2,5-Difluoro-DL-Phenylalanine is a fluorinated, non-proteinogenic amino acid derivative featuring the phenylalanine backbone with two fluorine substituents at the 2- and 5-positions of the aromatic ring and a DL stereochemical designation indicating a racemic mixture. The molecule contains a free amino group and a free carboxyl group alongside a substituted benzyl side chain whose difluoro substitution alters aromatic electronics and hydrogen-bonding behavior relative to unsubstituted phenylalanine. In peptide chemistry and chemical biology, this difluorinated analogue is used as a defined building block for structure-activity studies, incorporation into synthetic peptides, and analytical method development where fluorinated aromatic residues provide spectroscopic and mass-spec distinguishability.
CAT No: CP12803
2,5-Difluoro-DL-Phenylalanine is a difluorinated phenylalanine analog supplied as a racemic mixture (DL), featuring two fluorine atoms on the aromatic ring that strongly influence electronic properties and metabolic stability trends in downstream molecules. As an amino acid building block, it is commonly used in medicinal chemistry and peptide/peptidomimetic design workflows where aromatic fluorination is leveraged to probe structure-activity relationships, alter physicochemical behavior, and tune interactions in target-binding scaffolds. The free amino acid form provides the primary amine and carboxylic acid functionality needed for incorporation into protected intermediate sequences and subsequent coupling strategies.
1. Peptidomimetic Building Blocks
2,5-Difluoro-DL-Phenylalanine is used as an aromatic fluorinated amino acid building block for constructing peptidomimetics and fluorinated analogs in custom peptide synthesis and medicinal chemistry programs. Researchers incorporate the difluoro-phenylalanine residue into short bioactive peptide fragments or constrained mimetics to evaluate how ring fluorination affects conformational preferences, hydrophobic/aromatic character, and hydrogen-bonding patterns at the binding interface. The DL stereochemical form is particularly useful for generating libraries where stereochemical effects are screened empirically, and the fluorinated aromatic ring provides a chemically robust handle for comparative SAR studies against non-fluorinated phenylalanine controls.
2. Medicinal Chemistry SAR Probes
2,5-Difluoro-DL-Phenylalanine supports structure-activity relationship (SAR) investigations in small-molecule and peptide-like drug discovery by enabling systematic variation of aromatic substitution patterns. Medicinal chemists use difluorinated phenylalanine derivatives to create analog series that probe how electron-withdrawing fluorine atoms modulate binding interactions and overall molecular properties such as polarity and lipophilicity balance. Because the fluorines are directly embedded on the aromatic ring, this building block is frequently selected when the goal is to introduce a defined electronic perturbation while maintaining the amino acid-derived scaffold geometry used in many pharmacophore designs.
3. Pharmaceutical Intermediate Development
2,5-Difluoro-DL-Phenylalanine is also employed as a pharmaceutical intermediate for manufacturing fluorinated amino acid derivatives and downstream coupling partners used in development chemistry. Process and synthesis teams use this building block to prepare protected amino acid forms and activated derivatives that feed into stepwise assembly of fluorinated intermediates for lead optimization. The presence of the difluorinated aromatic ring makes it a practical precursor for generating consistently substituted scaffolds at scale, supporting reproducible analog production for medicinal chemistry campaigns and analytical reference material generation during development.
4. Analytical Reference Standards
2,5-Difluoro-DL-Phenylalanine is used in analytical method development and reference standard preparation for studies that track fluorinated amino acid incorporation or monitor fluorinated metabolite/fragment formation in chemical biology and metabolic research workflows. Analytical chemists and method developers use the racemic difluoro-phenylalanine scaffold as a defined mass-tagged chemical entity for LC-MS based quantitation, calibration, and identity confirmation of fluorinated species in complex mixtures. The chemically distinctive difluoro aromatic motif helps distinguish it from non-fluorinated amino acid backgrounds, making it a practical component for validating analytical procedures that involve fluorinated building blocks and their downstream derivatives.
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