Cbz-2,4,5-Trifluoro-L-Phenylalanine is a Cbz-protected, fluorinated phenylalanine derivative in which the phenyl side chain bears three fluorine substituents at the 2, 4, and 5 positions, retaining an L stereochemical designation at the α-carbon. The molecule contains an α-amino group masked as a benzyloxycarbonyl (Cbz) carbamate and a free carboxylic acid, while the trifluorinated aromatic ring provides increased electron-withdrawing character and altered hydrophobic/steric properties relative to unmodified phenylalanine. In peptide chemistry, the Cbz-protected amino functionality and carboxylic acid enable stepwise coupling and incorporation of this modified amino acid into protected peptide intermediates for structure-activity studies, chemical biology labeling, and conformational or binding investigations where aryl fluorination effects are examined.
CAT No: CP16908
Cbz-2,4,5-Trifluoro-L-Phenylalanine is an N-Cbz protected L-phenylalanine derivative bearing three fluorine atoms on the aromatic ring at the 2-, 4-, and 5-positions, creating a strongly electron-withdrawing, metabolically stable aryl side chain. The molecule contains a stereogenic α-carbon consistent with the L-configuration of the amino acid backbone, along with a benzyloxycarbonyl (Cbz) carbamate that governs chemoselective N-deprotection during peptide assembly. The trifluorinated phenyl group modulates lipophilicity, polarizability, and conformational preferences, while the protected amine and carboxyl functionality (as present in the provided derivative) support controlled coupling chemistry. The fluorinated aromatic motif can participate in downstream transformations such as selective functionalization of the side-chain aryl ring and serves as a chiral intermediate for preparing fluorinated amino acid building blocks and peptide analogs.
1. Peptide Synthesis
Cbz-2,4,5-Trifluoro-L-Phenylalanine is used in peptide building block preparation where N-Cbz protection enables standard peptide coupling followed by orthogonal deprotection. The L-configuration at the α-carbon provides stereochemical fidelity for incorporation into peptide sequences, while the trifluorinated phenyl side chain functions as a defined aromatic pharmacophore in peptidomimetics and fluorinated analogs. The Cbz carbamate can be removed under hydrogenolysis-compatible conditions to reveal the free amine for subsequent chain elongation or for generating peptide termini. Downstream, fluorinated peptides derived from this amino acid can be used for structure-activity relationship studies and for generating libraries of aryl-substituted peptide analogs with controlled electronic properties.
2. Drug Discovery SAR Studies
Cbz-2,4,5-Trifluoro-L-Phenylalanine is applied in medicinal chemistry research to introduce a trifluorinated aromatic side chain into peptide-like scaffolds for SAR investigations. The electron-withdrawing fluorine pattern at the 2-, 4-, and 5-positions can tune binding-site interactions, aromatic stacking, and local dipole effects, making the residue a useful chiral element for fragment-based molecular design. The protected amino acid form supports conversion into amide-linked derivatives through peptide coupling chemistries, enabling systematic comparison of analogs that vary only in the fluorinated aryl motif. The resulting fluorinated intermediates and peptide analogs can feed iterative design cycles aimed at mapping structure-function relationships in bioactive lead series.
3. Side-Chain Functionalization
Cbz-2,4,5-Trifluoro-L-Phenylalanine is suitable for synthetic organic chemistry workflows that require a protected amino acid precursor bearing a fluorinated aryl handle. The trifluorinated phenyl ring provides a chemically defined platform for further derivatization, including transformations that can introduce additional substituents or enable cross-coupling strategies where compatible functional groups are present in the molecule or introduced later. The Cbz-protected nitrogen and the amino acid backbone enable stepwise functional group interconversions while maintaining stereochemical integrity at the α-carbon. The compound can therefore serve as a chiral intermediate for producing fluorinated aryl-containing amino acid derivatives, peptide fragments, and downstream building blocks used in fine chemical synthesis.
4. Protected Amino Acid Chemistry
Cbz-2,4,5-Trifluoro-L-Phenylalanine is employed as an N-protected amino acid derivative for controlled synthesis of fluorinated peptide building blocks and protected intermediate preparation. The Cbz carbamate offers a predictable protection strategy for managing chemoselectivity during coupling, purification, and sequential functional group manipulations in multi-step syntheses. The L-stereocenter supports stereospecific incorporation into amide frameworks, while the trifluorinated aromatic side chain remains intact under typical peptide construction conditions, providing a stable stereochemical and electronic element. The compound can be applied to generate orthogonally protected sequences or to produce deprotected fluorinated amino acid forms for subsequent derivatization in biochemical research intermediate pipelines.
5. Pharmaceutical Manufacturing Intermediates
Cbz-2,4,5-Trifluoro-L-Phenylalanine is relevant to pharmaceutical manufacturing and process chemistry as a fluorinated chiral intermediate for producing peptide-based active ingredients and related intermediates. The protected amine and the amino acid backbone structure support scalable peptide coupling and controlled deprotection logic, which is central to manufacturing route design for fluorinated residues. The trifluorinated aromatic side chain can contribute to improved chemical stability of peptide analogs during downstream processing and formulation development, while the defined stereochemistry reduces variability in intermediate quality. The compound can be incorporated into industrial workflows that require consistent fluorinated amino acid incorporation into well-defined amide-linked products and manufacturing-ready peptide fragments.
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