2,6-Difluoro-D-Phenylalanine is a non-natural, aromatic amino acid derivative in which a D-configured phenylalanine backbone bears two fluorine atoms at the 2- and 6-positions of the benzyl side chain. The molecule contains a free amino group and a free carboxyl group, with the fluorinated aromatic ring providing increased electron-withdrawing character and altered hydrophobic and steric features relative to unsubstituted phenylalanine. As a fluorinated stereodefined amino acid, it is used in peptide and protein structure-activity studies, chemical biology labeling strategies, and NMR- or mass-spectrometry-based analytical workflows where fluorine substitution and D-configuration are used to probe incorporation, conformation, and interaction effects.
CAT No: CP12902
2,6-Difluoro-D-Phenylalanine is a D-configured, non-proteinogenic fluorinated phenylalanine analog featuring two fluorine atoms on the aromatic ring (2,6-difluoro substitution). This substitution pattern provides distinctive electronic and steric properties relative to phenylalanine, making the compound a valuable chiral amino acid building block for structure-activity relationship studies and for the preparation of fluorinated peptide and peptidomimetic motifs. Researchers typically use this reagent when they need a defined stereochemical handle and a metabolically and analytically "taggable" aryl fluorine environment for downstream synthesis and characterization workflows.
1. Peptidomimetic Building Blocks
2,6-Difluoro-D-Phenylalanine is used as a stereochemically defined amino acid building block for incorporating D-aryl motifs into peptidomimetic scaffolds and fluorinated peptide analogs. Medicinal chemistry groups and custom peptide synthesis providers select the 2,6-difluoro aryl pattern to tune local sterics and electronics around the side chain, supporting SAR campaigns where aryl substitution is used to modulate conformational preferences and intermolecular interactions. Because the reagent is a discrete, single stereoisomer building block, it is commonly employed in workflows that require consistent residue identity across libraries, including solution-phase and solid-phase assembly of modified peptide segments.
2. Protein Engineering Probes
2,6-Difluoro-D-Phenylalanine supports protein and enzyme research efforts that rely on non-natural amino acid incorporation strategies to interrogate structure-function relationships. Chemical biology teams often use fluorinated aryl amino acid analogs as residue-specific probes because the fluorine atoms can serve as informative reporters in NMR-based characterization and as chemically distinct substituents for tracking incorporation in engineered constructs. The D-configuration further enables studies where stereochemistry at a single residue is expected to alter local backbone/side-chain geometry, helping researchers evaluate how non-native stereochemical constraints influence protein conformation, stability, or interaction surfaces in controlled experimental systems.
3. Medicinal Chemistry SAR Studies
2,6-Difluoro-D-Phenylalanine is frequently selected for medicinal chemistry programs developing fluorinated peptidomimetics and small-molecule/peptide hybrids where aryl fluorination is used to refine physicochemical properties and binding-site complementarity. SAR scientists value the 2,6-difluoro substitution because it provides a compact, strongly electron-withdrawing pattern that can influence aromatic ring interactions and hydrogen-bonding networks in binding pockets. The reagent's defined D stereochemistry also helps teams attribute observed changes in activity or selectivity trends to stereochemical residue identity rather than to mixture effects, which is particularly important when generating matched analog series for lead optimization and mechanistic follow-up.
4. Analytical Reference Standards
2,6-Difluoro-D-Phenylalanine is used to prepare analytical reference materials and method-development standards for LC-MS workflows involving fluorinated amino acid residues and peptide fragments. Analytical chemistry groups and proteomics/peptidomics researchers often require well-defined, non-natural amino acid standards to confirm retention-time behavior and mass spectral features for fluorinated building blocks and their incorporation products. The presence of two fluorine atoms improves the diagnostic value of the aryl moiety in fragmentation and mass-based identification, making this reagent useful when validating sample processing, monitoring derivatization steps, or establishing quantitative calibration strategies for fluorinated peptide analog analyses.
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5. SERS spectrum of the peptide thymosin‐β4 obtained with Ag nanorod substrate
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