3,4-Difluoro-DL-Phenylalanine is a difluorinated, non-natural phenylalanine derivative in which the aromatic side chain of phenylalanine bears two fluorine substituents at the 3 and 4 positions, with the "DL" designation indicating a racemic mixture of stereoisomers. The molecule contains a free primary amino group and a free carboxylic acid group on the alpha carbon, while the fluorinated benzyl side chain introduces increased electron-withdrawing character and altered hydrophobic/aryl interaction behavior relative to unsubstituted phenylalanine. It is used in peptide and protein structure-property studies, chemical biology probe design, and analytical method development where incorporation of fluorinated amino acid building blocks supports structure-activity comparisons and labeling strategies.
CAT No: CP13003
3,4-Difluoro-DL-Phenylalanine is a difluorinated phenylalanine analog available as a DL (racemic) mixture, featuring two fluorine atoms on the aromatic ring that strongly influence electronic properties and metabolic and analytical behavior compared with unsubstituted phenylalanine. As a non-proteinogenic amino acid building block, it is commonly selected for structure-activity relationship studies and for preparing fluorinated peptide analogs where aryl fluorination provides a handle for physicochemical tuning and mass spectrometric detectability. Researchers use this difluoro-aryl amino acid to introduce a defined aromatic substitution pattern into peptide-based probes and medicinal chemistry intermediates, supporting downstream characterization by LC-MS and related analytical workflows.
1. Peptide Analog Synthesis
3,4-Difluoro-DL-Phenylalanine supports the preparation of fluorinated peptide analogs used in peptide chemistry and chemical biology, where incorporation of a difluoro-substituted aromatic side chain helps probe structure-activity relationships and conformational or interaction trends. Medicinal chemistry groups and custom peptide synthesis providers often select this building block when they need a specific 3,4-difluoro substitution pattern on the phenylalanine side chain for SAR libraries, peptide mimetics, or binding-site mapping studies. The racemic (DL) availability is particularly practical for early-stage analog screening and for generating material sufficient for parallel characterization without committing to a single stereochemical series at the outset.
2. Medicinal Chemistry SAR Building Block
3,4-Difluoro-DL-Phenylalanine is widely used as an amino acid-derived intermediate for medicinal chemistry programs that explore fluorinated aryl motifs to modulate physicochemical properties and improve analytical traceability of analogs. Pharmaceutical and biotech R&D teams incorporate this difluoro-aryl amino acid into peptidomimetic scaffolds and related synthetic intermediates to systematically compare how aromatic fluorination affects potency drivers such as potency-associated binding modes and overall molecular properties. The presence of two ring fluorines also creates a distinctive signature for LC-MS/MS method development and compound confirmation during iterative synthesis campaigns.
3. Chemical Biology Probe and Tagging
3,4-Difluoro-DL-Phenylalanine is used to construct fluorinated peptide probes and labeled analogs where the difluoro-phenylalanine motif serves as a stable structural element for downstream detection and comparative studies. Chemical biology teams often include this building block in probe scaffolds to generate series of analogs that differ in substitution pattern while maintaining a consistent amino acid backbone, enabling more controlled interpretation of assay readouts. Because the aromatic difluoro pattern provides a strong mass spectrometric and structural differentiation point, it is frequently chosen for workflows that rely on LC-MS-based tracking of probe uptake, enrichment, or stability across experimental conditions.
4. Analytical Method Development
3,4-Difluoro-DL-Phenylalanine is frequently employed as a reference material and structural standard in analytical method development for fluorinated amino acid derivatives, including LC-MS/MS workflows used to monitor synthetic intermediates and final fluorinated compounds. Analytical chemistry groups use the compound to verify chromatographic behavior, retention time expectations, and fragmentation patterns for difluoro-aryl amino acid motifs, particularly when developing assays for complex mixtures from peptide or peptidomimetic synthesis. The defined 3,4-difluoro substitution pattern makes it useful for confirming identity and supporting quantitative or semi-quantitative analysis approaches during compound library production.
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