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Fmoc-3-(2-Naphthyl)-L-alanine

Cat No.:V35827 Purity: ≥98%
Fmoc-2-Nal-OH is an alanine analogue.
Fmoc-3-(2-Naphthyl)-L-alanine
Fmoc-3-(2-Naphthyl)-L-alanine Chemical Structure CAS No.: 112883-43-9
Product category: Peptides
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Fmoc-2-Nal-OH is an alanine analogue.
Fmoc-3-(2-Naphthyl)-L-alanine (CAS 112883-43-9) is an Fmoc-protected derivative of the non-proteinogenic amino acid 3-(2-naphthyl)-L-alanine. With a molecular formula of C₂₈H₂₃NO₄ and a molecular weight of approximately 437.49 g/mol, this compound features a naphthyl group at the 2-position of the side chain. It is utilized in peptide synthesis as a building block for incorporating the 2-naphthylalanine residue. The Fmoc (9-fluorenylmethyloxycarbonyl) protecting group provides base-labile protection for the amino group, enabling selective deprotection during peptide chain assembly.
Biological Activity I Assay Protocols (From Reference)
Targets
Fmoc-3-(2-Naphthyl)-L-alanine does not have a specific biological target. Its primary utility is as a chemical building block in Fmoc-based peptide synthesis. The compound serves as a protected 3-(2-naphthyl)-L-alanine unit that can be incorporated into peptide chains. The naphthyl side-chain provides a large aromatic hydrophobic group that can be used to study peptide-protein interactions and to enhance peptide stability. In its protected form, the compound is not designed to interact with biological receptors or enzymes.
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-3-(2-Naphthyl)-L-alanine 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, rather than assessments of pharmacological activity. The compound may be used as a substrate in enzymatic assays to study the cleavage of Fmoc protecting groups, but these are analytical applications. Its role in research is almost exclusively as a reagent for organic synthesis.
ln Vivo
Fmoc-3-(2-Naphthyl)-L-alanine 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 3-(2-naphthyl)-L-alanine. However, the compound is not used therapeutically. 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-3-(2-Naphthyl)-L-alanine 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 amino acid building block. 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.
Cell Assay
In vitro cellular assays using Fmoc-3-(2-Naphthyl)-L-alanine 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-3-(2-Naphthyl)-L-alanine 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.
ADME/Pharmacokinetics
Fmoc-3-(2-Naphthyl)-L-alanine 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 metabolized to release 3-(2-naphthyl)-L-alanine. The compound's pharmacokinetic properties have not been characterized.
Toxicity/Toxicokinetics
The compound is generally considered to have low toxicity, consistent with its use as a chemical reagent. 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):1793-1053.

Additional Infomation
Fmoc-3-(2-Naphthyl)-L-alanine (CAS 112883-43-9) is an Fmoc-protected amino acid derivative used as a building block in peptide synthesis. Its molecular formula is C₂₈H₂₃NO₄ and its molecular weight is approximately 437.49 g/mol. The compound features an Fmoc-protected amino group and a 2-naphthyl side-chain. It is intended for research use only and is not for human therapeutic applications.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C28H23NO4
Molecular Weight
437.48652
Exact Mass
437.162
CAS #
112883-43-9
PubChem CID
2734452
Appearance
White to off-white solid powder
Density
1.3±0.1 g/cm3
Boiling Point
690.7±50.0 °C at 760 mmHg
Melting Point
155ºC
Flash Point
371.6±30.1 °C
Vapour Pressure
0.0±2.3 mmHg at 25°C
Index of Refraction
1.671
LogP
6.64
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
7
Heavy Atom Count
33
Complexity
673
Defined Atom Stereocenter Count
1
SMILES
C1=CC=C2C=C(C=CC2=C1)C[C@@H](C(=O)O)NC(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35
InChi Key
JYUTZJVERLGMQZ-SANMLTNESA-N
InChi Code
InChI=1S/C28H23NO4/c30-27(31)26(16-18-13-14-19-7-1-2-8-20(19)15-18)29-28(32)33-17-25-23-11-5-3-9-21(23)22-10-4-6-12-24(22)25/h1-15,25-26H,16-17H2,(H,29,32)(H,30,31)/t26-/m0/s1
Chemical Name
(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-naphthalen-2-ylpropanoic 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)
DMSO : ~100 mg/mL (~228.58 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2 mg/mL (4.57 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% 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 20.0 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 mg/mL (4.57 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 20.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.2858 mL 11.4288 mL 22.8577 mL
5 mM 0.4572 mL 2.2858 mL 4.5715 mL
10 mM 0.2286 mL 1.1429 mL 2.2858 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.

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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?
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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:
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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
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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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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