3,5-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 3 and 5 positions. The molecule contains a free amino group and a carboxyl group characteristic of amino acids, with the aromatic ring modified to introduce increased electron-withdrawing character and altered hydrophobic and packing properties relative to the unsubstituted phenylalanine side chain. It is used in peptide and protein structure-activity studies, chemical biology labeling approaches, and analytical method development where fluorinated amino acid incorporation or detection can provide a spectroscopic or structural handle.
CAT No: CP13101
3,5-Difluoro-L-Phenylalanine is a fluorinated L-phenylalanine analog in which two fluorine atoms are installed on the aromatic ring, creating a distinctive electronic and steric environment while retaining the standard amino acid backbone used in peptide chemistry. This non-proteinogenic aromatic amino acid is frequently selected in structure-activity relationship studies and synthetic peptide design to probe how aryl fluorination influences conformation, hydrophobicity, and physicochemical behavior. Researchers also use it as a defined building block to introduce a metabolically and analytically tractable fluorinated motif into larger molecules for downstream characterization.
1. Peptide Building Block
3,5-Difluoro-L-Phenylalanine is used by peptide chemists and custom peptide synthesis groups to incorporate a difluorinated aromatic residue into linear peptides and peptidomimetics. The fluorinated side chain provides a chemically stable handle for later analytical verification and for tuning properties such as aromatic electronics and lipophilicity without changing the amino acid stereochemical identity of the backbone. This makes the residue a practical choice when developing peptide libraries, SAR panels, or mechanistic peptide probes where the aromatic substitution pattern must be controlled precisely.
2. Medicinal Chemistry SAR Studies
3,5-Difluoro-L-Phenylalanine is commonly employed in medicinal chemistry workflows that evaluate how ring fluorination affects binding-site interactions and overall molecular behavior of peptidic or amino acid-derived scaffolds. Medicinal chemistry teams use this defined fluorinated amino acid to generate analog series with systematic variation of aromatic substitution, supporting structure-activity relationship campaigns and conformational or electronic effect studies. Because the product contains a well-defined difluorinated motif, it also supports unambiguous compound identity confirmation during synthesis-to-analytics transitions.
3. Fluorinated Intermediate Development
3,5-Difluoro-L-Phenylalanine serves as a practical intermediate for the preparation of fluorinated amino acid derivatives and downstream building blocks used in specialty chemical and pharmaceutical intermediate development. Process and R&D chemists leverage the intact amino acid functionality to access protected forms, activated derivatives, or incorporation-ready fragments that retain the difluorinated phenyl motif through subsequent synthetic steps. This is particularly useful when the target molecule requires a controlled fluorinated aromatic unit for property tuning, analytical traceability, or late-stage diversification.
4. LC-MS and NMR Reference Material
3,5-Difluoro-L-Phenylalanine is frequently used as an analytical reference for method development and compound identification in LC-MS workflows involving fluorinated aromatic amino acids and peptide fragments. Analytical groups and method developers value the distinct fluorination pattern for chromatographic and mass spectral differentiation from non-fluorinated phenylalanine derivatives. In structure confirmation workflows, the difluorinated aromatic ring also provides characteristic NMR observables that support verification of substitution patterns in intermediate and final synthetic materials.
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