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| Other Sizes |
| Targets |
As an arginine analogue and protected amino acid derivative, Fmoc-HoArg(Pbf)-OH does not have a defined primary biological target as a standalone compound. Its primary role is as a building block for introducing homoarginine into peptides during SPPS. When incorporated into peptides, homoarginine provides an extended basic side chain that can enhance charge interactions and mimic arginine functionalities in biological systems. Researchers leverage this compound to explore protein engineering, structure-activity relationships, and the role of basic residues in biological systems.
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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].
As an arginine analogue and amino acid derivative, Fmoc-HoArg(Pbf)-OH has been studied in the context of amino acid and amino acid derivative research. Amino acids and their derivatives have been commercially used as ergogenic supplements, affecting the release of anabolic hormones, the availability of fuel for activity, mental performance under stress, and the prevention of exercise-induced muscle damage. They are regarded as advantageous synergistic food ingredients. When incorporated into peptides, homoarginine provides an extended basic side chain that can enhance charge interactions and influence biological activity. |
| ln Vivo |
Specific in vivo activity data for Fmoc-HoArg(Pbf)-OH as a standalone compound are not documented in the literature. As a protected amino acid building block for peptide synthesis, its in vivo effects are determined by the final peptide construct into which it is incorporated. Homoarginine-containing peptides can exhibit enhanced charge interactions and altered biological activities compared to arginine-containing analogs. The extended side chain of homoarginine may influence receptor binding, enzyme inhibition, or cellular uptake of the final peptide. The Pbf and Fmoc protecting groups are typically removed during peptide synthesis before in vivo applications.
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| Enzyme Assay |
In vitro enzyme/receptor binding assays for Fmoc-HoArg(Pbf)-OH typically involve its use as a building block in peptide synthesis rather than direct binding evaluation. When incorporated into peptides, the resulting homoarginine-containing constructs can be assessed for target binding affinity using standard biochemical assays such as radioligand binding, fluorescence polarization, or surface plasmon resonance (SPR). The extended basic side chain of homoarginine can enhance electrostatic interactions with negatively charged binding pockets. Typical assay conditions include buffered solutions at physiological pH.
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| Cell Assay |
In vitro cell-based studies using Fmoc-HoArg(Pbf)-OH typically focus on the biological activities of peptides synthesized with this building block rather than the compound itself. When incorporated into peptides, the resulting homoarginine-containing constructs can be evaluated in various cell-based assays including cell viability assays, receptor binding and internalization studies, and functional readouts such as calcium flux, nitric oxide production, or signaling pathway activation. Homoarginine can modulate peptide interactions with cell surface receptors and influence cellular uptake. Standard cell culture conditions (37°C, 5% CO₂) with appropriate cell lines are employed.
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| Animal Protocol |
In vivo animal studies using Fmoc-HoArg(Pbf)-OH are conducted with peptides synthesized from this building block rather than the compound itself. Typical experimental designs involve administration of the homoarginine-containing peptide construct to rodent models (e.g., mice or rats) via appropriate routes. Homoarginine can enhance peptide stability and modulate pharmacokinetic properties by influencing charge interactions and receptor binding. Endpoints may include efficacy measurements (e.g., tumor growth inhibition, biomarker modulation, cardiovascular parameters), pharmacokinetic sampling, and toxicological assessments. All procedures must comply with institutional animal care and use guidelines.
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| ADME/Pharmacokinetics |
Specific pharmacokinetic data for Fmoc-HoArg(Pbf)-OH as a standalone compound are not well characterized. The compound is soluble in DMSO at 125 mg/mL (188.59 mM). It is typically stored as a powder at -20°C (stable for 3 years) or 4°C (stable for 2 years); in solvent, it can be stored at -80°C for 6 months or -20°C for 1 month. When incorporated into peptides, the pharmacokinetic properties are determined by the overall peptide construct. Homoarginine incorporation can influence peptide stability, charge distribution, and receptor-mediated clearance. The Pbf and Fmoc protecting groups are removed during peptide synthesis before in vivo applications.
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| Toxicity/Toxicokinetics |
Toxicological data for Fmoc-HoArg(Pbf)-OH as a standalone compound are not extensively documented. The compound is intended for research use only and is not approved for human or veterinary use. Standard safety precautions should be observed when handling this compound, including the use of appropriate personal protective equipment. As a protected amino acid derivative, comprehensive toxicological studies have not been published. For peptides synthesized using this building block, standard toxicological assessments would be performed on the final peptide product rather than on the individual amino acid building block.
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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-HoArg(Pbf)-OH (CAS#: 1159680-21-3) has a molecular formula of C₃₅H₄₂N₄O₇S and a molecular weight of 662.80 g/mol. Its IUPAC name is (2S)-6-[[amino-[(2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-yl)sulfonylamino]methylidene]amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)hexanoic acid. The compound is also known as Fmoc-Nω-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-L-homoarginine. It is a white to off-white crystalline powder. The Pbf group provides orthogonal protection of the guanidino moiety, ensuring selective deprotection during SPPS cycles. The compound can be used in exactly the same manner as Fmoc-Arg(Pbf)-OH for introducing homoarginine into peptides. This compound is not a drug and has not undergone clinical trials or received regulatory approval for therapeutic use; it is strictly a research reagent.
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| Molecular Formula |
C35H42N4O7S
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|---|---|
| Molecular Weight |
662.80
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| Exact Mass |
662.277
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| CAS # |
1159680-21-3
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| PubChem CID |
46735199
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| Appearance |
White to off-white solid powder
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| LogP |
7.643
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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 |
13
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| Heavy Atom Count |
47
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| Complexity |
1230
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| Defined Atom Stereocenter Count |
1
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| SMILES |
CC1=C(C(=C(C2=C1OC(C2)(C)C)C)S(=O)(=O)NC(=NCCCC[C@@H](C(=O)O)NC(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35)N)C
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| InChi Key |
DOGZBRBJANHMLA-LJAQVGFWSA-N
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| InChi Code |
InChI=1S/C35H42N4O7S/c1-20-21(2)31(22(3)27-18-35(4,5)46-30(20)27)47(43,44)39-33(36)37-17-11-10-16-29(32(40)41)38-34(42)45-19-28-25-14-8-6-12-23(25)24-13-7-9-15-26(24)28/h6-9,12-15,28-29H,10-11,16-19H2,1-5H3,(H,38,42)(H,40,41)(H3,36,37,39)/t29-/m0/s1
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| Chemical Name |
(2S)-6-[[amino-[(2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-yl)sulfonylamino]methylidene]amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)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) |
DMSO: 125 mg/mL (188.59 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (3.14 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 (3.14 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.5088 mL | 7.5438 mL | 15.0875 mL | |
| 5 mM | 0.3018 mL | 1.5088 mL | 3.0175 mL | |
| 10 mM | 0.1509 mL | 0.7544 mL | 1.5088 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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