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Fmoc-Glu-Oall

Cat No.:V35869 Purity: ≥98%
Fmoc-Glu-OAll is a glutamic acid analogue.
Fmoc-Glu-Oall
Fmoc-Glu-Oall Chemical Structure CAS No.: 144120-54-7
Product category: Peptides
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
10g
Other Sizes
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Product Description
Fmoc-Glu-OAll is a glutamic acid analogue.
Fmoc-Glu-Oall (N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-glutamic acid 1-allyl ester, CAS 144120-54-7) is a protected derivative of the amino acid L-glutamic acid. It features a 9-fluorenylmethyloxycarbonyl (Fmoc) group protecting the α-amino group and an allyl (Oall) ester protecting the α-carboxyl group. With a molecular formula of C₂₃H₂₃NO₆ and a molecular weight of approximately 409.43 g/mol, this compound is a building block in Fmoc-based peptide synthesis. The allyl ester is an orthogonal protecting group that can be selectively removed under mild conditions using palladium catalysts (e.g., Pd(PPh₃)₄ in the presence of a nucleophile), allowing for selective deprotection in the presence of other acid- or base-labile protecting groups.
Biological Activity I Assay Protocols (From Reference)
Targets
Fmoc-Glu-Oall does not have a specific biological target. Its primary utility is as a chemical building block in organic synthesis, particularly in Fmoc-based peptide synthesis. The compound serves as a protected glutamic acid unit that can be incorporated into peptide chains while the Fmoc and allyl groups protect the amino and α-carboxyl groups, respectively, from unwanted reactions. Glutamic acid is a neurotransmitter and metabolic intermediate, but in its protected form, the compound is not designed to interact with biological receptors or enzymes. Its value lies in its chemical properties as a synthetic intermediate, enabling the construction of complex peptides and pharmaceutical compounds.
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].
Fmoc-Glu-Oall does not exhibit pharmacological activity in vitro. As a protected amino acid derivative, it is a synthetic intermediate rather than a bioactive compound. In vitro studies using this compound focus on its chemical reactivity, such as its use in peptide bond formation reactions and selective deprotection strategies, rather than assessments of pharmacological activity. The compound may be used as a substrate in enzymatic assays to study the cleavage of protecting groups, but these are analytical applications. The compound does not bind to receptors, inhibit enzymes, or produce cytotoxic effects in cell-based assays at concentrations typically used for synthesis. Its role in research is almost exclusively as a reagent for organic synthesis.
ln Vivo
Fmoc-Glu-Oall is not a pharmacologically active compound and therefore does not have defined in vivo activity as a drug. When administered to animals, the compound would likely be metabolized to release glutamic acid, which would then enter normal metabolic pathways. However, the compound is not used therapeutically, and its in vivo effects would be limited to those of the released glutamic acid. Its primary value remains in synthetic chemistry, where it serves as a building block for the preparation of peptides and pharmaceutical compounds.
Enzyme Assay
In vitro assays for Fmoc-Glu-Oall are primarily focused on its chemical properties and reactivity rather than biological activity. Standard protocols in Fmoc-based solid-phase peptide synthesis involve the use of this compound as a protected glutamic acid building block with an orthogonal allyl ester. The compound is typically dissolved in polar aprotic solvents such as DMF or DCM and coupled to a growing peptide chain on a solid support using standard peptide coupling reagents. The progress of the coupling reaction can be monitored by HPLC or TLC. The Fmoc group can be removed under basic conditions (e.g., 20% piperidine in DMF), and the allyl ester can be selectively removed using palladium catalysts (e.g., Pd(PPh₃)₄) in the presence of a nucleophile, revealing the free carboxyl group for further functionalization.
Cell Assay
In vitro cellular assays using Fmoc-Glu-Oall are not commonly performed because the compound lacks intrinsic biological activity. The compound is used exclusively in synthetic chemistry applications and is not designed for cell culture studies. Its use is confined to the laboratory, where it serves as a building block for the preparation of peptides and pharmaceutical compounds.
Animal Protocol
In vivo animal studies with Fmoc-Glu-Oall are not typically conducted, as the compound is a synthetic intermediate rather than a pharmacologically active agent. If used in vivo, the compound would be administered to animals to study the metabolism of protected amino acid derivatives. However, such studies are rare, and the compound is generally used exclusively in synthetic chemistry applications. Its use is confined to the laboratory, where it serves as a building block for the preparation of peptides and pharmaceutical compounds.
ADME/Pharmacokinetics
Fmoc-Glu-Oall is not a drug candidate, and pharmacokinetic data are not available. As a protected amino acid derivative, it is designed for chemical synthesis rather than systemic administration. If administered in vivo, the compound would likely be hydrolyzed to release glutamic acid. The compound's pharmacokinetic properties have not been characterized, and its use is confined to in vitro synthetic applications.
Toxicity/Toxicokinetics
The compound is generally considered to have low toxicity, consistent with its use as a chemical reagent. The compound should be stored at -20°C for long-term stability. Standard laboratory safety precautions, including the use of personal protective equipment, are recommended. It is not classified as a highly toxic substance, but appropriate safety measures should be followed. Inhalation, ingestion, or skin contact should be avoided.
References

[1]. Effects of amino acid derivatives on physical, mental, and physiological activities. Crit Rev Food Sci Nutr. 2015;55(13):1793-1144.

Additional Infomation
Fmoc-Glu-Oall (N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-glutamic acid 1-allyl ester, CAS 144120-54-7) is a protected amino acid derivative used as a building block in peptide synthesis. Its chemical formula is C₂₃H₂₃NO₆ and molecular weight is approximately 409.43 g/mol. The compound features an Fmoc-protected amino group and an allyl ester-protected α-carboxyl group. It is intended for research use only and is not for human therapeutic applications. The compound is typically stored at -20°C for long-term stability.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C23H23NO6
Molecular Weight
409.4318
Exact Mass
409.153
CAS #
144120-54-7
PubChem CID
7020606
Appearance
White to off-white solid powder
Density
1.264g/cm3
Boiling Point
652.3ºC at 760 mmHg
Melting Point
118-122ºC
Flash Point
348.3ºC
Vapour Pressure
6.64E-18mmHg at 25°C
Index of Refraction
1.585
LogP
3.878
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
11
Heavy Atom Count
30
Complexity
613
Defined Atom Stereocenter Count
1
SMILES
C=CCOC(=O)[C@H](CCC(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
InChi Key
ORKKMGRINLTBPC-FQEVSTJZSA-N
InChi Code
InChI=1S/C23H23NO6/c1-2-13-29-22(27)20(11-12-21(25)26)24-23(28)30-14-19-17-9-5-3-7-15(17)16-8-4-6-10-18(16)19/h2-10,19-20H,1,11-14H2,(H,24,28)(H,25,26)/t20-/m0/s1
Chemical Name
(4S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-5-oxo-5-prop-2-enoxypentanoic acid
HS Tariff Code
2934.99.9001
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)
Solubility Data
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
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
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*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 : PEG300Tween 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).
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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)]
*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.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL 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).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.4424 mL 12.2121 mL 24.4242 mL
5 mM 0.4885 mL 2.4424 mL 4.8848 mL
10 mM 0.2442 mL 1.2212 mL 2.4424 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.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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