Boc-2,4-Difluoro-D-Phenylalanine is a protected, non-natural amino acid derivative featuring a phenylalanine backbone bearing two fluorine substituents at the 2- and 4-positions of the aromatic ring and the D stereochemical configuration at the α-carbon. The molecule contains an α-amino group masked as a Boc (tert-butoxycarbonyl) carbamate and a free carboxyl group, while the fluorinated aryl side chain provides increased electron-withdrawing character and altered steric and hydrogen-bonding behavior compared with unsubstituted phenylalanine. This protected analogue is used in peptide synthesis and structure-activity studies where incorporation of fluorinated phenylalanine residues is needed to probe conformational effects, side-chain electronics, and chemical labeling or analytical readouts associated with aryl fluorination.
CAT No: CP12705
Boc-2,4-Difluoro-D-Phenylalanine is a D-configured, non-proteinogenic phenylalanine analog bearing two fluorine atoms at the 2- and 4-positions of the aromatic ring, supplied as a Boc-protected amino acid building block. The combination of the Boc carbamate on the amino group and the difluoro-substituted aryl side chain makes it a useful reagent for incorporating conformationally and electronically tuned aromatic residues into peptide-like structures. In medicinal chemistry and peptide drug discovery workflows, aryl fluorination is frequently used to modulate physicochemical properties and to support structure-activity relationship (SAR) studies through systematic side-chain variation.
1. Peptide Library Building
Boc-2,4-Difluoro-D-Phenylalanine is commonly used by custom peptide synthesis groups and medicinal chemistry teams to assemble peptide libraries where D-amino acid incorporation and aromatic fluorination are used to probe sequence effects and side-chain electronics. The Boc protection supports standard protected-amino-acid handling in peptide assembly workflows, enabling researchers to generate analog series that differ specifically at the substituted phenylalanine position. This product's difluoro-aryl motif is particularly valuable when developers want a chemically defined aromatic variant rather than relying on unsubstituted phenylalanine, allowing tighter control over steric and electronic features across a library.
2. Peptidomimetic SAR Development
Boc-2,4-Difluoro-D-Phenylalanine supports peptidomimetic and small-molecule lead optimization programs that rely on systematic SAR around aromatic side chains. Fluorine substitution at defined ring positions provides a handle for tuning lipophilicity, metabolic stability trends, and conformational preferences in a way that is straightforward to compare across analogs, while the D-configuration helps introduce stereochemical diversity distinct from proteinogenic L-residues. Medicinal chemistry groups use this building block to prepare analogs for structure-property correlation studies, where the difluoro-phenylalanine residue serves as a precise chemical variable within a larger scaffold.
3. Chiral Building Block For Synthesis
Boc-2,4-Difluoro-D-Phenylalanine is used as a chiral amino acid intermediate for downstream synthesis of fluorinated aromatic amino acid derivatives and peptide-like intermediates where stereochemical integrity is required. Process and research chemists often select D-configured, Boc-protected building blocks to manage reactivity and to maintain consistent stereochemical outcomes during stepwise assembly. The difluoro-substituted phenyl side chain further makes it a practical choice for preparing fluorinated analogs that are difficult to obtain by late-stage modification, supporting workflows that prioritize modular, building-block-based synthesis for analog generation.
4. Analytical Reference Standards
Boc-2,4-Difluoro-D-Phenylalanine is also used in analytical method development and reference material preparation for workflows that require well-defined fluorinated amino acid content. In LC-MS and related characterization pipelines, having an authenticated, protected chiral amino acid standard helps teams verify identity and monitor incorporation of the difluoro-phenylalanine residue during peptide or peptidomimetic synthesis. Researchers in chemical development and analytical science value this compound when they need a structurally specific reference that reflects the exact substituted aromatic motif used in their target structures.
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