Cbz-3-Fluoro-D-Phenylalanine is a Cbz-protected, non-natural amino acid derivative featuring a phenylalanine backbone with a fluorine substituent at the 3-position of the aromatic ring and a D-stereochemical configuration. The molecule contains an N-Cbz carbamate protecting group and a free carboxylic acid, with the aromatic side chain bearing the fluorine functional handle that can influence electronic properties and hydrophobic/steric interactions during peptide incorporation. In peptide chemistry, it functions as a protected amino acid building block for stepwise synthesis and structure-activity studies, and the aryl fluorine can be used as a chemically distinctive substituent for analytical characterization and labeling-related workflows.
CAT No: CP14509
Cbz-3-Fluoro-D-Phenylalanine is a D-configured phenylalanine derivative bearing a benzyl oxycarbonyl (Cbz) protecting group on the amino functionality and a fluorine substituent at the 3-position of the aromatic ring. The molecule combines a stereogenic alpha-carbon with an aryl fluoride, providing a defined chiral amino acid building block while introducing a handle for subsequent aromatic functional transformations. The Cbz carbamate can be removed under hydrogenolysis conditions, enabling compatibility with protected amino acid synthesis and peptide coupling workflows that rely on orthogonal deprotection. The aryl C-F bond influences electronic properties and can support downstream derivatization strategies used in structure-focused medicinal chemistry and peptidomimetic design.
1. Peptide Synthesis
Cbz-3-Fluoro-D-Phenylalanine is applied in peptide building workflows where a protected, chiral amino acid is required for controlled incorporation into peptide chains. The Cbz-protected amine supports standard peptide coupling chemistry at the N-terminus after deprotection, while the D-stereochemistry enables access to D-amino acid containing peptides that resist proteolysis and alter conformational preferences. The 3-fluoro aromatic side chain can be retained through peptide assembly, allowing late-stage functionalization of the aryl motif on the peptide scaffold. The resulting fluorinated D-phenylalanine peptide analogs can be used as biochemical research reagents and as intermediates toward peptidomimetic libraries.
2. Peptidomimetics And SAR
Cbz-3-Fluoro-D-Phenylalanine is used in structure-activity relationship studies and peptidomimetic construction where aryl substitution patterns are tuned to probe molecular recognition. The fluorine substituent at the aromatic 3-position provides a chemically stable substituent that can modulate lipophilicity, hydrogen-bonding behavior through inductive effects, and metabolic stability trends in analog series. The D-configuration supports stereochemical control in scaffold design, enabling comparisons between L- and D-analog conformations and side-chain orientations. The protected amino acid form supports stepwise synthesis of fluorinated analogs that can feed SAR campaigns and guide fragment-to-lead refinement in medicinal chemistry programs.
3. Side-Chain Functionalization
Cbz-3-Fluoro-D-Phenylalanine serves as an aromatic C-F functionalization precursor in synthetic organic chemistry and downstream intermediate preparation. The aryl fluoride can participate in substitution or cross-coupling strategies to introduce alternative substituents on the phenyl ring while preserving the amino acid backbone for continued derivatization. The Cbz carbamate protects the amine during side-chain transformation steps, supporting orthogonal handling of the functional groups and reducing undesired polymerization or coupling at the nitrogen. The resulting substituted phenylalanine derivatives can be carried forward into further peptide coupling, linker installation, or scaffold diversification for chemical biology and industrial fine chemical synthesis.
4. Chemical Biology Probes
Cbz-3-Fluoro-D-Phenylalanine is suitable for chemical biology research requiring defined stereochemistry and a fluorinated aromatic reporter motif. The protected amino acid format enables incorporation into peptide-based probes where N-protection and controlled deprotection allow sequential assembly of labeled or functionalized biomolecule fragments. The D-amino acid stereocenter can influence binding mode and stability in enzyme-interaction studies, while the aryl fluoride provides a distinct chemical signature for analytical tracking and structural confirmation. Fluorinated D-phenylalanine-containing constructs can be used to generate substrate mimics, binding probes, or mechanistic reagents that support structure-resolved biochemical investigations.
5. Pharmaceutical Intermediate Preparation
Cbz-3-Fluoro-D-Phenylalanine is used as a chiral intermediate in pharmaceutical intermediate preparation and specialty chemical production where fluorinated amino acid motifs are required. The Cbz-protected amine and the stereogenic D-alpha-carbon make the compound compatible with protected amino acid synthesis sequences that feed into larger molecule assembly, including peptide-like fragments and constrained heteroaromatic systems. The aryl fluoride can be retained as a functional handle through intermediate stages, enabling later diversification into substituted analogs for process-driven route development. The compound's defined structure supports reproducible downstream transformations typical of industrial chemical manufacturing pipelines for chiral building blocks.
6. Protected Amino Acid Chemistry
Cbz-3-Fluoro-D-Phenylalanine is applied in protected amino acid chemistry as a Cbz-protected, stereodefined amino acid derivative for orthogonal protection and coupling strategies. The carbamate-protected amine can be selectively removed to generate a reactive amino functionality for peptide coupling or further derivatization, while the aromatic fluorine remains stable under many peptide-manufacturing conditions. The combination of a D-stereocenter and protected nitrogen supports stereochemically controlled synthesis of unnatural amino acid sequences and chiral intermediates for method development. The compound can be employed to prepare fluorinated peptide building blocks and chiral analogs that support synthetic methodology studies and industrial fine chemical synthesis of amino acid-derived scaffolds.
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