Exploring the Chemical Properties of Fmoc-(S)-3-Amino-4-(2-fluorophenyl)butyric Acid
At NINGBO INNO PHARMCHEM CO.,LTD., we specialize in providing chemicals with well-defined properties that serve critical roles in research and development. Fmoc-(S)-3-Amino-4-(2-fluorophenyl)butyric Acid is a prime example of such a compound, offering a unique combination of structural features that make it highly valuable in organic synthesis, particularly within peptide chemistry and medicinal chemistry.
The core structure of this molecule is an amino acid derivative, specifically a butyric acid with an amino group at the alpha-position and a 2-fluorophenyl group at the beta-position. The chirality at the alpha-carbon (denoted by (S)) is crucial for its biological relevance, as it dictates the stereochemistry of the peptide chain it will be incorporated into. The presence of the 2-fluorophenyl substituent is significant; fluorine atoms are known to alter the electronic distribution and lipophilicity of organic molecules. The electronegativity of fluorine can influence the acidity of nearby protons and the reactivity of adjacent functional groups. The phenyl ring, substituted with fluorine, introduces aromaticity and further modifies the molecule's physical properties, such as solubility and potential for pi-stacking interactions.
A key feature is the Fmoc (9-fluorenylmethyloxycarbonyl) protecting group attached to the amino nitrogen. This group is a widely adopted orthogonal protecting group in peptide synthesis, particularly in solid-phase peptide synthesis (SPPS). The Fmoc group is stable under acidic conditions but is readily cleaved by mild bases, such as piperidine. This selective cleavage allows for the stepwise addition of amino acids to a growing peptide chain without affecting other protecting groups or the peptide backbone itself. The efficiency and mildness of Fmoc deprotection are critical for preserving the integrity of sensitive peptide sequences.
The chemical properties of Fmoc-(S)-3-Amino-4-(2-fluorophenyl)butyric Acid make it an excellent building block for several reasons. Its purity, typically exceeding 97%, ensures reliable reaction outcomes. Its physical form as a white solid or powder simplifies handling and storage. The carboxy group is available for activation and coupling with the amino group of another amino acid or peptide fragment. The fluorophenyl group adds a degree of hydrophobicity that can be beneficial for improving peptide solubility in organic solvents or for enhancing membrane permeability in biological systems. These properties are essential for researchers aiming to synthesize peptides with specific conformational or pharmacokinetic characteristics.
NINGBO INNO PHARMCHEM CO.,LTD. is committed to providing researchers with the high-quality chemical tools they need. Understanding the chemical properties of compounds like Fmoc-(S)-3-Amino-4-(2-fluorophenyl)butyric Acid is vital for optimizing synthesis strategies and achieving successful outcomes in drug discovery and peptide research. For inquiries about purchasing this product or for custom synthesis needs, our team of experts is readily available to offer assistance.
Perspectives & Insights
Bio Analyst 88
“This group is a widely adopted orthogonal protecting group in peptide synthesis, particularly in solid-phase peptide synthesis (SPPS).”
Nano Seeker Pro
“The Fmoc group is stable under acidic conditions but is readily cleaved by mild bases, such as piperidine.”
Data Reader 7
“This selective cleavage allows for the stepwise addition of amino acids to a growing peptide chain without affecting other protecting groups or the peptide backbone itself.”