Cbz-2,4-Difluoro-D-Phenylalanine is a protected, non-natural amino acid derivative featuring a D-phenylalanine backbone bearing two fluorine substituents at the 2- and 4-positions of the aromatic side chain. The molecule contains a Cbz (benzyloxycarbonyl) protecting group on the amino functionality while retaining a free carboxylic acid, and the difluoro-substituted phenyl ring provides altered electronic and steric properties relative to unsubstituted phenylalanine. It is used in peptide synthesis and structure-activity studies where the Cbz-protected amino group supports controlled incorporation of the fluorinated residue and the side-chain fluorination supports physicochemical tuning and analytical differentiation in labeling or characterization workflows.
CAT No: CP12709
Cbz-2,4-Difluoro-D-Phenylalanine is a chiral, N-Cbz-protected D-phenylalanine derivative bearing two fluorine substituents at the 2- and 4-positions of the phenyl ring. The molecule combines an aromatic side chain with strong inductive effects from the fluorinated ring, while the benzyloxycarbonyl (Cbz) group provides a stable N-protection handle that can be removed under hydrogenolysis-compatible conditions. The D stereocenter at the alpha carbon supports stereochemically defined peptide bond formation and downstream stereochemical retention or controlled inversion depending on the coupling strategy. The difluoroaryl motif contributes to predictable electrophilic aromatic behavior and can modulate lipophilicity, conformational preferences, and binding-site interactions in peptide-like scaffolds and small-molecule analogs.
1. Peptide Synthesis
Cbz-2,4-Difluoro-D-Phenylalanine is applied in peptide building and protected amino acid synthesis workflows where the Cbz-protected amine and the free carboxyl functionality enable standard peptide coupling chemistry. The D-configuration at the alpha carbon supports incorporation of a stereodefined residue into linear peptides, cyclic peptides, and protected peptide fragments used for structure-activity relationship studies. The fluorinated phenyl side chain can be carried through chain elongation to furnish peptides with altered aromatic electronics and steric/electronic profiles relative to non-fluorinated analogs. The resulting fluorinated peptide intermediates can be further deprotected and assembled into higher-order constructs for synthetic methodology development and SAR-focused library generation.
2. Chiral Amino Acid Intermediate
Cbz-2,4-Difluoro-D-Phenylalanine serves as a chiral amino acid intermediate for stereocontrolled fine chemical synthesis and chiral building block development. The combination of a single alpha stereocenter and a protected N-terminus (Cbz) supports predictable reactivity under peptide-coupling and functional-group transformation conditions while limiting undesired side reactions from the amine. The difluoroaryl substituents provide a chemically informative handle for downstream derivatization, including analog design routes that probe aromatic substitution patterns. The compound can be employed to prepare a range of D-configured fluorinated amino acid derivatives and peptide-like fragments used in chiral synthesis planning and intermediate supply for research and manufacturing-scale campaigns.
3. Side-Chain Functionalization
Cbz-2,4-Difluoro-D-Phenylalanine is utilized in side-chain functionalization strategies for generating fluorinated aromatic variants and peptidomimetic scaffolds. The difluoro substitution pattern on the phenyl ring can influence subsequent synthetic steps such as electrophilic aromatic substitution, cross-coupling-compatible transformations, or incorporation into heteroaromatic-forming sequences when converted through appropriate functional group interconversions. The Cbz-protected amine maintains chemoselectivity during manipulations that target the aromatic ring or carboxyl-derived intermediates, enabling staged protection/deprotection logic. Fluorinated side-chain-modified derivatives produced from this amino acid intermediate can be used to tune physicochemical properties and molecular recognition features in synthetic organic chemistry and applied scaffold development.
4. Drug Discovery Scaffolds
Cbz-2,4-Difluoro-D-Phenylalanine is applied in medicinal chemistry and drug discovery programs that rely on fluorinated amino acid residues to modulate binding interactions in peptide-like inhibitors and small-molecule mimetics. The D stereochemistry and N-Cbz protection facilitate incorporation into constrained or semi-peptide scaffolds where stereochemical identity is critical for conformational and binding-site alignment. The 2,4-difluoroaryl side chain can be leveraged to tune aromatic electronics and hydrophobic/aromatic surface characteristics, supporting SAR studies that compare substitution patterns and stereochemical effects. The compound can function as a defined intermediate for preparing analog series that include protected peptide fragments, peptidomimetics, and fluorinated building blocks for iterative structure refinement.
5. Pharmaceutical Manufacturing Intermediates
Cbz-2,4-Difluoro-D-Phenylalanine is suitable for pharmaceutical intermediate preparation where controlled protection of the amino functionality and stereodefined residue incorporation are required for downstream synthesis. The Cbz group provides a robust N-protection strategy during coupling and intermediate handling, while the amino acid framework supports conversion into activated derivatives for stepwise assembly into larger protected sequences. The difluoroaryl motif can be carried through manufacturing routes to produce fluorinated peptide intermediates and final fluorinated active pharmaceutical ingredient (API) precursors or key intermediates used in fine chemical production. The compound's defined structure supports reproducible intermediate generation for scale-up planning in industrial synthetic chemistry settings that require consistent stereochemical and functional group profiles.
6. Analytical Standards And SAR Studies
Cbz-2,4-Difluoro-D-Phenylalanine is used for analytical research and reference material preparation in studies that monitor fluorinated amino acid incorporation and peptide assembly outcomes. The presence of a Cbz-protected amine and the difluoroaryl side chain provides distinct chromatographic and spectroscopic signatures that can assist in identity confirmation, impurity profiling, and method development for amino acid and peptide intermediates. The D stereocenter enables stereospecific comparisons between enantiomeric or diastereomeric analogs in SAR studies and synthetic route evaluation. Fluorinated derivatives derived from this compound can further serve as standards or calibration components for characterizing peptide-like products and validating structural integrity during applied synthetic and biochemical research workflows.
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