2,5-Difluoro-D-Phenylalanine is a non-natural, fluorinated phenylalanine derivative featuring a benzyl side chain bearing two fluorine atoms at the 2- and 5-positions relative to the benzylic carbon, and it contains both an amino group and a carboxyl group characteristic of amino acids. The molecule is specified as the D stereoisomer and the fluorinated aromatic ring provides distinct electron-withdrawing and steric influences that can alter physicochemical behavior compared with unsubstituted phenylalanine while retaining the α-amino acid backbone for peptide-related chemistry. In research and synthesis, this compound is used as a building block for preparing fluorinated peptides and analogues for structure-property studies, chemical biology labeling strategies, and analytical method development where incorporation of defined fluorine substitution patterns is required.
CAT No: CP12802
2,5-Difluoro-D-Phenylalanine is a D-configured, non-proteinogenic phenylalanine analog bearing two fluorine atoms at the 2- and 5-positions on the aromatic ring. This difluoro substitution provides strong electronic effects and increased metabolic and chemical stability relative to unsubstituted phenylalanine, while retaining an amino acid side chain architecture that is commonly exploited in peptide and peptidomimetic design. Researchers use this fluorinated amino acid building block to probe structure-activity relationships and to introduce controlled aromatic fluorine content into synthetic sequences for downstream analytical and chemical biology workflows.
1. Peptidomimetic Building Blocks
2,5-Difluoro-D-Phenylalanine is used as an amino acid building block for the synthesis of peptidomimetics and fluorinated peptide analogs where aromatic fluorination is leveraged to tune physicochemical properties and structure. Medicinal chemistry groups incorporate this D-amino acid to generate stereochemically defined, non-natural peptide segments for SAR studies, especially when D-configuration is used to modulate conformation and proteolytic stability in synthetic constructs. The difluoro-substituted phenyl ring also offers a chemically informative handle for NMR and mass spectrometry characterization of the resulting sequences, supporting iterative lead optimization in small-molecule and peptide-drug discovery programs.
2. Structure-Activity Relationship Studies
2,5-Difluoro-D-Phenylalanine is frequently selected for SAR and binding-site mapping studies in which systematic changes to aromatic electronics and sterics are required without altering the amino acid backbone framework. By introducing fluorine at the 2- and 5-positions, researchers can evaluate how ring substitution patterns influence conformational preferences, local polarity, and noncovalent interactions within peptide-like ligands. Chemical biology teams use this compound to build analog series that differ specifically at the aromatic residue, enabling clearer interpretation of structure-property relationships in assays that compare fluorinated versus non-fluorinated analogs.
3. Analytical Reference for Fluorinated Residues
2,5-Difluoro-D-Phenylalanine supports analytical method development and reference standard preparation for workflows that quantify or confirm fluorinated amino acid content in synthetic peptides and related materials. Laboratories use the defined difluoro aromatic motif to validate LC-MS/MS transitions and retention behavior for fluorinated residue-containing compounds, and to support targeted characterization of peptide fragments during purification and characterization. The D-stereochemical definition further helps distinguish this analog from other phenylalanine stereoisomers, improving confidence in identity verification for fluorinated building blocks used in research-grade peptide synthesis and intermediate qualification.
4. Chiral Intermediate Development
2,5-Difluoro-D-Phenylalanine is also used as a chiral starting material in the preparation of higher-value fluorinated amino acid derivatives and stereodefined intermediates for downstream synthetic programs. Process development and specialty chemical teams employ this D-amino acid scaffold to access difluoro-aromatic substitution patterns in custom building blocks used for peptide chemistry, medicinal chemistry intermediate libraries, and specialty materials research. The presence of the fluorinated aromatic ring enables consistent incorporation of the difluoro motif across derivative families, supporting reproducible structure control in multi-step development campaigns.
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