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Fmoc-L-Valine (Fmoc-Val-OH) is a protected form of the amino acid L-Valine, used as a building block in solid-phase peptide synthesis. The Fmoc group protects the amine functionality (-NH₂), preventing unwanted reactions during the stepwise chemical assembly of peptides. This allows the free carboxylic acid (-OH) to form peptide bonds with the next amino acid in the sequence. The Fmoc group is later removed with a mild base. It is essential for creating custom peptides in pharmaceutical research, drug development, and biochemical studies.
Items | Specification | Result |
Appearance | White powder | Complies |
Purity (HPLC) | ≥99% | 99.66% |
TLC | ≥98% | >98% |
Melting point | 140-155℃ | 151.1-152.1℃ |
Loss on drying | ≤2.0% | 0.11% |
Water content | ≤1.0% | 0.04% |
Product parameters | |
Cas number: | 68858-20-8 |
Appearance: | White powder |
Purity: | 99%min |
MOQ: | 1kg |
Price: | Negotiable |
Package details: | 1kg/foil bag;25kg/drum |
Brand: | Fortunachem |
Fmoc-L-Valine (chemical name: *N-(9-Fluorenylmethoxycarbonyl)-L-valine*, often abbreviated as Fmoc-Val-OH) is a specially modified, protected form of the amino acid L-Valine (Val). It is not a drug or a naturally occurring substance but is an essential building block and reagent used in the field of solid-phase peptide synthesis (SPPS).
Its name breaks down into its components:
Valine (Val): A essential, hydrophobic (water-repelling) amino acid with a branched side chain (isopropyl group).
L-: This denotes the specific natural stereochemistry (three-dimensional orientation) of the amino acid, which is crucial for its biological activity.
Fmoc: Stands for 9-Fluorenylmethoxycarbonyl. This is a protecting group covalently attached to valine's alpha-amine group (-NH₂).
-OH: Indicates that the carboxylic acid group (-COOH) remains free and reactive.
In simple terms, it is a valine molecule that has been "packaged" for controlled use in a chemical assembly line.
The sole purpose of Fmoc-L-Valine is to be used as a single, precise component for manually constructing peptide chains, one amino acid at a time, in a laboratory setting.
The Problem in Peptide Synthesis:
To form a peptide bond, the amine group of one amino acid must react with the carboxylic acid group of another. If both groups on a single amino acid were free, it would react with itself and other molecules uncontrollably, creating a useless mixture.
The Solution with Fmoc-L-Valine:
The Fmoc group acts as a temporary protective cap on valine's amine group. This prevents it from reacting prematurely, allowing chemists to control the order in which amino acids are added to a growing chain.
How it's Used (The SPPS Cycle):
In automated peptide synthesizers, the process for adding Fmoc-L-Valine is part of a repeating cycle:
Deprotection: The Fmoc group is removed from the last amino acid attached to a solid resin bead using a mild base (like piperidine), exposing its reactive amine group.
Coupling: Fmoc-L-Valine, along with activating agents, is delivered to the reaction vessel. The exposed amine group attacks the highly reactive carboxylic acid group of the Fmoc-L-Valine, forming a new peptide bond and adding a valine residue to the chain.
Washing: Excess reagents and byproducts are washed away.
This cycle repeats for each amino acid in the desired sequence.
Orthogonal Protection: The Fmoc group is stable under acidic conditions but is easily and cleanly removed by a mild base. This is critical because it allows the Fmoc group (on the amine) to be removed without affecting other permanent protecting groups that may be on the side chains of other amino acids (e.g., on lysine or aspartic acid).
Hydrophobicity: Valine's isopropyl side chain makes Fmoc-L-Valine quite hydrophobic. This property can influence the solubility of the growing peptide chain during synthesis and must be accounted for by the chemist.
UV Activity: The Fmoc group absorbs ultraviolet (UV) light strongly. This property is harnessed to monitor the efficiency of the deprotection step in real-time during synthesis.
High Purity: For successful peptide synthesis, Fmoc-L-Valine must be of very high purity to ensure near-perfect coupling efficiency and prevent errors in the final peptide sequence.
Fmoc-L-Valine is a fundamental tool in:
Pharmaceutical Development: Synthesizing peptide-based drugs and drug candidates for a wide range of diseases.
Academic Research: Creating specific peptide sequences to study protein folding, function, and interactions.
Biotechnology: Designing and producing peptides for use in diagnostics, vaccines, and novel biomaterials.
In summary, Fmoc-L-Valine is a protected, synthetic version of the amino acid valine designed specifically for the machine-assisted, step-by-step construction of custom peptides, which are vital for modern medical and biochemical research.
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