2,4,5-Trifluoro-D-Phenylalanine is a non-natural, fluorinated phenylalanine derivative in which three fluorine atoms are substituted at the 2, 4, and 5 positions of the phenyl ring, with the amino acid skeleton specified as the D stereochemical form. The molecule contains a free amino group and a free carboxyl group, while the electron-withdrawing fluorines modulate the aromatic side-chain polarity and can influence conformational preferences and intermolecular interactions relevant to peptide and protein analogs. It is used as a substrate-like building block for peptide synthesis and as a chemically defined aromatic fluorinated amino acid for structure-activity studies, labeling strategies, and analytical method development where fluorination provides distinct spectroscopic and physicochemical behavior.
CAT No: CP16902
2,4,5-Trifluoro-D-Phenylalanine is a D-configured fluorinated phenylalanine analog in which three ring fluorines strongly influence aromatic electronics and steric profile. This non-proteinogenic amino acid building block is commonly used in peptide and peptidomimetic research where fluorinated side chains help tune physicochemical properties and provide a distinct handle for analytical differentiation. Its defined stereochemistry supports incorporation into synthetic sequences and structure-activity studies that require stereochemical control.
1. Peptide Building Block Use
2,4,5-Trifluoro-D-Phenylalanine is used by peptide chemistry groups to introduce a D-amino acid residue bearing a highly fluorinated aromatic side chain into custom peptides, peptidomimetics, and SAR libraries. The D-configuration supports stereochemical design in sequence contexts where resistance to proteolysis and backbone stereochemical effects are important for downstream evaluation. Researchers also value the trifluorinated phenyl ring as a chemically distinctive motif that can improve interpretability in LC-MS workflows and help separate analogs that differ only in aromatic substitution patterns.
2. Medicinal Chemistry SAR Probing
2,4,5-Trifluoro-D-Phenylalanine is applied in medicinal chemistry programs developing fluorinated amino acid analogs for structure-activity relationship studies and conformational/electronic tuning. Medicinal chemistry and chemical biology teams incorporate this residue into lead optimization scaffolds to systematically vary aromatic substitution while maintaining a consistent amino acid stereochemical framework. The dense fluorination pattern provides a strong electronic perturbation relative to unsubstituted or monofluorinated phenylalanine analogs, supporting rational comparison across closely related analog series during hit-to-lead refinement.
3. Chemical Biology Label Differentiation
2,4,5-Trifluoro-D-Phenylalanine is used in chemical biology and analytical method development where fluorinated amino acid reporters improve mass spectrometric discrimination between structurally similar peptide standards. Researchers preparing reference peptides for quantitation, profiling, or method validation often select this building block to generate a clear mass signature and to reduce ambiguity when multiple aromatic substitutions are present in a sample set. The D-stereochemistry further supports the construction of stereochemically defined standards that match synthetic targets or control peptides used in comparative studies.
4. Chiral Intermediate Development
2,4,5-Trifluoro-D-Phenylalanine is also used as a chiral amino acid intermediate for downstream synthesis of fluorinated building blocks and specialty intermediates in industrial and research settings. Process development teams and fine-chemical manufacturers leverage its defined D-configuration and trifluorinated aromatic functionality to access fluorinated derivatives used in materials research, specialty reagents, and fluorinated small-molecule scaffolds. In these workflows, the compound's stereochemical integrity and robust aromatic fluorination pattern help maintain consistency across batch-to-batch intermediate production for subsequent derivatization steps.
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