3,5-Difluoro-DL-Phenylalanine is a fluorinated, non-natural phenylalanine derivative in which the phenyl side chain bears two fluorine atoms at the 3 and 5 positions. The molecule contains both an amino group and a carboxyl group on the α-carbon framework and is supplied as the DL stereochemical mixture, with the side chain retaining the aromatic functionality while the fluorine substituents modulate electronic properties and hydrogen-bonding behavior. It is used in peptide and protein structure-function studies and in analytical or chemical biology workflows where fluorinated amino acids provide spectroscopic and structural contrast for incorporation into synthetic peptide materials and related labeling or structure-activity investigations.
CAT No: CP13103
3,5-Difluoro-DL-Phenylalanine is a difluorinated phenylalanine analog provided as a DL mixture, featuring two fluorine atoms on the aromatic ring that strongly influence electronics, lipophilicity, and metabolic stability relative to unsubstituted phenylalanine. As a non-natural amino acid building block, it is widely used in peptide and peptidomimetic design where aryl fluorination is leveraged to tune physicochemical properties and probe structure-property relationships. Its free amino acid functionality makes it a practical intermediate for downstream coupling workflows in medicinal chemistry and materials-oriented organic synthesis.
1. Peptidomimetic Building Blocks
3,5-Difluoro-DL-Phenylalanine is used as an amino acid building block for incorporating difluorinated aryl side chains into peptide mimetics and constrained analogs during lead optimization. Medicinal chemistry groups and custom peptide manufacturers commonly select this scaffold when they want to systematically vary aromatic electronics and steric/electronic effects while retaining an amino acid-derived backbone for synthetic accessibility. The difluoro-substituted phenyl ring provides a chemically robust handle that can be carried through iterative structure-activity relationship (SAR) synthesis, enabling comparative studies against non-fluorinated or mono-fluorinated analogs. Researchers also use it when preparing defined analog panels for binding-site mapping by competition assays or for profiling how aryl fluorination changes conformational preferences and noncovalent interactions in model systems.
2. Medicinal Chemistry SAR Studies
3,5-Difluoro-DL-Phenylalanine supports medicinal chemistry programs that require rapid access to aryl-fluorinated amino acid motifs for SAR and analog diversification. In practice, it is employed to generate series of peptidic or peptidomimetic intermediates where the fluorination pattern is used as a controlled variable to assess how changes in aromatic substitution affect potency-related readouts, selectivity trends, or metabolic behavior in preclinical discovery workflows. Because the material is supplied as a DL mixture, it is frequently used for early-stage library synthesis and feasibility studies where stereochemical purity is not the primary driver of the experimental design. The aromatic difluoro substitution also makes it a useful reference component when correlating physicochemical property changes with downstream assay outcomes in chemical biology campaigns.
3. Pharmaceutical Intermediate Synthesis
3,5-Difluoro-DL-Phenylalanine is also used as a pharmaceutical intermediate for preparing fluorinated amino acid derivatives and downstream coupling partners used in specialty chemical manufacturing. Process and development chemists incorporate this building block into routes that generate protected amino acid derivatives, activated esters, or other coupling-ready forms for assembling larger fragments in medicinal chemistry synthesis. The presence of two fluorine atoms on the aromatic ring helps create a consistent, well-defined substituent pattern across batches, which is valuable for reproducible intermediate profiling and analytical method development. This makes the compound a practical choice for teams building fluorinated analog libraries, where maintaining the exact aryl substitution pattern is essential for traceable structure-composition relationships.
4. Analytical Reference Standards
3,5-Difluoro-DL-Phenylalanine is frequently used as a structural reference standard in analytical workflows that monitor fluorinated amino acid incorporation or verify the identity of fluorinated intermediates in synthesis and purification. Analytical chemistry laboratories use it to support LC-MS method development, retention-time and fragmentation pattern confirmation, and calibration/qualification strategies when difluorinated phenylalanine motifs are expected in complex reaction mixtures or final peptide/peptidomimetic products. The distinct mass signature imparted by the two fluorine atoms enables clear discrimination from non-fluorinated phenylalanine analogs, improving confidence during method optimization and troubleshooting. Researchers also use it when validating analytical panels for fluorinated building blocks used in SAR studies, ensuring that the targeted aryl substitution pattern is correctly represented throughout the development workflow.
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