2,3-Difluoro-DL-Phenylalanine is a fluorinated phenylalanine derivative in which two fluorine atoms substitute at the 2- and 3-positions of the aromatic ring, yielding a DL (racemic) mixture at the amino acid stereocenter. The molecule contains a free amino group and a free carboxyl group along with a substituted phenyl side chain bearing the difluoro functionality, which alters electronic properties and can influence hydrophobic and hydrogen-bonding interactions relative to unsubstituted phenylalanine. As a non-natural amino acid, it is used as a chemically defined building block for peptide and amino acid analogue synthesis and for structure-property or structure-activity studies where fluorination enables controlled modulation of side-chain behavior and supports analytical differentiation in biochemical assays.
CAT No: CP12603
2,3-Difluoro-DL-Phenylalanine is a difluorinated phenylalanine analog supplied as a DL mixture, featuring two fluorine atoms on the aromatic ring (2,3-difluoro substitution) that strongly influence electronic properties and aromatic behavior. As a non-natural amino acid building block, it is frequently used in medicinal chemistry and peptide/peptidomimetic development where fluorination provides a practical handle for structure-property studies and for tuning physicochemical characteristics during lead optimization. Its stereochemical DL form supports synthetic workflows that prioritize incorporation into larger frameworks over stereodeconvolution at the building-block stage.
1. Peptidomimetic Building Blocks
2,3-Difluoro-DL-Phenylalanine is used as an amino acid building block for preparing peptidomimetics and fluorinated peptide analogs in hit-to-lead and lead-optimization programs. Researchers in peptide drug discovery and chemical biology incorporate this difluorinated aromatic residue into short bioactive sequences to probe how ring fluorination affects conformational preferences, aromatic interactions, and overall structure-activity relationships. The DL stereochemical form is particularly practical for custom synthesis campaigns when the downstream target sequence is assembled in a way that tolerates racemic incorporation at a single residue position, or when the focus is on generating a library of analogs for comparative evaluation.
2. Medicinal Chemistry SAR Studies
2,3-Difluoro-DL-Phenylalanine supports structure-activity relationship (SAR) studies in medicinal chemistry by providing a defined fluorinated phenylalanine motif that can be introduced into small-molecule scaffolds or peptide-like intermediates. Medicinal chemistry groups use this building block to systematically vary aromatic electronics and steric/electrostatic profiles through difluoro substitution, enabling clearer correlations between chemical structure and measured properties in screening and optimization workflows. The presence of fluorine atoms also makes the residue a convenient design element for NMR-active characterization and for differentiating analogs in analytical workflows during iterative synthesis cycles.
3. Pharmaceutical Intermediate Development
2,3-Difluoro-DL-Phenylalanine is widely used as a specialized intermediate in the synthesis of fluorinated amino acid derivatives and related drug-discovery intermediates. Process and synthetic chemistry teams select this building block when a difluorinated aromatic amino acid fragment is required to access downstream protected forms, activated derivatives, or scaffold-conjugated intermediates used in custom manufacturing and medicinal chemistry supply chains. The stable, well-defined difluoroaromatic substitution pattern helps ensure consistent incorporation of the desired aromatic motif across batches, supporting reproducible intermediate preparation for subsequent coupling, derivatization, or incorporation into larger synthetic targets.
4. Chemical Biology Probe Synthesis
2,3-Difluoro-DL-Phenylalanine is used in chemical biology workflows to construct fluorinated peptide probes and aromatic-tagged analogs for studying binding-site recognition and interaction patterns. Chemical biology groups often choose difluorinated phenylalanine residues to create probes with distinct aromatic electronic character compared with unsubstituted phenylalanine, improving interpretability when comparing analog series in binding and competition experiments. The building-block form enables straightforward incorporation into probe scaffolds during custom synthesis, supporting the generation of structurally matched probe sets where the difluoro substitution is the primary variable.
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