Cbz-4-Fluoro-D-Phenylalanine is a Cbz-protected, non-natural amino acid derivative featuring a fluorinated phenylalanine side chain with a 4-fluoro substituent on the aromatic ring and a D-stereochemical configuration as indicated by the product name. The molecule contains a Cbz (benzyloxycarbonyl) carbamate protecting group on the amino functionality, while the carboxyl group remains available as the free acid for coupling chemistry, and the aromatic side chain bears a fluorine substituent that modulates electronic and physicochemical properties. In peptide and amino acid synthesis, this protected analogue is used as a building block to introduce a 4-fluoro-substituted phenylalanine residue into peptides or peptide-related intermediates, and the fluorinated aromatic handle can support structure-activity studies and analytical labeling or characterization by providing a distinct chemical signature.
CAT No: CP14609
Cbz-4-Fluoro-D-Phenylalanine is a Cbz-carbamate-protected D-phenylalanine derivative bearing a para-fluoro substituent on the aromatic ring. The molecule combines a stereochemically defined chiral center at the amino acid alpha-position with an aryl fluorine handle that can participate in electrophilic aromatic substitution, nucleophilic aromatic substitution under appropriate conditions, or serve as a stable fluorinated motif in structure-activity relationship studies. The benzyloxycarbonyl (Cbz) group masks the amino functionality for controlled peptide coupling chemistry and can be removed by hydrogenolysis to regenerate the free amine when needed. The presence of the aromatic side chain and the fluorine substituent modulates polarity and can influence conformational preferences and downstream derivatization pathways in peptide and peptidomimetic synthesis.
1. Peptide Synthesis
Cbz-4-Fluoro-D-Phenylalanine is employed in peptide building workflows where a protected, stereodefined amino acid is required for amide bond formation. The Cbz-protected amine supports standard peptide coupling strategies while the D-configuration enables incorporation of D-amino acid residues into peptide chains to tune backbone stereochemistry and proteolytic stability. The para-fluoro aromatic side chain remains intact during coupling, enabling retention of the fluorinated pharmacophore through chain assembly. Downstream deprotection to the free amine can be integrated into iterative solid-phase or solution-phase synthesis to generate fluorinated peptide analogs for biochemical research and medicinal chemistry programs.
2. Peptidomimetics And SAR
Cbz-4-Fluoro-D-Phenylalanine is suitable for peptidomimetic construction and SAR studies that require a fluorinated aromatic substituent positioned on a D-amino acid scaffold. The aryl fluorine provides a chemically robust substituent that can influence binding interactions via inductive effects and can serve as a tracer or reference handle in comparative analog series. The protected amino acid form supports selective incorporation into constrained frameworks, including cyclized peptides and scaffolded mimetics where side-chain electronics and stereochemistry are key variables. The resulting fluorinated D-amino acid motifs can be carried into structure-activity relationship investigations and fragment-to-lead optimization by enabling systematic modification of aromatic substitution patterns.
3. Chiral Intermediate Synthesis
Cbz-4-Fluoro-D-Phenylalanine is used as a chiral amino acid intermediate for stereocontrolled synthesis of fluorinated building blocks in fine chemical production. The D-configuration at the alpha-carbon provides a defined stereochemical element that can be transferred into downstream derivatives, including activated esters, amide-forming intermediates, or side-chain functionalized analogs after appropriate deprotection and conversion. The Cbz group acts as an orthogonal protection strategy relative to other functional group manipulations, allowing sequential transformations while maintaining the stereochemical integrity of the amino acid core. Industrial and research settings can apply this intermediate to prepare fluorinated chiral fragments for medicinal chemistry, chemical biology probes, and process-compatible intermediate supply chains.
4. Chemical Biology Probes
Cbz-4-Fluoro-D-Phenylalanine is applicable to chemical biology research where fluorinated aromatic residues are introduced to modulate molecular recognition and enable analytical tracking. The stable C-F bond on the para position can be leveraged for spectroscopic characterization and for designing probes that maintain fluorine through peptide assembly. The Cbz-protected amine enables controlled incorporation into peptide-based probes, while D-stereochemistry can help adjust protease resistance and alter cellular uptake behavior of peptide conjugates without changing the fluorinated side chain identity. The resulting fluorinated D-amino acid-containing constructs can serve as reference standards, mechanistic probes, or labeled components for studying biomolecular interactions.
5. Pharmaceutical Intermediate Preparation
Cbz-4-Fluoro-D-Phenylalanine is relevant to pharmaceutical intermediate preparation for manufacturing of fluorinated amino acid derivatives used in peptide-like active ingredient candidates. The protected amino acid functionality supports conversion to coupling-ready forms and later deprotection to furnish the corresponding free D-4-fluorophenylalanine for incorporation into larger synthetic sequences. The fluorinated aromatic side chain can be retained as a defined substituent through industrially scalable synthetic steps, supporting consistent impurity profiles and reproducible scaffold construction. The compound's Cbz-protected design aligns with protecting-group strategies commonly applied in process chemistry to manage chemoselectivity during intermediate synthesis and downstream API-related assembly.
6. Analytical Standards and Method Development
Cbz-4-Fluoro-D-Phenylalanine is utilized as an analytical reference material for method development and characterization of fluorinated peptide intermediates. The defined D-stereochemistry and the Cbz-protected amino functionality provide a discriminating standard for chromatographic separation, mass spectrometric identification, and impurity mapping in amino acid and peptide workflows. The para-fluoro aromatic group enhances detectability and supports targeted analytical transitions, aiding verification of incorporation and monitoring of deprotection or coupling steps. The compound can also function as a structural benchmark in analytical research for validating derivatization outcomes and confirming stereochemical integrity in fluorinated amino acid derivative series.
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