) |
DMSO: 125 mg/mL (319.35 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (5.31 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (5.31 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.08 mg/mL (5.31 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| 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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