Boc-2,5-Difluoro-D-Phenylalanine is a protected, non-natural amino acid derivative featuring a D-configuration at the alpha carbon and a phenylalanine backbone bearing two fluorine substituents at the 2- and 5-positions of the aromatic ring. The molecule contains a Boc-protected amino group and a free carboxyl group, and the fluorinated aromatic side chain provides distinct electronic and steric characteristics that can influence peptide microenvironments and conformational preferences. In peptide chemistry and chemical biology, this Boc-protected difluorinated amino acid is used as a building block for stepwise assembly of modified peptides and for structure-activity or labeling studies where aryl fluorination is used to tune physicochemical behavior.
CAT No: CP12805
Boc-2,5-Difluoro-D-Phenylalanine is a D-configured, non-proteinogenic phenylalanine analog bearing fluorine substituents at the 2- and 5-positions of the aromatic ring and a Boc-protecting group on the amino functionality. This protected amino acid building block is commonly used in peptide and peptidomimetic synthesis workflows where aromatic fluorination and defined stereochemistry are leveraged to tune physicochemical properties and support structure-activity relationship (SAR) studies. Its protected form makes it directly compatible with standard amino acid coupling strategies used to assemble modified peptide segments.
1. Peptidomimetic SAR Building
Boc-2,5-Difluoro-D-Phenylalanine is used by medicinal chemistry teams to construct peptidomimetic analogs for SAR campaigns, where aromatic difluorination and D-configuration help probe how side-chain electronics and steric presentation influence binding-site interactions and overall molecule behavior. In practice, this building block is incorporated into short peptide-like sequences and constrained analogs to generate structure-defined series for downstream profiling in chemical biology assays and lead optimization programs. The Boc protection supports reliable segment assembly during custom peptide synthesis, enabling consistent incorporation of this fluorinated residue into otherwise conventional peptide backbones.
2. Modified Peptide Synthesis
Boc-2,5-Difluoro-D-Phenylalanine serves as a protected amino acid building block for both solution-phase and solid-phase workflows that require non-natural aromatic substitutions. Peptide synthesis groups use it to introduce a fluorinated D-phenylalanine residue at a defined position, supporting the preparation of modified peptides used for mechanistic chemical biology studies, binding assays, and structure-focused characterization. The presence of the Boc group on the amino terminus supports routine coupling chemistry in peptide assembly, while the difluorinated aromatic ring provides a chemically stable handle for generating analogs with distinct NMR and mass spectrometric signatures during purification and analytical verification.
3. Fluorinated Residue Labeling
Boc-2,5-Difluoro-D-Phenylalanine is frequently selected by analytical chemistry and chemical biology laboratories to prepare fluorinated peptide standards and reference materials where the 2,5-difluoro motif improves traceability by LC-MS and 19F NMR-based workflows. Researchers incorporate this residue into peptide sequences designed as internal or external standards for method development, instrument qualification, and comparative quantitation across analog series. The protected, amino-acid form supports reproducible synthesis of labeled peptide constructs, ensuring that the fluorinated tag is introduced at a known position and can be monitored with high specificity in analytical readouts.
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