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| Other Sizes |
| Targets |
Fmoc-Pra-OH targets peptide synthesis and bioconjugation applications. The terminal alkyne side chain serves as a handle for click chemistry, allowing the introduction of various functionalities into peptides and proteins. As a glycine analogue, it can be incorporated into peptides via SPPS. The compound is used in the synthesis of bioconjugates and for studying protein interactions. Its mechanism of action is related to its role in CuAAC reactions.
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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].
In vitro activity of Fmoc-Pra-OH is primarily as a click chemistry reagent. The alkyne group can undergo CuAAC with azide-containing molecules to form stable triazole linkages. This enables the modification of peptides and proteins with various labels, probes, or functional groups. Amino acids and amino acid derivatives have been used as ergogenic supplements. Fmoc-Pra-OH itself is not directly biologically active; its utility is in bioconjugation applications. |
| ln Vivo |
There is no specific in vivo activity data for Fmoc-Pra-OH as a standalone compound. Peptides containing propargylglycine residues synthesized using this building block can be used for in vivo bioconjugation studies via click chemistry. The alkyne handle allows for the attachment of imaging agents, drugs, or other functional moieties to peptides for in vivo applications. Animal studies would be performed on the final conjugated products. Fmoc-Pra-OH is a research reagent.
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| Enzyme Assay |
In vitro enzyme/receptor binding protocols for Fmoc-Pra-OH involve its use as a click chemistry reagent. The compound can be incorporated into peptides via SPPS. Standard Fmoc chemistry: the compound is activated with coupling reagents and coupled to resin-bound peptides. The alkyne group is stable under standard peptide synthesis conditions. After peptide synthesis and deprotection, the alkyne-containing peptide can be reacted with azide-containing molecules in CuAAC reactions using copper sulfate and sodium ascorbate in aqueous buffers.
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| Cell Assay |
Cell-based protocols for Fmoc-Pra-OH involve its use in labeling and bioconjugation studies. Cells expressing azide-containing biomolecules (via metabolic labeling) can be treated with alkyne-containing probes synthesized using Fmoc-Pra-OH. The CuAAC reaction is performed on live or fixed cells. Alternatively, alkyne-containing peptides can be tested in cell culture for various biological activities. Peptides are dissolved in DMSO or appropriate buffers and added to cells at 0.1-100 µM.
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| Animal Protocol |
Animal studies with Fmoc-Pra-OH are not conducted directly. Peptides or biomolecules labeled via click chemistry using Fmoc-Pra-OH-derived alkyne handles may be evaluated in vivo. Protocols involve administration of the labeled compound via appropriate routes. Imaging or biodistribution studies can be performed depending on the label attached. The click chemistry approach enables site-specific labeling of biomolecules for in vivo tracking and targeting studies.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for Fmoc-Pra-OH is not applicable as it is a research building block. The compound has molecular weight 335.36 g/mol and formula C₂₀H₁₇NO₄. It is soluble in DMSO (100 mg/mL) and appears as a white to off-white powder. Store as powder at -20°C. The Fmoc group is removed under basic conditions during peptide synthesis. The alkyne handle is stable and available for click chemistry conjugation.
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| Toxicity/Toxicokinetics |
Toxicological data for Fmoc-Pra-OH is limited. The compound is for research use only. Standard safety precautions should be observed. Store as powder at -20°C for up to 3 years. Acute toxicity is expected to be low. Proper personal protective equipment should be worn when handling. No specific toxicity studies have been reported. It is not intended for human therapeutic use.
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| References | |
| Additional Infomation |
Fmoc-Pra-OH (CAS#: 198561-07-8) is also known as Fmoc-L-propargylglycine, (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)pent-4-ynoic acid. Its molecular formula is C₂₀H₁₇NO₄ and molecular weight is 335.36. It is a glycine analogue and click chemistry reagent containing an alkyne group. It is used in CuAAC reactions. It has no approved therapeutic indications.
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| Molecular Formula |
C20H17NO4
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|---|---|
| Molecular Weight |
335.3533
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| Exact Mass |
335.115
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| CAS # |
198561-07-8
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| PubChem CID |
2734461
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| Appearance |
White to off-white powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
576.7±50.0 °C at 760 mmHg
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| Melting Point |
175ºC
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| Flash Point |
302.6±30.1 °C
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| Vapour Pressure |
0.0±1.7 mmHg at 25°C
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| Index of Refraction |
1.619
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| LogP |
4.19
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
25
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| Complexity |
529
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| Defined Atom Stereocenter Count |
1
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| SMILES |
O(C(N([H])[C@]([H])(C(=O)O[H])C([H])([H])C#C[H])=O)C([H])([H])C1([H])C2=C([H])C([H])=C([H])C([H])=C2C2=C([H])C([H])=C([H])C([H])=C12
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| InChi Key |
DJGMNCKHNMRKFM-SFHVURJKSA-N
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| InChi Code |
InChI=1S/C20H17NO4/c1-2-7-18(19(22)23)21-20(24)25-12-17-15-10-5-3-8-13(15)14-9-4-6-11-16(14)17/h1,3-6,8-11,17-18H,7,12H2,(H,21,24)(H,22,23)/t18-/m0/s1
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| Chemical Name |
(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)pent-4-ynoic acid
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| Synonyms |
Fmoc-Pra-OH
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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 : ~100 mg/mL (~298.20 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: 2.5 mg/mL (7.45 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 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: ≥ 2.5 mg/mL (7.45 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 25.0 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: ≥ 2.5 mg/mL (7.45 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 | 2.9820 mL | 14.9098 mL | 29.8196 mL | |
| 5 mM | 0.5964 mL | 2.9820 mL | 5.9639 mL | |
| 10 mM | 0.2982 mL | 1.4910 mL | 2.9820 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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