Cbz-2,4,6-Trifluoro-L-Phenylalanine is a Cbz-protected, fluorinated amino acid derivative in which the phenylalanine side chain bears three fluorine substituents at the 2, 4, and 6 positions, retaining an L stereochemical designation at the α-carbon. The molecule contains a Cbz (benzyloxycarbonyl) protecting group on the amino functionality, a free carboxylic acid group, and a substituted aromatic ring whose electron-withdrawing fluorines modulate side-chain polarity and hydrophobic character for peptide incorporation studies. In synthesis, the protected amino group supports stepwise peptide assembly while the fluorinated aromatic side chain functions as a structural handle for preparing modified peptides and for structure-activity or analytical studies that distinguish fluorinated phenylalanine analogues.
CAT No: CP17008
Cbz-2,4,6-Trifluoro-L-Phenylalanine is an L-phenylalanine derivative bearing a benzyloxycarbonyl (Cbz) protecting group on the amino function and three fluorine atoms at the 2, 4, and 6 positions of the aromatic ring. The molecule retains the chiral alpha-carbon stereochemistry characteristic of L-amino acids, while the electron-withdrawing trifluorinated phenyl side chain modulates aromatic reactivity, polarity, and metabolic stability-relevant physicochemical behavior. The Cbz carbamate provides a robust N-protection strategy compatible with peptide coupling conditions, and the aromatic fluorines serve as handles for downstream derivatization or as defined substituent patterns for SAR-oriented molecular design. The compound functions as a chiral, N-protected amino acid building block and intermediate for constructing fluorinated peptide analogs and other fluorinated aromatic frameworks.
1. Peptide Synthesis
Cbz-2,4,6-Trifluoro-L-Phenylalanine supports peptide building-block workflows in solid-phase or solution-phase assembly where N-protection is required for controlled amide bond formation. The Cbz-protected amine and the amino acid carboxyl functionality enable standard peptide coupling chemistries after activation of the acid, while the L-configuration preserves stereochemical fidelity at the alpha-carbon during chain elongation. The trifluorinated phenyl side chain can be incorporated as a defined aromatic motif to tune hydrophobicity and electronic character across peptide sequences. The resulting fluorinated peptide products can be used as biochemical research intermediates, allowing systematic comparison of analogs that differ only in aromatic substitution patterns.
2. Peptidomimetics And SAR Studies
Cbz-2,4,6-Trifluoro-L-Phenylalanine is applicable to peptidomimetic construction and structure-activity relationship studies where a fluorinated aromatic side chain provides a predictable electronic and steric signature. The 2,4,6-trifluoro substitution pattern can influence conformational preferences and intermolecular interactions, and the preserved L-amino acid backbone supports incorporation into constrained peptide-like scaffolds. The Cbz carbamate can be removed orthogonally under conditions compatible with other protecting groups, facilitating late-stage diversification of N-terminus chemistry. Downstream derivatives prepared from this intermediate can serve as defined SAR probes, enabling targeted evaluation of how fluorinated aromatic electronics affect binding motifs in chemical biology campaigns.
3. Side-Chain Functionalization
Cbz-2,4,6-Trifluoro-L-Phenylalanine can be used for side-chain functionalization strategies that exploit the fluorinated aromatic ring as a stable, substitution-pattern-defined platform. The electron-deficient trifluorinated phenyl group can participate in subsequent synthetic transformations that introduce additional substituents while maintaining the fluorine-defined substitution geometry, supporting synthesis of fluorinated analog libraries. The protected amino acid format allows orthogonal handling of the nitrogen and carboxyl groups, so side-chain modifications can be planned without premature interference from free amine reactivity. The resulting functionalized aromatic amino acid derivatives can then be carried forward into peptide analog construction, fragment elaboration, or specialized building-block preparation for fine chemical synthesis.
4. Protein Engineering
Cbz-2,4,6-Trifluoro-L-Phenylalanine is suitable for protein engineering and chemical protein modification programs that require incorporation of fluorinated aromatic residues into polypeptide contexts. The L-configuration and amino acid backbone enable compatibility with peptide synthesis routes used to generate defined protein segments or labeled protein mimics, while the Cbz group provides a controllable N-protection handle during chain assembly. The trifluorinated phenyl side chain can be used to create well-defined aromatic environments in engineered sequences, supporting studies of structure-function relationships in protein-like systems. The compound thereby serves as a chiral amino acid intermediate for generating fluorinated polypeptide constructs used in biochemical research and applied molecular design.
5. Pharmaceutical Intermediate Preparation
Cbz-2,4,6-Trifluoro-L-Phenylalanine supports pharmaceutical intermediate preparation where fluorinated aromatic amino acid motifs are used to access drug-like chemical space in synthetic chemistry. The Cbz-protected amine and carboxylic acid functionality allow conversion into activated derivatives for downstream coupling steps, enabling preparation of fluorinated amide-containing intermediates and peptide-derived scaffolds. The trifluorinated aromatic ring contributes a chemically stable substitution pattern that can be retained through multi-step routes, supporting manufacturing-relevant synthesis planning for fluorinated fine chemicals. The compound can be employed as a chiral building block in process chemistry intermediate sequences that lead to fluorinated heteroaryl/aryl-containing structures and peptidic or peptidomimetic intermediates.
6. Analytical Research Standards
Cbz-2,4,6-Trifluoro-L-Phenylalanine is useful for analytical research as a structurally defined, fluorinated amino acid standard for method development and reference material preparation. The combination of a protected amino group (Cbz carbamate) and a trifluorinated aromatic side chain provides strong mass spectrometric detectability and chromatographic behavior distinct from non-fluorinated analogs. The preserved stereochemistry and defined substitution pattern support use in stereochemical and identity confirmation workflows for fluorinated amino acid derivatives and peptide building blocks. The compound can therefore serve as an analytical anchor for verifying incorporation of fluorinated residues during peptide synthesis, purification monitoring, and downstream characterization of fluorinated products.
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