Cbz-3,4-Difluoro-D-Phenylalanine is a Cbz-protected, non-natural amino acid derivative bearing a D-phenylalanine backbone with two fluorine atoms at the 3 and 4 positions of the aromatic side chain. The molecule contains an N-Cbz carbamate (benzyl oxycarbonyl protecting group) and free carboxyl functionality, with the aromatic ring substituted by fluorine to modulate electronic character and affect side-chain hydrophobicity and hydrogen-bonding patterns. As a protected amino acid building block, it is used in amino acid and peptide synthesis workflows where the Cbz group helps control chemoselectivity during stepwise coupling and the difluoro-substituted phenyl side chain provides a fluorinated handle for structure-activity studies, chemical biology labeling strategies, or analytical method development.
CAT No: CP13009
Cbz-3,4-Difluoro-D-Phenylalanine is a D-configured phenylalanine derivative bearing a benzyloxycarbonyl (Cbz) protecting group on the amino functionality and two fluorine atoms on the aromatic ring at the 3,4-positions. The chiral alpha-carbon stereocenter and the electron-withdrawing difluoro-substituted phenyl ring together create a distinct reactivity and conformational profile compared with unsubstituted phenylalanine analogs. The Cbz carbamate is compatible with standard peptide-coupling workflows while remaining stable under many coupling and derivatization conditions, yet can be removed by hydrogenolysis to reveal a free amine for subsequent assembly. The aromatic difluoro pattern can participate in halogen-influenced molecular recognition and can serve as a metabolically and physicochemically tuned motif in peptide analogs and chiral building blocks.
1. Peptide Synthesis
Cbz-3,4-Difluoro-D-Phenylalanine is applied in peptide building block preparation where a protected, stereodefined amino acid is required for controlled amide bond formation. The Cbz-protected amine supports peptide coupling chemistry, while the carboxylate functionality enables incorporation at internal positions or at the amino-acid residue level during protected amino acid synthesis. The D-configuration provides stereochemical control for generating D-amino acid-containing peptides, which can be used to probe backbone effects and improve resistance to proteolysis in peptide science contexts. The difluoro-substituted phenyl side chain can be retained through synthesis as a defined aromatic pharmacophore for downstream peptide analog construction and structure-activity relationship studies.
2. Chiral Amino Acid Intermediate
Cbz-3,4-Difluoro-D-Phenylalanine functions as a chiral amino acid intermediate for stereoselective synthesis of fluorinated aromatic derivatives and peptidomimetic scaffolds. The fixed D-stereochemistry at the alpha-carbon enables downstream derivatization without scrambling the stereocenter, supporting reproducible chiral fragment generation for medicinal chemistry and process chemistry intermediate preparation. The Cbz carbamate provides a handle for orthogonal protection strategies, allowing selective deprotection and subsequent functionalization cycles when assembling multi-functional molecules. The 3,4-difluoro phenyl motif can be carried into higher-complexity intermediates to tune electronic properties and molecular recognition patterns in synthetic organic chemistry campaigns.
3. Peptidomimetics And SAR
Cbz-3,4-Difluoro-D-Phenylalanine is used in peptidomimetic construction and SAR-focused library synthesis where a fluorinated aromatic side chain is needed as a modifiable binding element. The difluoro substitution pattern on the phenyl ring provides a defined steric and electronic environment that can influence hydrogen bonding, dipole interactions, and aromatic interactions in bioactive conformations. The protected amino acid format supports stepwise assembly into peptide analogs, enabling systematic comparison of aromatic substitution patterns while maintaining the same stereochemical backbone. The resulting fluorinated D-phenylalanine-containing analogs can be employed as biochemical research intermediates for structure-activity relationship studies and molecular design workflows.
4. Chemical Biology Labeling
Cbz-3,4-Difluoro-D-Phenylalanine can be applied in chemical biology research requiring incorporation of a defined aromatic fluorinated residue into peptide probes or protein-targeting constructs. The Cbz-protected amine and carboxyl functionality enable controlled incorporation into peptide segments that can later be deprotected and functionalized for conjugation to tags, linkers, or affinity handles. The D-amino acid configuration can help modulate protease susceptibility and stability of labeled biomolecular probes, supporting longer-lived reagent formats in experimental workflows. The difluoro phenyl group serves as a chemically defined aromatic unit that can be retained during conjugation steps to maintain consistent structure in biomolecule modification studies.
5. Pharmaceutical Intermediate Preparation
Cbz-3,4-Difluoro-D-Phenylalanine is suitable for pharmaceutical intermediate preparation where fluorinated, stereodefined amino acid derivatives are required for drug candidate synthesis and analog manufacturing routes. The Cbz carbamate protection strategy supports compatibility with peptide coupling and intermediate assembly operations, while enabling controlled deprotection to access the free amine for further transformations. The D-phenylalanine stereocenter and difluoro aromatic ring enable downstream synthesis of fluorinated peptide-like compounds and chiral fragments used in fine chemical production. The compound's defined functional group set supports scalable process chemistry planning for protected amino acid chemistry and subsequent conversion into higher-order intermediates used in industrial synthetic sequences.
6. Specialty Chemical Production
Cbz-3,4-Difluoro-D-Phenylalanine can be employed in specialty chemical production requiring halogenated aromatic amino acid derivatives as defined building blocks. The protected carbamate and carboxy functionality allow the material to participate in stepwise synthetic routes that generate fluorinated amide-containing products, including peptide analogs and aromatic-functionalized intermediates. The difluoro-substituted phenyl side chain provides a stable motif that can be carried through manufacturing steps without altering the aromatic substitution pattern, supporting consistent batch-to-batch structural definition. The compound thereby serves as a chiral amino acid-based intermediate for industrial chemistry where fluorinated stereodefined scaffolds are needed for functional molecule generation and downstream synthetic diversification.
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