2,6-Difluoro-DL-Phenylalanine is a fluorinated phenylalanine derivative in which two fluorine atoms are introduced at the 2- and 6-positions of the benzyl side chain, while the amino acid backbone remains present with an amino group and a carboxyl group. The molecule is supplied as the DL (racemic) stereochemical form and bears a hydrophobic, aromatic side chain whose fluorination alters electronic properties and can modulate intermolecular interactions relative to unsubstituted phenylalanine. It is used in peptide and protein structure-function studies, chemical biology labeling strategies, and analytical method development where incorporation of a difluorinated aromatic residue can provide a defined handle for spectroscopy, mass spectrometry, or structure-activity investigations.
CAT No: CP12903
2,6-Difluoro-DL-Phenylalanine is a difluorinated phenylalanine analog supplied as a DL mixture, combining a phenylalanine backbone with two fluorine atoms at the 2- and 6-positions of the aromatic ring. This substitution pattern introduces distinct electronic effects and steric shielding around the aryl side chain while retaining the amino acid functionality used for downstream synthetic incorporation. As a non-natural aromatic amino acid building block, it is commonly used in medicinal chemistry and peptide/peptidomimetic design workflows where controlled physicochemical and structure-property relationships are required.
1. Peptidomimetic Building Block
2,6-Difluoro-DL-Phenylalanine is used as an aromatic amino acid building block for preparing peptidomimetics and modified peptide analogs in structure-activity relationship (SAR) studies. Researchers incorporate the difluorinated side chain to probe how ring fluorination and ortho substitution influence conformational preferences, local hydrophobicity, and aromatic interactions that often govern binding-site recognition in peptide-like ligands. The DL stereochemical mixture is frequently leveraged at the discovery stage to support rapid analog generation and comparative evaluation across series, especially when subsequent steps allow separation or when stereochemical effects are assessed empirically.
2. Medicinal Chemistry SAR Probes
2,6-Difluoro-DL-Phenylalanine serves as a specialized intermediate for medicinal chemistry programs that require defined aromatic fluorination patterns to tune molecular properties. Fluorine substitution at the 2,6-positions can be used to systematically vary electronic distribution and steric environment around the phenyl ring, supporting studies that correlate chemical structure with potency, selectivity, and physicochemical behavior in lead optimization campaigns. Medicinal chemistry teams typically choose this building block when they want a non-natural phenylalanine variant that can be introduced into larger scaffolds or side-chain-modified analogs without changing the overall amino acid-derived connectivity.
3. Protected Derivative Synthesis
2,6-Difluoro-DL-Phenylalanine is routinely employed as a starting material for preparing amino acid derivatives used in downstream synthesis, including protected forms and activated intermediates for coupling chemistry. Because the compound contains the amino acid motif with a difluorinated aromatic side chain, it is a practical feedstock for assembling larger molecules that incorporate the 2,6-difluorophenylalanine motif while controlling functional-group reactivity during multistep synthesis. Pharmaceutical intermediate development groups and custom synthesis providers use it to build libraries of analogs where the difluorinated aryl group must be preserved through protection, activation, and coupling steps.
4. Chemical Biology Ligand Analogues
2,6-Difluoro-DL-Phenylalanine is also used to generate ligand analogues for chemical biology and protein-interaction studies, particularly when aromatic fluorination is introduced to modulate binding interactions in peptide-like recognition elements. In research settings, the difluorinated phenylalanine motif can be incorporated into synthetic ligands to create structure-defined probes for evaluating how aromatic ring substitution affects recognition by enzymes, receptors, or binding domains. Teams often select this building block when they want a non-natural amino acid variant that maintains the amino acid-derived geometry while providing a chemically distinct aryl environment for comparative binding and competition experiments.
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