| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| Other Sizes |
| Targets |
The primary pharmacological target of Fmoc-Ala-Glu-Asn-Lys-NH2 is asparagine endopeptidase (AEP, also known as legumain), a cysteine protease that cleaves asparagine residues. The peptide selectively inhibits AEP and blocks the cleavage of amyloid precursor protein (APP), which is implicated in the pathogenesis of Alzheimer's disease. The Fmoc-protected tetrapeptide can also be used as a linker building block for antibody-drug conjugates (ADCs).
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| ln Vitro |
AEP's processing of APP is inhibited by Fmoc-Ala-Glu-Asn-Lys-NH2, whereas the inert peptide AEQK and other small molecule inhibitors had no impact [1].
In vitro, Fmoc-Ala-Glu-Asn-Lys-NH2 acts as a selective inhibitor of asparagine endopeptidase (AEP), preventing the proteolytic cleavage of amyloid precursor protein (APP). At inhibitory concentrations, the peptide reduces the generation of pathogenic amyloid-beta fragments by blocking AEP-mediated APP processing. The Fmoc protecting group provides orthogonal protection, enabling precise deprotection and coupling cycles during solid-phase peptide synthesis (SPPS). |
| ln Vivo |
In vivo activity data for Fmoc-Ala-Glu-Asn-Lys-NH2 is not provided in the available references, as its primary applications are in ex vivo peptide synthesis and as a biochemical tool for protease inhibition studies. For potential in vivo applications, the peptide would need to be conjugated to a delivery vehicle (e.g., as part of a PROTAC or ADC construct) to achieve cellular uptake and target engagement. The tetrapeptide itself is not intended for direct in vivo administration.
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| Enzyme Assay |
A non-cellular assay for AEP inhibition can be performed using purified recombinant human AEP. The enzyme is incubated with a fluorogenic substrate (e.g., Z-Ala-Ala-Asn-AMC, where AMC = 7-amino-4-methylcoumarin) and varying concentrations of Fmoc-Ala-Glu-Asn-Lys-NH2 in assay buffer (50 mM sodium citrate, pH 5.5, 5 mM DTT). After incubation at 37degC, the release of fluorescent AMC is measured (excitation 380 nm, emission 460 nm) to calculate the IC50 for inhibition.
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| Cell Assay |
For SPPS applications (not a cellular assay), the peptide is assembled stepwise on a solid resin support. Standard Fmoc-based SPPS protocols involve coupling each amino acid using HBTU/HOBt/DIPEA in DMF, followed by Fmoc deprotection with 20% piperidine in DMF. Fmoc-Ala-Glu-Asn-Lys-NH2 serves as a synthetic intermediate; after deprotection of the Fmoc group, the free amine can be used for further coupling of linkers or payloads for PROTAC or ADC synthesis.
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| Animal Protocol |
No specific in vivo animal protocol is described for Fmoc-Ala-Glu-Asn-Lys-NH2 in the provided references, as the compound is primarily used for ex vivo peptide synthesis and biochemical assays. If the peptide were incorporated into a PROTAC or ADC construct intended for in vivo use, the corresponding construct would be tested in a xenograft tumor model in immunocompromised mice. The peptide itself is a synthetic intermediate, not a final drug substance.
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| ADME/Pharmacokinetics |
No specific pharmacokinetic data is provided for Fmoc-Ala-Glu-Asn-Lys-NH2. As a tetrapeptide with a molecular weight of approximately 742.8 g/mol (Fmoc-protected) and significant hydrophilicity, it is expected to have very poor oral bioavailability, a short plasma half-life due to rapid proteolytic degradation, and limited cell membrane permeability unless conjugated to a cell-penetrating peptide or delivery vehicle.
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| Toxicity/Toxicokinetics |
No detailed toxicological data is available for Fmoc-Ala-Glu-Asn-Lys-NH2. As a peptide used as a synthetic intermediate, standard laboratory safety precautions should be followed. The trifluoroacetate (TFA) salt form is common for peptide handling, but TFA can be cytotoxic in vivo if not properly exchanged. The peptide should be treated as a potential irritant and handled with appropriate personal protective equipment (PPE).
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| References |
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| Additional Infomation |
Fmoc-Ala-Glu-Asn-Lys-NH2 is a valuable synthetic intermediate in peptide chemistry, particularly for the production of longer peptides and peptide-derived therapeutics. The Fmoc (9-fluorenylmethyloxycarbonyl) group is one of the most widely used protecting groups in solid-phase peptide synthesis (SPPS), as it is stable under acidic conditions and can be selectively removed under basic conditions (20% piperidine in DMF). This tetrapeptide sequence has applications in the synthesis of PROTACs, antibody-drug conjugates (ADCs), and peptide-based protease inhibitors for neurodegenerative disease research.
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| Molecular Formula |
C33H43N7O9
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|---|---|
| Molecular Weight |
681.74
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| Exact Mass |
681.312
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| CAS # |
220701-06-4
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| PubChem CID |
155971207
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| Appearance |
White to off-white solid powder
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| LogP |
-2.9
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| Hydrogen Bond Donor Count |
8
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| Hydrogen Bond Acceptor Count |
10
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| Rotatable Bond Count |
20
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| Heavy Atom Count |
49
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| Complexity |
1180
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| Defined Atom Stereocenter Count |
4
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| SMILES |
C1C=C2C3=CC=CC=C3C(COC(=O)N[C@H](C(=O)NC(C(N[C@@H](C(=O)N[C@@H](CCCCN)C(N)=O)CC(=O)N)=O)CCC(=O)O)C)C2=CC=1
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| InChi Key |
SAWVPDQXSCHRKB-UZTPZCRESA-N
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| InChi Code |
InChI=1S/C33H43N7O9/c1-18(37-33(48)49-17-23-21-10-4-2-8-19(21)20-9-3-5-11-22(20)23)30(45)39-25(13-14-28(42)43)31(46)40-26(16-27(35)41)32(47)38-24(29(36)44)12-6-7-15-34/h2-5,8-11,18,23-26H,6-7,12-17,34H2,1H3,(H2,35,41)(H2,36,44)(H,37,48)(H,38,47)(H,39,45)(H,40,46)(H,42,43)/t18-,24-,25-,26-/m0/s1
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| Chemical Name |
(4S)-5-[[(2S)-4-amino-1-[[(2S)-1,6-diamino-1-oxohexan-2-yl]amino]-1,4-dioxobutan-2-yl]amino]-4-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoyl]amino]-5-oxopentanoic 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: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| 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: 100 mg/mL (146.68 mM)
H2O: ≥ 10 mg/mL (14.67 mM) |
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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 | 1.4668 mL | 7.3342 mL | 14.6683 mL | |
| 5 mM | 0.2934 mL | 1.4668 mL | 2.9337 mL | |
| 10 mM | 0.1467 mL | 0.7334 mL | 1.4668 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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