2,5-Difluoro-L-Phenylalanine is a fluorinated, proteinogenic amino acid analogue classified as an L-phenylalanine derivative in which two fluorine atoms are substituted on the phenyl ring at the 2- and 5-positions. The molecule contains both an amino group and a carboxyl group characteristic of amino acids, while the difluoro-substituted aromatic side chain modulates electronic density and can influence hydrophobic and hydrogen-bonding interactions through the electronegative fluorine substituents. As a defined stereochemical amino acid building block, it is used in peptide synthesis and structure-activity or structure-property studies to introduce fluorinated aromatic residues for probing conformational effects, binding interactions, and analytical detectability in chemical biology and biomaterials research.
CAT No: CP12801
2,5-Difluoro-L-Phenylalanine is a fluorinated L-phenylalanine analog in which two fluorine atoms are installed on the aromatic ring (positions 2 and 5). As a non-natural aromatic amino acid building block, it is widely used to introduce controlled steric and electronic effects into peptides and peptidomimetics, while also providing a chemically distinctive handle for analytical workflows where fluorine-containing motifs are advantageous. Researchers typically select this L-amino acid for structure-property studies, medicinal chemistry optimization, and the preparation of defined fluorinated peptide intermediates for downstream biological or biophysical evaluation.
1. Peptide Building Block Use
2,5-Difluoro-L-Phenylalanine is used as a defined amino acid building block for incorporating a fluorinated phenylalanine residue into peptides via standard peptide synthesis workflows. Medicinal chemistry groups and peptide researchers employ it to probe how aromatic fluorination alters local conformational preferences, side-chain electronics, and physicochemical behavior within peptide sequences. Because the fluorines are embedded directly in the side-chain ring, the residue can be introduced at specific positions to support structure-activity relationship (SAR) and sequence optimization campaigns, generating fluorinated analogs suitable for comparative studies in peptide libraries and custom peptide synthesis.
2. Medicinal Chemistry SAR Probes
2,5-Difluoro-L-Phenylalanine supports medicinal chemistry programs that require aromatic fluorine substitution as a rational probe for aromatic ring effects. In practice, medicinal chemists use this building block to prepare peptidomimetic fragments and fluorinated analog series where the ring substitution pattern is kept constant while other structural elements vary, enabling focused interpretation of how fluorination changes properties such as lipophilicity balance, hydrogen-bonding patterns at the aromatic periphery, and metabolically relevant chemical environment. The residue's defined stereochemistry and aromatic substitution pattern make it a practical choice for generating consistent analogs for SAR documentation and iterative lead optimization.
3. Fluorine-Enabled Analytical Standards
2,5-Difluoro-L-Phenylalanine is frequently selected for analytical method development and reference material preparation in workflows that benefit from fluorine-containing targets. Analytical chemistry and chemical biology teams use fluorinated amino acid standards to support LC-MS/MS quantification of peptide or small-molecule derivatives containing the difluorophenylalanine motif, and to facilitate unambiguous identification in complex mixtures where fluorine-bearing fragments provide distinctive mass spectrometric signatures. This makes the compound useful for preparing calibration components, internal reference materials for method validation, and defined substrates or intermediates used to verify downstream labeling or coupling outcomes in fluorinated series.
4. Pharmaceutical Intermediate Development
2,5-Difluoro-L-Phenylalanine is also used as a pharmaceutical intermediate building block for producing fluorinated peptide fragments and related synthetic intermediates that feed into larger medicinal chemistry syntheses. Industrial and contract research chemistry teams incorporate this residue into protected or activated intermediate sequences to enable downstream assembly of fluorinated compounds with controlled aromatic substitution. The product's stable, non-natural amino acid identity helps ensure that the difluorophenyl motif is introduced reproducibly and traceably across batch-to-batch intermediate preparation, supporting scalable synthesis of fluorinated analog sets for research-stage development.
4. TMEM16F and dynamins control expansive plasma membrane reservoirs
5. Autoinhibition and phosphorylation-induced activation of phospholipase C-γ isozymes
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