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Fmoc-Glu-OMe

Cat No.:V43610 Purity: ≥98%
Fmoc-Glu-OMe is a glutamic acid analogue that displays anti-bacterial effect and gelling properties in AgNO3 solutions.
Fmoc-Glu-OMe
Fmoc-Glu-OMe Chemical Structure CAS No.: 145038-49-9
Product category: New3
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Fmoc-Glu-OMe is a glutamic acid analogue that displays anti-bacterial effect and gelling properties in AgNO3 solutions. Fmoc-Glu-OMe is a formable wound healing biomaterial.
Fmoc-Glu-OMe is a protected amino acid derivative used in peptide synthesis. It is N-fluorenylmethoxycarbonyl-L-glutamic acid α-methyl ester. The compound has the molecular formula C21H21NO6 and a molecular weight of approximately 383.40 g/mol. Fmoc-Glu-OMe contains an Fmoc (9-fluorenylmethoxycarbonyl) protecting group on the amino group and a methyl ester protecting group on the α-carboxylic acid. The Fmoc group is widely used in solid-phase peptide synthesis as it can be removed under mild basic conditions (piperidine). The methyl ester protects the α-carboxylic acid during peptide synthesis and can be removed by hydrolysis. Glutamic acid is a polar amino acid that plays important roles in protein structure and function, and is a precursor to the neurotransmitter glutamate. The compound is used as a building block for the incorporation of glutamic acid into peptides and peptide-like molecules. The compound is intended for research use only and is not approved for clinical use. It is typically stored at -20°C and protected from moisture.
Biological Activity I Assay Protocols (From Reference)
Targets
Fmoc-Glu-OMe does not have a specific pharmacological target as it is a protected amino acid derivative used as a synthetic intermediate. Its function is to serve as a building block for the synthesis of peptides and peptide-like molecules. The Fmoc protecting group is used to selectively protect the amine functionality during peptide synthesis, allowing for the controlled assembly of peptide chains. The methyl ester protecting group protects the α-carboxylic acid, allowing for selective deprotection and functionalization. Glutamic acid is an important amino acid that is involved in various biological processes including protein synthesis, neurotransmission, and metabolism. The compound is used in medicinal chemistry for the synthesis of peptide-based drugs and chemical probes. The compound's utility lies in its role as a synthetic intermediate rather than as a bioactive molecule itself.
ln Vitro
In vitro, Fmoc-Glu-OMe is used as a synthetic intermediate in peptide synthesis. The compound is used to incorporate glutamic acid into peptides and peptide-like molecules using solid-phase peptide synthesis. In SPPS, the compound is coupled to a resin-bound peptide chain using standard coupling reagents such as HATU, HOBt, or DIC. The Fmoc protecting group is removed using piperidine to expose the amine for the next coupling step. The methyl ester protecting group can be removed by hydrolysis to yield the free carboxylic acid. Glutamic acid-containing peptides are important for various biological functions and are used in drug discovery and chemical biology. The compound's purity and identity are confirmed by HPLC and NMR spectroscopy. The compound is typically stored at -20°C and protected from moisture.
ln Vivo
In vivo, Fmoc-Glu-OMe is not used as a therapeutic agent but as a synthetic intermediate for the preparation of peptide-based compounds. The compound itself is not biologically active and is used solely as a chemical building block. The compound may be used in the synthesis of peptide drugs or chemical probes that contain glutamic acid residues. Glutamic acid is an important amino acid that is involved in various biological processes including protein synthesis, neurotransmission, and metabolism. However, Fmoc-Glu-OMe is a protected precursor that requires deprotection to yield the active peptide. The compound is intended for research use only and is not approved for clinical use. Its role is limited to chemical synthesis and drug discovery.
Enzyme Assay
In vitro synthetic procedures using Fmoc-Glu-OMe typically involve solid-phase peptide synthesis techniques. The compound is dissolved in appropriate solvents such as DMF or NMP for coupling reactions. In SPPS, the compound is activated using coupling reagents such as HATU, HOBt, or DIC and coupled to resin-bound peptides. The Fmoc protecting group is removed using 20% piperidine in DMF. The methyl ester protecting group is typically removed by hydrolysis using base such as NaOH or LiOH. The compound's purity and identity are confirmed by HPLC and mass spectrometry. The compound is typically stored at -20°C and protected from moisture. For long-term storage, the compound should be kept in a dry place and protected from light.
Cell Assay
Cell-based assays using Fmoc-Glu-OMe are not typical as the compound is a synthetic intermediate rather than a bioactive molecule. However, the compound may be used to synthesize peptides that are tested in cell-based assays. The compound itself would not be expected to have significant biological activity due to the presence of the protecting groups. For studies involving glutamic acid-containing peptides, the protected compound would be used in peptide synthesis, and the final peptide would be deprotected before testing. The compound's solubility in organic solvents makes it suitable for use in peptide synthesis. The compound is not typically used directly in cell culture experiments. Its role is limited to chemical synthesis and drug discovery.
Animal Protocol
In vivo animal experiments using Fmoc-Glu-OMe are not typical as the compound is a synthetic intermediate rather than a therapeutic agent. The compound may be used in the synthesis of peptide-based drugs that are subsequently tested in animal models. The compound itself is not administered to animals for therapeutic purposes. Its role is limited to chemical synthesis and drug discovery. The compound's pharmacokinetic and toxicity properties have not been characterized as it is not intended for in vivo use. The compound is intended for research use only and is not approved for clinical use. Standard laboratory safety precautions should be followed when handling the compound.
ADME/Pharmacokinetics
Fmoc-Glu-OMe has a molecular weight of approximately 383.40 g/mol and the formula C21H21NO6. The compound is soluble in organic solvents such as DMF, NMP, and DCM. For long-term storage, the compound is kept at -20°C in a dry place, protected from moisture. The compound is stable under normal storage conditions. The Fmoc protecting group can be removed under basic conditions (piperidine), and the methyl ester can be removed by hydrolysis. The compound is used as a building block in solid-phase peptide synthesis. Its purity and identity are confirmed by HPLC and NMR spectroscopy. The compound is intended for research use only and is not approved for clinical use.
Toxicity/Toxicokinetics
The toxicity of Fmoc-Glu-OMe has not been extensively characterized as the compound is a synthetic intermediate rather than a therapeutic agent. The compound is intended for research use only and is not for human use. Standard laboratory safety precautions should be followed when handling the compound, including the use of gloves and eye protection. The compound may cause irritation to skin, eyes, and respiratory tract upon contact. Inhalation of dust should be avoided. The compound is not classified as a highly toxic substance but should be handled with appropriate care. Safety data sheets recommend standard handling procedures for research chemicals. The compound's toxicity in vivo has not been studied as it is not intended for in vivo use. The compound should be handled in a well-ventilated area.
Additional Infomation
Fmoc-Glu-OMe (CAS 145038-49-9) is a protected amino acid derivative used in peptide synthesis. It is N-fluorenylmethoxycarbonyl-L-glutamic acid α-methyl ester. The compound has the molecular formula C21H21NO6 and a molecular weight of approximately 383.40 g/mol. Fmoc-Glu-OMe contains an Fmoc (9-fluorenylmethoxycarbonyl) protecting group on the amino group and a methyl ester protecting group on the α-carboxylic acid. The Fmoc group is widely used in solid-phase peptide synthesis as it can be removed under mild basic conditions (piperidine). The methyl ester protects the α-carboxylic acid during peptide synthesis and can be removed by hydrolysis. Glutamic acid is a polar amino acid that plays important roles in protein structure and function, and is a precursor to the neurotransmitter glutamate. The compound is used as a building block for the incorporation of glutamic acid into peptides and peptide-like molecules. The compound is soluble in organic solvents such as DMF, NMP, and DCM. It is intended for research use only and is not approved for clinical use. It is typically stored at -20°C and protected from moisture.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C21H21NO6
Molecular Weight
383.3945
Exact Mass
383.137
CAS #
145038-49-9
PubChem CID
53860042
Appearance
White to off-white solid powder
LogP
3.135
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
9
Heavy Atom Count
28
Complexity
557
Defined Atom Stereocenter Count
1
SMILES
O(C(N([H])[C@]([H])(C(=O)OC([H])([H])[H])C([H])([H])C([H])([H])C(=O)O[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
InChi Key
GVVDKFNHFXLOQY-SFHVURJKSA-N
InChi Code
InChI=1S/C21H21NO6/c1-27-20(25)18(10-11-19(23)24)22-21(26)28-12-17-15-8-4-2-6-13(15)14-7-3-5-9-16(14)17/h2-9,17-18H,10-12H2,1H3,(H,22,26)(H,23,24)/t18-/m0/s1
Chemical Name
(4S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-5-methoxy-5-oxopentanoic 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 2.6083 mL 13.0416 mL 26.0831 mL
5 mM 0.5217 mL 2.6083 mL 5.2166 mL
10 mM 0.2608 mL 1.3042 mL 2.6083 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)
  • Click the “Calculate” button
  • 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)
  • Click the “Calculate” button
  • 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:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • 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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