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Fmoc-Nva-OH

Alias: (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)pentanoic acid; Fmoc-Nva-OH
Cat No.:V37485 Purity: ≥98%
(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)pentanoic acid is a valine analogue.
Fmoc-Nva-OH
Fmoc-Nva-OH Chemical Structure CAS No.: 135112-28-6
Product category: Amino Acids
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)pentanoic acid is a valine analogue.
Fmoc-Nva-OH is an Fmoc-protected amino acid derivative of L-norvaline, a valine analogue. It is used as a standard building block in Fmoc-based solid-phase peptide synthesis (SPPS) for the introduction of norvaline residues into peptide sequences. The compound has a molecular weight of 339.39 g/mol and formula C₂₀H₂₁NO₄. It appears as a white to off-white powder with a melting point of 151-157°C. Fmoc-Nva-OH is a key reagent in peptide chemistry research.
Biological Activity I Assay Protocols (From Reference)
Targets
Fmoc-Nva-OH is classified as an amino acid derivative with applications in peptide synthesis. It does not have a specific biological receptor target; rather, it functions as a protecting group reagent for introducing norvaline into synthetic peptides. The Fmoc group protects the amino group during chain assembly and is removed under mild basic conditions. The norvaline residue can affect peptide conformation and biological activity when incorporated into bioactive sequences.
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-Nva-OH is primarily as a peptide synthesis reagent. Amino acids and amino acid derivatives have been commercially used as ergogenic supplements. They affect the release of anabolic hormones, the availability of fuel for activity, and mental performance under pressure. Fmoc-Nva-OH itself is not biologically active in cell-based assays; its utility is in the preparation of norvaline-containing peptides for subsequent biological evaluation.
ln Vivo
There is no specific in vivo activity data for Fmoc-Nva-OH as it is a protected amino acid building block used in research. The compound is not administered in vivo in its intact form. Peptides incorporating norvaline residues synthesized using Fmoc-Nva-OH may be evaluated in animal models for various biological activities depending on the peptide sequence. Norvaline is a non-proteinogenic amino acid that can be used to probe enzyme specificity and protein function in vivo.
Enzyme Assay
Standard protocols for Fmoc-amino acids involve activation and coupling in SPPS. Fmoc-Nva-OH (0.5-1.0 mmol) is dissolved in DMF with coupling reagents such as HATU or HBTU (0.95-1.0 equiv) and DIPEA (2.0-2.5 equiv). The activated solution is added to the resin-bound peptide and agitated for 1-2 hours. Coupling completion is monitored by Kaiser test or HPLC. Deprotection of the Fmoc group is achieved with 20% piperidine in DMF (2 × 5-10 min). Purity is verified by HPLC (≥98%).
Cell Assay
In vitro cell-based assays using Fmoc-Nva-OH are not applicable as it is a peptide synthesis building block, not a cell-permeable compound. However, norvaline-containing peptides synthesized with this reagent can be tested in cell culture. Peptides are dissolved in DMSO or cell culture medium, filtered sterile, and added to cells at concentrations ranging from 0.1-100 µM. Cells are incubated for 24-72 hours, and endpoints such as cell viability, proliferation, or signaling pathway activation are measured using standard assays.
Animal Protocol
Animal studies with Fmoc-Nva-OH are not conducted as the compound is a research reagent. Norvaline-containing peptides synthesized using this building block may be evaluated in vivo. Typical protocols involve administration of the peptide in appropriate formulations via injection or oral gavage. Blood samples are collected for PK analysis, and tissues are harvested for histopathological or biomarker analysis. Dosing regimens depend on the peptide's intended therapeutic application and are determined empirically.
ADME/Pharmacokinetics
Pharmacokinetic properties of Fmoc-Nva-OH are not applicable to the compound itself as it is not a drug. The compound has a molecular weight of 339.39 g/mol, formula C₂₀H₂₁NO₄, and LogP of 4.61. It is soluble in DMF and other organic solvents for peptide synthesis. The Fmoc group is removed under basic conditions during synthesis. The resulting norvaline-containing peptides may have altered PK properties due to the non-natural amino acid residue, potentially affecting metabolic stability and bioavailability.
Toxicity/Toxicokinetics
Limited toxicity data is available for Fmoc-Nva-OH as it is a research chemical. Standard laboratory safety practices should be followed when handling. The compound is not intended for human use. Acute toxicity is expected to be low. The compound should be stored as a powder at -20°C for up to 3 years or at 4°C for up to 2 years. In solvent, it can be stored at -80°C for 6 months or at -20°C for 1 month. Proper personal protective equipment should be worn.
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.
Additional Infomation
Fmoc-Nva-OH (CAS#: 135112-28-6) is also known as (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)pentanoic acid and Fmoc-L-norvaline. Its molecular weight is 339.39 and formula is C₂₀H₂₁NO₄. The compound has a purity of ≥98% by HPLC and an optical rotation of -22 to -18° (c=2, DMF). It is a standard reagent for solid-phase peptide synthesis. It has no approved therapeutic indications and is not in clinical trials.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C20H21NO4
Molecular Weight
339.38504
Exact Mass
339.147
CAS #
135112-28-6
PubChem CID
7016885
Appearance
White to off-white powder
Density
1.2±0.1 g/cm3
Boiling Point
557.9±33.0 °C at 760 mmHg
Melting Point
151-153ºC
Flash Point
291.2±25.4 °C
Vapour Pressure
0.0±1.6 mmHg at 25°C
Index of Refraction
1.591
LogP
4.61
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
7
Heavy Atom Count
25
Complexity
458
Defined Atom Stereocenter Count
1
SMILES
CCC[C@H](NC(OCC1C2=CC=CC=C2C3=CC=CC=C31)=O)C(O)=O
InChi Key
JBIJSEUVWWLFGV-SFHVURJKSA-N
InChi Code
InChI=1S/C20H21NO4/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/h3-6,8-11,17-18H,2,7,12H2,1H3,(H,21,24)(H,22,23)/t18-/m0/s1
Chemical Name
(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)pentanoic acid
Synonyms
(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)pentanoic acid; Fmoc-Nva-OH
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 2.9465 mL 14.7323 mL 29.4646 mL
5 mM 0.5893 mL 2.9465 mL 5.8929 mL
10 mM 0.2946 mL 1.4732 mL 2.9465 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:
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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.

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  • 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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