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| Other Sizes |
| Targets |
Cleavable Linker
As a building block, Fmoc-Lys(Pal-Glu-OtBu)-OH does not have a traditional biological target. The compound is used in the synthesis of lipidated peptides that can target cell membranes or lipid rafts. The palmitoyl group provides lipophilicity, enabling membrane anchoring and improved cellular uptake. The glutamate moiety may contribute to the compound's interaction with cellular transporters or receptors. The compound serves as a structural component in peptide-based therapeutics. |
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| ln Vitro |
ADC cytotoxins are connected to antibodies through an ADC connector to form ADCs [1]. Two distinct ligands, one for the E3 ubiquitin ligase and the other for the target protein, are present in PROTAC and are joined by a linker. PROTAC selectively degrades target proteins by means of the intracellular ubiquitin-proteasome system [2].
In vitro, Fmoc-Lys(Pal-Glu-OtBu)-OH functions as a chemical building block rather than a bioactive compound. It is used in solid-phase peptide synthesis to introduce a lipidated lysine residue into peptide sequences. The Fmoc group allows for selective deprotection and coupling during synthesis. The palmitoyl-glutamate side chain provides lipophilicity, which can enhance the membrane permeability and cellular uptake of the resulting peptide. The compound itself does not exhibit direct cellular activity but enables the bioactivity of the conjugated peptide. |
| ln Vivo |
In vivo activity of Fmoc-Lys(Pal-Glu-OtBu)-OH is realized through the peptide or peptide-drug conjugate in which it is incorporated. The palmitoyl group can facilitate membrane anchoring and improve the pharmacokinetic properties of the peptide, including extended half-life and enhanced tissue distribution. The in vivo efficacy depends on the specific peptide sequence and therapeutic payload used in the conjugate.
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| Enzyme Assay |
In vitro enzyme/receptor binding assays for Fmoc-Lys(Pal-Glu-OtBu)-OH focus on evaluating the stability and reactivity of the building block. The compound is tested for its ability to be incorporated into peptide sequences during solid-phase synthesis. The purity and identity of the compound are verified by HPLC and mass spectrometry. The compound's stability under peptide synthesis conditions is assessed by monitoring for degradation or side reactions.
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| Cell Assay |
In vitro cellular assays for Fmoc-Lys(Pal-Glu-OtBu)-OH involve testing the complete peptide or peptide-drug conjugate rather than the building block alone. Cells are treated with the peptide, and effects on cell viability, proliferation, or specific cellular pathways are measured. The building block itself does not directly affect cell viability but is essential for the function of the conjugated peptide.
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| Animal Protocol |
In vivo animal studies for Fmoc-Lys(Pal-Glu-OtBu)-OH are conducted using the final peptide or peptide-drug conjugate. Animal models of disease are treated with the conjugate via various routes of administration. Pharmacokinetic parameters such as half-life, tissue distribution, and clearance are measured. Efficacy is assessed by measuring disease progression and relevant biomarkers. The building block contributes to the overall stability and PK profile of the conjugate.
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| ADME/Pharmacokinetics |
Fmoc-Lys(Pal-Glu-OtBu)-OH has a molecular formula of C₅₀H₇₅N₃O₁₀ and a molecular weight of 878.15. It appears as a white to off-white solid powder with a purity of ≥95%. It is soluble in DMSO and other organic solvents. The compound is stable under recommended storage conditions. It is intended for research use only and is not approved for clinical use.
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| Toxicity/Toxicokinetics |
The toxicity profile of Fmoc-Lys(Pal-Glu-OtBu)-OH is associated with the peptide or peptide-drug conjugate in which it is used. As a building block, it is considered to have low intrinsic toxicity. Standard toxicity studies for the final conjugate include assessment of body weight changes, clinical observations, hematological parameters, and histopathological examination of major organs in animal models. The building block itself does not exhibit significant cytotoxic effects in standard cell viability assays.
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| References |
[1]. Beck A, et al. Strategies and challenges for the next generation of antibody-drug conjugates. Nat Rev Drug Discov. 2017;16(5):315-337.
[2]. Nalawansha DA, et al. PROTACs: An Emerging Therapeutic Modality in Precision Medicine. Cell Chem Biol. 2020;27(8):998-985. |
| Additional Infomation |
Fmoc-Lys(Pal-Glu-OtBu)-OH (CAS 1491158-62-3) is a complex amino acid derivative used as a building block in peptide synthesis. It has a molecular formula of C₅₀H₇₅N₃O₁₀ and a molecular weight of 878.15. The compound features an Fmoc-protected lysine with a palmitoyl-glutamate side chain and a tert-butyl ester protection. It is used in the synthesis of lipidated peptides and peptide-drug conjugates. It is intended for research use only and is not approved for clinical use.
|
| Molecular Formula |
C46H69N3O8
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|---|---|
| Molecular Weight |
792.06
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| Exact Mass |
791.508
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| CAS # |
1491158-62-3
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| PubChem CID |
72188630
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| Appearance |
White to off-white solid powder
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
944.2±65.0 °C at 760 mmHg
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| Flash Point |
524.8±34.3 °C
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| Vapour Pressure |
0.0±0.3 mmHg at 25°C
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| Index of Refraction |
1.530
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| LogP |
11.05
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
31
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| Heavy Atom Count |
57
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| Complexity |
1180
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| Defined Atom Stereocenter Count |
2
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| SMILES |
O(C(N[C@H](C(=O)O)CCCCNC(CC[C@@H](C(=O)OC(C)(C)C)NC(CCCCCCCCCCCCCCC)=O)=O)=O)CC1C2C=CC=CC=2C2C=CC=CC1=2
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| InChi Key |
LQQXBYSAGYOQJW-ZAQUEYBZSA-N
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| InChi Code |
InChI=1S/C46H69N3O8/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-29-42(51)48-40(44(54)57-46(2,3)4)30-31-41(50)47-32-23-22-28-39(43(52)53)49-45(55)56-33-38-36-26-20-18-24-34(36)35-25-19-21-27-37(35)38/h18-21,24-27,38-40H,5-17,22-23,28-33H2,1-4H3,(H,47,50)(H,48,51)(H,49,55)(H,52,53)/t39-,40-/m0/s1
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| Chemical Name |
(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-[[(4S)-4-(hexadecanoylamino)-5-[(2-methylpropan-2-yl)oxy]-5-oxopentanoyl]amino]hexanoic 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 | 1.2625 mL | 6.3127 mL | 12.6253 mL | |
| 5 mM | 0.2525 mL | 1.2625 mL | 2.5251 mL | |
| 10 mM | 0.1263 mL | 0.6313 mL | 1.2625 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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