2,4,5-Trifluoro-DL-Phenylalanine is a non-natural phenylalanine derivative in which three fluorine atoms substitute the aromatic ring at the 2-, 4-, and 5-positions, yielding a DL stereochemical mixture at the amino acid center. The molecule contains a free amino group and a free carboxyl group attached to the substituted benzyl side chain, with the fluorinated aryl functionality providing increased electron-withdrawing character and altered hydrophobic and steric properties relative to unmodified phenylalanine. It is used in peptide and structure-activity studies as a fluorinated amino acid building block to probe how aromatic fluorination affects conformational preferences, labeling or spectroscopic behavior, and the properties of peptide analogues prepared by chemical synthesis.
CAT No: CP16903
2,4,5-Trifluoro-DL-Phenylalanine is a fluorinated phenylalanine analog available as a DL mixture, bearing three fluorine atoms on the aromatic ring that strongly influence electronic properties and metabolic stability trends in downstream systems. As an amino-acid building block, it is used in medicinal chemistry and peptide/peptidomimetic research where aromatic fluorination is leveraged to tune physicochemical behavior and probe structure-property relationships. Its amino acid functionality enables incorporation into synthetic sequences and analytical reference workflows, while the fluorinated side chain provides a distinctive handle for NMR and mass spectrometric characterization.
1. Peptidomimetic Building Blocks
2,4,5-Trifluoro-DL-Phenylalanine is used as a fluorinated amino-acid building block for the preparation of peptidomimetics and modified peptide-like scaffolds in structure-activity relationship (SAR) studies. Medicinal chemistry groups incorporate this aromatic trifluorinated residue to study how ring fluorination affects conformation, lipophilicity, and overall molecular recognition patterns, particularly in series where phenylalanine analogs are systematically varied. The DL stereochemical form is commonly selected for exploratory synthesis and library generation when relative stereochemistry is not the primary optimization variable, enabling efficient access to analog sets for downstream biological and biophysical evaluation. In synthesis planning, the molecule's protected amino acid compatibility is typically handled via standard amino-acid derivative workflows, allowing the trifluorinated aromatic ring to be retained through assembly and purification.
2. Structure-Property SAR Studies
2,4,5-Trifluoro-DL-Phenylalanine supports medicinal chemistry programs focused on quantifying the impact of aromatic fluorination on drug-like properties and binding-site interactions. Researchers use this residue in analog design to create controlled variations relative to non-fluorinated phenylalanine, enabling direct comparisons across series while keeping the backbone framework consistent. The three fluorine substituents provide a strong electronic perturbation and a characteristic spectroscopic signature, which helps teams confirm incorporation and monitor structural integrity during iterative synthesis. Because the compound is supplied as a DL mixture, it is frequently used for early-stage SAR screening and for generating material for computational model training or experimental property mapping where stereochemical resolution is not yet required.
3. NMR And LC-MS Characterization
2,4,5-Trifluoro-DL-Phenylalanine is widely used as a fluorinated reference component for analytical method development and compound identification in LC-MS and NMR workflows. The trifluorinated aromatic ring yields distinctive 19F NMR responses and contributes to predictable mass spectral patterns, making it valuable for confirming the presence of the fluorinated residue in complex reaction mixtures, peptide fragments, and final analogs. Analytical chemists and process development scientists also use it to benchmark chromatographic behavior and to validate transitions or fragmentation patterns for quantitative assays that track fluorinated intermediates. In practice, the DL form is often acceptable for analytical confirmation when the primary requirement is structural verification of the trifluorinated motif rather than stereospecific quantitation.
4. Pharmaceutical Intermediate Development
2,4,5-Trifluoro-DL-Phenylalanine is employed as a key intermediate building block in the preparation of fluorinated amino-acid derivatives used for downstream synthesis of medicinal chemistry candidates. Process and synthetic development teams rely on this scaffold to introduce a trifluorinated phenylalanine element into larger frameworks, including constrained amino-acid analogs, side-chain-modified intermediates, and specialized coupling partners for custom peptide or peptidomimetic assembly. The presence of the amino acid functional group ensures it can be converted into derivative forms compatible with standard intermediate-handling workflows, while the trifluorinated aromatic ring remains a stable structural feature through multi-step sequences. This makes the material practical for iterative route development where consistent incorporation of the fluorinated residue is required across multiple analogs.
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