3,5-Difluoro-D-Phenylalanine is a non-natural, stereochemically defined amino acid derivative featuring a D-configuration at the alpha carbon and a phenylalanine scaffold bearing two fluorine atoms at the 3 and 5 positions of the aromatic side chain. The molecule contains a free amino group and a carboxyl group for acid-base behavior and peptide-coupling chemistry, while the difluoro-substituted phenyl ring provides altered electronic and hydrophobic characteristics relative to unsubstituted phenylalanine. It is used in peptide synthesis and structure-activity or structure-property studies where fluorinated, stereodefined amino acid analogues provide a chemical handle for tuning aromatic interactions and supporting analytical differentiation in chemical biology and biomaterials research.
CAT No: CP13102
3,5-Difluoro-D-Phenylalanine is a D-configured, non-proteinogenic phenylalanine analog bearing two fluorine atoms at the 3 and 5 positions of the aromatic ring. This halogenated side chain increases the compound's chemical distinctiveness for medicinal chemistry and SAR studies, while the D-stereochemistry provides a stereochemically defined building block for peptide and peptidomimetic design. Researchers commonly use this fluorinated amino acid to introduce controlled electronic and steric effects into synthetic sequences and to support structure-property investigations where aromatic fluorination is a key variable.
1. Peptidomimetic Building Block
3,5-Difluoro-D-Phenylalanine is used as a stereochemically defined building block for incorporating D-phenylalanine analogs into peptides and peptidomimetics. Medicinal chemistry groups and custom peptide manufacturers rely on it to probe how aromatic fluorination (3,5-difluoro substitution) and D-configuration influence conformational preferences, local physicochemical properties, and overall sequence behavior in synthetic constructs. In practice, the compound is selected when the target design requires a non-natural, fluorinated aromatic residue rather than a standard phenylalanine, enabling systematic variation of side-chain electronics while maintaining a well-defined stereocenter for downstream assembly workflows.
2. Structure-Activity Relationship Studies
3,5-Difluoro-D-Phenylalanine supports SAR campaigns where aromatic fluorine substitution patterns are treated as explicit chemical variables. Drug discovery teams use this analog to compare how 3,5-difluoro substitution on an otherwise phenylalanine-like scaffold affects measured properties in binding or functional assays performed on peptide-based or peptidomimetic leads. The D-configuration further allows stereochemical control during library synthesis, helping researchers separate stereochemical effects from substitution effects when mapping structure to activity. Because fluorinated amino acid analogs are frequently pursued to tune aromatic character and interaction profiles, this product is commonly chosen for focused analog series rather than broad, undifferentiated amino acid screening.
3. Chemical Biology Probe Synthesis
3,5-Difluoro-D-Phenylalanine is incorporated into chemically defined peptide probes to introduce a stable, non-natural aromatic motif that can be tracked by analytical readouts and used as a probe residue in mechanistic studies. Chemical biology teams use fluorinated D-amino acid analogs to create probe libraries where the aromatic ring's fluorination provides a distinctive chemical signature for characterization and for distinguishing probe-containing constructs from closely related controls. This approach is particularly relevant when researchers need a residue that is not native to proteins and that can be embedded into synthetic peptides used for target engagement studies, substrate analog work, or mechanistic mapping where defined side-chain chemistry matters.
4. Pharmaceutical Intermediate Development
3,5-Difluoro-D-Phenylalanine serves as a practical chiral intermediate for downstream synthesis of fluorinated D-amino acid derivatives used in pharmaceutical intermediate development. Process and synthetic chemistry teams select this compound when a defined 3,5-difluoro aromatic motif and D-stereochemistry must be carried through to later-stage intermediates for peptide-like candidates or fluorinated small-molecule scaffolds. Its role is typically to provide a controlled stereochemical handle and a chemically distinctive aromatic unit that can be transformed into protected or activated derivatives as required by the specific manufacturing route, supporting consistent analog generation during lead optimization.
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