Boc-2,4,5-Trifluoro-D-Phenylalanine is a Boc-protected, non-natural fluorinated phenylalanine derivative in which the phenyl side chain bears three fluorine atoms at the 2, 4, and 5 positions and the α-amino acid backbone is in the D stereochemical form. The molecule contains a Boc-protected amino group and a free carboxylic acid, with the electron-withdrawing fluorinated aromatic ring providing altered hydrophobicity and conformational and electronic effects relative to unmodified phenylalanine. It is used as a protected amino acid building block for peptide synthesis and for structure-activity or chemical biology studies where fluorinated aromatic residues are incorporated to tune physicochemical properties and enable analytical differentiation of peptide or amino acid derivatives.
CAT No: CP16905
Boc-2,4,5-Trifluoro-D-Phenylalanine is a Boc-protected, D-configured phenylalanine derivative bearing three fluorine atoms on the aromatic ring, providing a strongly electron-withdrawing, metabolically and chemically distinctive side-chain environment. This fluorinated, stereochemically specified amino acid building block is commonly used in peptide and peptidomimetic synthesis where controlled incorporation of a non-natural aromatic residue is required for structure-activity relationship studies, conformational effects, and analytical traceability. The Boc group supports its use as a protected amino acid intermediate in protected-residue workflows.
1. Peptide Library Building
Boc-2,4,5-Trifluoro-D-Phenylalanine is used by peptide chemistry groups to construct peptide libraries and defined analog series that probe how aromatic fluorination and D-stereochemistry influence structure, stability, and downstream behavior. Because the side chain is pre-functionalized as a protected amino acid building block, it fits directly into standard protected-residue assembly workflows for generating short peptides and constrained peptidomimetics. Researchers frequently select the 2,4,5-trifluoro substitution pattern to introduce a clear chemical handle for comparative characterization by LC-MS and NMR, supporting systematic SAR campaigns where subtle aromatic electronic changes are the variable of interest.
2. Medicinal Chemistry SAR Probes
Boc-2,4,5-Trifluoro-D-Phenylalanine supports medicinal chemistry programs that require fluorinated amino acid residues as SAR probes within peptide-like scaffolds. The tri-fluoro aromatic ring provides a distinct physicochemical signature that can be leveraged during lead optimization to differentiate analogs and rationalize structure-property relationships in series synthesis. Teams developing peptidomimetics and constrained peptide fragments use this building block to introduce stereochemical control at the chiral center while maintaining a protected backbone for reliable incorporation into larger intermediate sequences prior to final coupling and purification.
3. Pharmaceutical Intermediate Synthesis
Boc-2,4,5-Trifluoro-D-Phenylalanine is also used in pharmaceutical intermediate development to prepare fluorinated amino acid fragments and advanced building blocks for downstream manufacturing of peptide-based candidates and related chemical entities. The combination of Boc protection and the non-natural, heavily fluorinated aromatic side chain makes it a practical intermediate for assembling defined residues in multi-step synthesis where protecting-group compatibility and stereochemical fidelity are important. Process and development chemists commonly rely on such protected fluorinated amino acid intermediates to reduce variability across batches when producing structured intermediates for scale-up and analytical method transfer.
4. Analytical Method Development
Boc-2,4,5-Trifluoro-D-Phenylalanine is frequently employed as a reference building block during analytical method development for fluorinated peptide intermediates and analogs, particularly when establishing LC-MS workflows that distinguish closely related aromatic variants. The presence of three fluorine atoms on the phenyl ring provides strong, characteristic mass and fragmentation behavior that can improve method robustness when monitoring synthesis progress, verifying incorporation, and supporting impurity profiling. Analytical laboratories use this compound to generate authentic standards and calibration materials for peptide-like fragments that contain D-configured, fluorinated aromatic residues, enabling consistent identification of target-containing intermediates during development.
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