2,4-Difluoro-L-Phenylalanine is a fluorinated, proteinogenic amino acid analogue in which the phenyl side chain of L-phenylalanine bears two fluorine substituents at the 2- and 4-positions. The molecule contains both an amino functional group and a carboxyl functional group characteristic of amino acids, and it retains the L-stereochemical configuration indicated in the name while presenting a difluoro-substituted aromatic ring that can modulate hydrophobicity and electronic properties. As a non-native aromatic amino acid building block, it is used in peptide and protein engineering workflows and in chemical biology or analytical studies where incorporation of a fluorinated residue supports structure-activity comparisons, labeling strategies, or spectroscopic and mass-based characterization.
CAT No: CP12701
2,4-Difluoro-L-Phenylalanine is a fluorinated, proteinogenic amino acid analog featuring two fluorine atoms on the phenyl ring and the L-configuration at the alpha carbon. This side-chain substitution provides distinct steric and electronic properties compared with phenylalanine, making it a useful building block for peptide and peptidomimetic design where aromatic fluorination can modulate physicochemical behavior and enable structure-property studies. In synthetic and medicinal chemistry workflows, it is commonly selected to introduce a defined difluoroaryl motif at a specific position within larger molecules.
1. Peptide Building Block
2,4-Difluoro-L-Phenylalanine is used as a defined aromatic amino acid building block for the synthesis of peptides and peptide-like scaffolds in both academic and industrial research settings. Researchers incorporate the difluoroaryl side chain at specific sequence positions to probe how ring fluorination influences conformation, local polarity, and overall molecular properties in structure-activity relationship (SAR) studies. The L stereochemistry supports consistent behavior in peptide assembly workflows, while the difluoro substitution provides a chemically stable aromatic handle that can be retained through downstream purification and analytical characterization of peptide intermediates and final products.
2. Medicinal Chemistry SAR Studies
2,4-Difluoro-L-Phenylalanine supports medicinal chemistry programs focused on systematic SAR exploration of fluorinated aromatic motifs in bioactive lead series and peptidomimetic candidates. Medicinal chemists use this amino acid analog to introduce a controlled 2,4-difluorophenyl element into larger fragments, enabling direct comparison against non-fluorinated or mono-fluorinated analogs while keeping the backbone and substitution pattern well-defined. The presence of two fluorine atoms also makes the compound a practical choice for NMR-active labeling of aromatic environments within synthesized intermediates, supporting structure verification and conformational analysis during lead optimization.
3. Protein Engineering Probes
2,4-Difluoro-L-Phenylalanine is applied in chemical biology and protein science workflows that require site-specific incorporation of fluorinated aromatic residues for structural and functional interrogation. Teams performing protein engineering or protein labeling studies use this amino acid analog to create defined perturbations at aromatic positions, supporting experiments that correlate residue-level changes with measurable outcomes such as altered chemical reactivity patterns or spectroscopic signatures. The difluoro substitution is particularly valuable when researchers want a residue that differs electronically from phenylalanine while remaining compatible with peptide/protein fragment synthesis and subsequent characterization.
4. Analytical Reference Standards
2,4-Difluoro-L-Phenylalanine is also used to prepare analytical reference materials for method development and validation in LC-MS and related workflows involving fluorinated amino acid-containing peptides and intermediates. Analytical teams incorporate the compound as a structurally matched standard to confirm retention behavior, ionization response, and fragmentation patterns for difluoroaryl-containing analytes. Because the substitution pattern is unambiguous and the L stereochemistry is defined, it is well-suited for supporting quantitative or qualitative assessments of fluorinated species formed during synthesis, purification, or stability studies of larger labeled molecules.
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