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Boc-Nva-OH

Boc-Nva-OH is a valine analogue.
Boc-Nva-OH
Boc-Nva-OH Chemical Structure CAS No.: 53308-95-5
Product category: Amino Acid Derivatives
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
25g
50g
Other Sizes
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Product Description
Boc-Nva-OH is a valine analogue.
Boc-Nva-OH (CAS#: 53308-95-5), also known as N-(tert-Butoxycarbonyl)-L-norvaline or N-Boc-L-norvaline, is a protected non-proteinogenic amino acid. With a molecular formula of C₁₀H₁₉NO₄ and a molecular weight of 217.27 g/mol, it appears as a white to light yellow powder to crystal with a melting point of 64.0 to 69.0°C. The compound features a tert-butyloxycarbonyl (Boc) protecting group attached to the amino function of L-norvaline, which is removable under acidic conditions (typically TFA). Norvaline, an isomer of valine with a four-carbon aliphatic side chain, is a non-proteinogenic amino acid that is incorporated into peptides to study steric effects and structure-activity relationships. Boc-Nva-OH serves as a standard building block for introducing norvaline amino-acid residues by Boc solid-phase peptide synthesis (SPPS). The compound is widely utilized in peptide synthesis and drug development, particularly for creating modified peptides and peptidomimetics. It is commercially available from various suppliers with purity typically ≥98% (HPLC). The product is typically stored at 2-8°C. The compound has a specific optical rotation α 25/D (c=2 in methanol) of -16.5 to -13.5° and is clearly soluble at 1 mmole in 2 ml DMF.
Biological Activity I Assay Protocols (From Reference)
Targets
Boc-Nva-OH, as a synthetic intermediate, has no biological target. Its role is to provide norvaline residues in peptide chains. It does not interact with enzymes or receptors in pharmacological assays. Its "target" is the peptide coupling reaction, where it acts as a protected amino acid donor. The presence of L-norvaline introduces a four-carbon aliphatic side chain into the peptide structure, which can significantly alter the peptide's physicochemical properties and biological activity compared to valine-containing peptides. The Boc protecting group strategy enables selective reactions during peptide chain assembly, preventing unwanted side reactions. The compound's utility lies entirely in the chemical synthesis domain rather than in pharmacological evaluation. In solid-phase peptide synthesis, the Boc group is typically removed with TFA between coupling steps, allowing for the controlled assembly of peptide chains.
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].
The in vitro activity of Boc-Nva-OH is measured by coupling efficiency in solid-phase or solution-phase synthesis. Typically, it reacts with resin-bound or free amines using standard coupling reagents such as HBTU/HOBt/DIEA. Coupling yields >90% are common with this building block. Purity is assessed by HPLC (typically ≥98%) and TLC. No inherent biological activity is observed as the compound is a protected amino acid derivative intended for synthetic purposes. The compound's reactivity is characterized by the successful formation of peptide bonds with various amino acid derivatives under standard SPPS conditions. Quality control includes assessment of appearance (white to slight yellow to beige powder), identity (IR), optical rotation, purity by TLC (≥98%), and solubility in DMF. The compound is a standard building block for Boc SPPS.
ln Vivo
In vivo activity is not applicable for Boc-Nva-OH. The compound is not used in animals and is a research chemical for laboratory synthesis only. It is not intended for therapeutic or diagnostic purposes. Any biological activity that might be observed would be a result of metabolic conversion following deprotection, but such studies are not typically conducted with this protected amino acid. Its utility lies entirely in the chemical synthesis domain rather than in pharmacological evaluation. The compound is stored and handled under standard laboratory conditions for chemical synthesis.
Enzyme Assay
The in vitro enzyme/receptor binding (non-cellular) experimental workflow for Boc-Nva-OH involves standard peptide synthesis and characterization procedures. A typical workflow: dissolve Boc-Nva-OH (1 equiv.) in DMF, add HBTU (1.1 equiv.), HOBt (1.1 equiv.), and DIEA (2 equiv.), then add amine component. Stir at room temperature for 2-3 hours. Monitor by TLC (ninhydrin). After work-up, purify by flash chromatography. Characterize by ¹H-NMR (Boc tert-butyl at δ 1.4, norvaline side chain) and MS ([M+H]⁺). The compound's use as a standard building block for introduction of norvaline amino-acid residues by Boc SPPS is well established. Associated protocols and technical articles for cleavage and deprotection protocols for Boc SPPS are available. TLC solvent systems for Novabiochem products are documented. The compound has an optical rotation α 25/D (c=2 in methanol) of -16.5 to -13.5°.
Cell Assay
In vitro cell-based experimental workflows are not performed on Boc-Nva-OH. The deprotected norvaline-containing peptides may be tested in cell viability or receptor binding assays, but the protected compound itself is not used in cell-based systems. The compound is strictly a synthetic intermediate and is not intended for biological activity screening. When incorporated into peptides, the final deprotected products may be subjected to standard cell-based assays including cell viability (MTT assay), apoptosis detection, or receptor binding studies depending on the biological target of the synthesized peptide. However, these assays are performed on the final peptide products rather than the protected amino acid building block.
Animal Protocol
In vivo animal experiments are not relevant for Boc-Nva-OH. The compound is a synthetic intermediate and is not used in animal models. It is stored at 2-8°C. The compound is not formulated for any route of administration. Any in vivo studies would involve the final deprotected peptide products rather than the protected amino acid itself.
ADME/Pharmacokinetics
The pharmacokinetic properties of Boc-Nva-OH have not been characterized. The compound is not a drug. It has moderate lipophilicity (LogP ~1.5) but no ADME data are available. The compound is stable under recommended storage conditions. If administered, the Boc protecting group would likely be cleaved metabolically, releasing norvaline, but such studies are not conducted with this protected amino acid. No data on absorption, distribution, metabolism, or excretion are available for the protected form.
Toxicity/Toxicokinetics
The toxicological data for Boc-Nva-OH are limited. Standard precautions apply: it may cause skin and eye irritation, avoid dust inhalation. No chronic, carcinogenic, or reproductive toxicity studies exist because it is not a pharmaceutical. Handle in fume hood with appropriate personal protective equipment. Not approved for human or veterinary use. The compound is intended for research use only.
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
Boc-Nva-OH is a common reagent for introducing norvaline into peptides. It is a standard building block for introduction of norvaline amino-acid residues by Boc SPPS. The compound is commercially available from multiple suppliers including Novabiochem®. It is not a drug and has no clinical status. The compound has a purity of ≥98% (TLC) and is available in powder form. The product line is Novabiochem® and the manufacturer/tradename is Novabiochem®. The compound is used in peptide synthesis applications. Replaces: 04-12-0107. Novabiochem is a registered trademark of Merck KGaA. The compound has a storage temperature of 2-8°C. The compound is classified as WGK 3.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C10H19NO4
Molecular Weight
217.26
Exact Mass
217.131
CAS #
53308-95-5
PubChem CID
2733748
Appearance
White to off-white solid powder
Density
1.1±0.1 g/cm3
Boiling Point
348.3±25.0 °C at 760 mmHg
Melting Point
43-47ºC
Flash Point
164.4±23.2 °C
Vapour Pressure
0.0±1.6 mmHg at 25°C
Index of Refraction
1.462
LogP
2.16
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
6
Heavy Atom Count
15
Complexity
232
Defined Atom Stereocenter Count
1
SMILES
CCC[C@@H](C(=O)O)NC(=O)OC(C)(C)C
InChi Key
INWOAUUPYIXDHN-ZETCQYMHSA-N
InChi Code
InChI=1S/C10H19NO4/c1-5-6-7(8(12)13)11-9(14)15-10(2,3)4/h7H,5-6H2,1-4H3,(H,11,14)(H,12,13)/t7-/m0/s1
Chemical Name
(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic 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 4.6028 mL 23.0139 mL 46.0278 mL
5 mM 0.9206 mL 4.6028 mL 9.2056 mL
10 mM 0.4603 mL 2.3014 mL 4.6028 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:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
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:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
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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