Cbz-3,4-Difluoro-L-Phenylalanine is a protected amino acid derivative featuring an L-phenylalanine backbone bearing two fluorine substituents at the 3- and 4-positions of the aromatic side chain. The molecule contains both an amino group and a carboxyl group, with the amino functionality protected as a Cbz (benzyloxycarbonyl) carbamate, while the difluorinated phenyl ring provides distinct electronic and steric characteristics relative to unsubstituted phenylalanine. It is used in peptide chemistry and structure-activity or binding studies where incorporation of an aryl-difluoro phenylalanine residue is required, and the Cbz protection supports chemoselective handling of the amino functionality during stepwise synthesis.
CAT No: CP13008
Cbz-3,4-Difluoro-L-Phenylalanine is an L-phenylalanine derivative bearing two fluorine atoms on the aromatic ring at the 3- and 4-positions, combined with a benzyloxycarbonyl (Cbz) protecting group on the amino functionality. The molecule retains the stereogenic α-carbon of the L-amino acid, providing a defined chiral center for stereocontrolled peptide coupling and downstream derivatization. The CbZ group introduces an N-protected carbamate that can be removed under hydrogenolysis conditions, while the difluorinated phenyl side chain provides strong electron-withdrawing character and altered hydrophobic and aromatic interaction profiles. As a chiral, N-protected amino acid building block, it functions as a practical intermediate for protected amino acid synthesis, peptidomimetic construction, and fluorinated aromatic incorporation into peptide-like scaffolds.
1. Peptide Synthesis
Cbz-3,4-Difluoro-L-Phenylalanine is applied in peptide building and protected amino acid synthesis where N-Cbz protection supports standard peptide coupling workflows. The α-amino acid backbone and Cbz-protected amine enable formation of amide bonds while maintaining the L-configuration at the stereogenic center during chain assembly. The 3,4-difluorophenyl side chain can be incorporated as a fluorinated aromatic residue to tune conformational preferences and aromatic interactions in peptide sequences. The resulting fluorinated peptides and peptide fragments can serve as research-grade materials for studying structure-dependent properties and for generating analog libraries in synthetic peptide chemistry.
2. Peptidomimetics And SAR
Cbz-3,4-Difluoro-L-Phenylalanine is utilized in peptidomimetic construction and structure-activity relationship studies where aromatic fluorination provides a handle for modulating binding-site contacts. The difluorinated phenyl ring contributes distinct electronic effects and can influence π-stacking, polarizability, and local hydrophobicity compared with non-fluorinated phenylalanine analogs. The Cbz-protected amino acid form supports sequential derivatization into constrained or modified peptide-like scaffolds via peptide coupling and subsequent deprotection steps. Downstream analogs prepared from this residue can be used to map how fluorinated aromatic substitutions affect molecular recognition patterns in SAR workflows.
3. Chiral Amino Acid Intermediate
Cbz-3,4-Difluoro-L-Phenylalanine is employed as a chiral amino acid intermediate for stereoselective synthesis of fluorinated building blocks used in fine chemical and medicinal chemistry manufacturing routes. The L-stereocenter and N-Cbz carbamate provide a stable protected form that can be carried through multi-step sequences before functional group unveiling. The difluoro-substituted aromatic side chain can be retained to generate downstream fluorinated derivatives, including substituted aromatic fragments and peptide-derived intermediates for further functionalization. The compound's defined stereochemistry and protected amine make it suitable for controlled incorporation of fluorinated phenylalanine motifs into larger chiral frameworks.
4. Chemical Biology Labeling
Cbz-3,4-Difluoro-L-Phenylalanine is suitable for chemical biology research requiring fluorinated aromatic residues as structural probes in peptide-based biomolecule modification. The protected amino acid format supports incorporation into peptide conjugates where subsequent Cbz removal enables further coupling to targeting ligands or biomolecular scaffolds. The 3,4-difluorophenyl group can function as a spectroscopically and chemically distinctive aromatic element, enabling tracking of incorporation and supporting studies of binding or localization using fluorinated residue signatures. The resulting labeled peptides and conjugation intermediates can be used to generate defined biomolecular constructs for mechanistic investigations and analytical method development.
5. Pharmaceutical Intermediate Preparation
Cbz-3,4-Difluoro-L-Phenylalanine is applied in pharmaceutical intermediate preparation where protected amino acid chemistry supports scalable synthesis of fluorinated peptide fragments and peptidomimetic precursors. The Cbz-protected amine and intact α-carboxyl functionality align with industrially relevant peptide coupling strategies that convert amino acid building blocks into amide-containing intermediates. The difluorinated aromatic side chain provides a chemically stable motif that can be carried into drug-like scaffold synthesis while enabling downstream transformations such as deprotection and further functional group elaboration. The compound can therefore serve as a process-compatible chiral input for manufacturing routes that require incorporation of fluorinated phenylalanine residues into larger, defined molecular entities.
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