2,6-Difluoro-L-Phenylalanine is a fluorinated, proteinogenic amino acid derivative in which the phenylalanine side chain bears two fluorine substituents at the 2- and 6-positions of the aromatic ring while retaining the L-amino acid backbone. The molecule contains a free amino group and a carboxyl group and features a substituted benzyl side chain whose difluoro substitution modulates aromatic electronics and steric environment compared with unsubstituted phenylalanine. It is used in peptide and protein structure-function studies, chemical biology labeling strategies, and analytical method development where controlled incorporation of a fluorinated phenylalanine analogue helps probe local environment effects, conformational preferences, or spectroscopic/LC-MS behavior.
CAT No: CP12901
2,6-Difluoro-L-Phenylalanine is a fluorinated phenylalanine analog in the L-configuration, bearing two fluorine atoms on the aromatic ring at the 2- and 6-positions. This substitution increases aromatic electronic and steric differentiation relative to standard phenylalanine while retaining the amino acid backbone required for peptide incorporation and downstream derivatization. In research settings, it is used as a defined aromatic building block for structure-property studies, peptide and peptidomimetic development, and analytical method support where fluorinated aromatic residues provide distinct mass and physicochemical behavior.
1. Peptide Building Block Applications
2,6-Difluoro-L-Phenylalanine is used as an amino acid building block for custom peptide synthesis and peptidomimetic design, particularly when researchers want a metabolically and chemically defined aromatic residue with altered steric and electronic characteristics. Medicinal chemistry groups incorporate this fluorinated phenylalanine analog into short peptides and SAR (structure-activity relationship) libraries to probe how ring substitution patterns influence conformation, local interactions, and overall peptide behavior. Because the compound is an L-amino acid, it is commonly selected when stereodefined incorporation into peptide sequences is required for consistent structure-property comparisons.
2. Protein And Enzyme Studies
2,6-Difluoro-L-Phenylalanine supports chemical biology and protein science workflows that rely on site-specific or residue-level perturbations of aromatic side chains. Researchers use fluorinated phenylalanine analogs to interrogate how modified aromatic environments affect binding interfaces, substrate recognition, or catalytic-site microenvironments in model peptides and protein fragments. The 2,6-difluoro substitution pattern is especially useful for experiments where steric shielding around the aromatic ring and distinctive fluorine-driven properties are expected to change interaction profiles, while still maintaining an amino acid side chain that can be positioned within peptide constructs for controlled comparisons.
3. Fluorinated SAR Intermediate Development
2,6-Difluoro-L-Phenylalanine is frequently employed in medicinal chemistry and pharmaceutical intermediate development as a defined fluorinated aromatic amino acid precursor for building fluorinated scaffolds. Process and research teams use it to prepare peptide-like intermediates and aromatic fragments where the presence of two ring fluorines provides a handle for tuning lipophilicity, electronic character, and metabolic stability hypotheses during lead optimization. Its rigid, stereodefined amino acid framework makes it a practical starting point for downstream functionalization strategies that preserve the substituted aromatic motif through multistep synthesis toward fluorinated bioactive candidates or advanced research standards.
4. Quantitative LC-MS Standards
2,6-Difluoro-L-Phenylalanine is used as a reference material and analytical standard in workflows that require a fluorinated amino acid with a distinct mass signature. Analytical chemistry and metabolomics groups employ it to support LC-MS method development, calibration, and identification of fluorinated amino acid-containing peptides or labeled/derivatized derivatives generated in peptide chemistry studies. The two fluorine atoms provide a predictable mass shift and improved chromatographic/ionization distinctness versus non-fluorinated phenylalanine, which helps researchers distinguish target-containing species during method validation and comparative quantitation experiments.
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