Fmoc-2,4,5-Trifluoro-L-Phenylalanine is a protected, fluorinated phenylalanine derivative in which the amino acid side chain is a trisubstituted phenyl ring bearing fluorine atoms at the 2, 4, and 5 positions, and the α-amino group is capped with an Fmoc carbamate. The molecule retains a free carboxyl group for coupling chemistry and presents the stereogenic center in the L configuration as indicated by the product name, while the electron-withdrawing fluorines modulate the aromatic ring's polarity and hydrogen-bonding characteristics. As an Fmoc-protected amino acid, it is used in stepwise peptide synthesis and structure-activity or binding studies where incorporation of a fluorinated aromatic residue provides a defined handle for tuning physicochemical properties and supporting analytical characterization of peptide or protein analogs.
CAT No: CP16906
Fmoc-2,4,5-Trifluoro-L-Phenylalanine is an Fmoc-protected L-phenylalanine derivative bearing three fluorine substituents at the 2-, 4-, and 5-positions of the aromatic ring. The molecule contains a chiral α-carbon consistent with L-stereochemistry, an Fmoc carbamate on the α-amino group for base-labile protection during peptide assembly, and a carboxylic acid functionality that can be activated for coupling or further protected depending on the synthetic plan. The electron-withdrawing trifluorinated aryl side chain modulates hydrophobicity, metabolic stability, and conformational preferences relative to non-fluorinated phenylalanine analogs, while the aromatic fluorines provide handles for NMR and mass spectrometric discrimination as well as for downstream derivatization or cross-coupling strategies. The combined presence of an Fmoc-protected amine and a reactive carboxyl group makes the compound suitable as a chiral amino acid intermediate and peptide building block for constructing fluorinated peptidic and peptidomimetic structures.
1. Peptide Synthesis
Fmoc-2,4,5-Trifluoro-L-Phenylalanine supports solid-phase peptide synthesis and related coupling workflows because the Fmoc group protects the α-amine during chain elongation and can be removed under standard base conditions to reveal the reactive amino functionality for subsequent peptide bond formation. The L-configuration at the stereogenic center provides stereochemical fidelity in the growing peptide, while the trifluorinated phenyl side chain functions as a defined hydrophobic/aromatic motif that can influence local packing and backbone torsion. The carboxylic acid can be activated for amide coupling to incorporate the fluorinated residue at internal positions or at termini when paired with appropriate terminal protection strategies. Fluorinated peptide products generated from this building block can serve as research-grade materials for studying fluorine effects on peptide conformation and for preparing defined analog libraries for structure-activity relationship studies.
2. Peptidomimetics And SAR
Fmoc-2,4,5-Trifluoro-L-Phenylalanine is suitable for medicinal chemistry-oriented peptidomimetic construction where aromatic fluorination is used to tune physicochemical properties and molecular recognition. The trifluorinated phenyl ring can alter electron density and aromatic interactions, while the stereodefined α-amino acid backbone enables incorporation into constrained scaffolds that preserve the spatial arrangement of side-chain substituents. Fmoc protection supports iterative synthesis of analog series that vary only by side-chain electronics, allowing structure-activity relationship studies to correlate fluorination patterns with binding or stability proxies in biochemical assays. Downstream, the fluorinated residue can be carried into larger fragments for fragment-based molecular design and SAR refinement, and the aryl fluorines can facilitate analytical tracking by 19F NMR and characteristic mass transitions.
3. Side-Chain Functionalization
Fmoc-2,4,5-Trifluoro-L-Phenylalanine can serve as a chiral aromatic intermediate for side-chain functionalization strategies that exploit the fluorinated substitution pattern on the phenyl ring. The presence of three aryl fluorines provides a spectroscopically distinct signature for monitoring transformations and can participate in synthetic planning for selective substitution, cross-coupling, or derivatization routes that convert the trifluorinated arene into new functional motifs while retaining the L-amino acid stereocenter. The Fmoc-protected amine and carboxylic acid enable orthogonal protection and selective deprotection sequences, allowing the aryl modification to be integrated either before or after peptide assembly depending on the chosen protecting-group scheme. Resulting fluorinated amino acid derivatives and modified peptidic intermediates can feed into fine chemical synthesis programs and support the preparation of labeled or functionalized scaffolds for chemical biology research.
4. Chemical Biology Probes
Fmoc-2,4,5-Trifluoro-L-Phenylalanine is applicable to chemical biology workflows that require incorporation of fluorinated amino acid residues into peptides used as probes for molecular recognition and interaction mapping. The Fmoc-protected amino group enables controlled installation into defined sequences, while the trifluorinated aromatic side chain provides a strong 19F NMR handle that can be leveraged for conformational readouts, binding-state monitoring, or environment-sensitive spectral changes. The stereodefined backbone supports reproducible peptide folding tendencies, which can be critical when comparing probe behavior across analog series. Fluorinated peptide probes prepared from this building block can also be used as biochemical research intermediates for generating sequence-defined materials for downstream conjugation and analytical characterization.
5. Pharmaceutical Intermediate Preparation
Fmoc-2,4,5-Trifluoro-L-Phenylalanine functions as a process-relevant, chiral amino acid intermediate for manufacturing routes that require incorporation of fluorinated aromatic residues into drug-like peptides, peptidomimetics, or protease-modulating scaffolds. The Fmoc carbamate provides a robust protection strategy for amine handling during multi-step synthesis, and the L-stereochemistry supports predictable stereochemical outcomes in downstream coupling and deprotection operations. The carboxylic acid can be converted into activated derivatives or further protected as needed to align with industrially scalable peptide coupling chemistries and purification constraints. Resulting fluorinated intermediates can be carried forward into specialty chemical production for defined fluorinated building blocks, enabling consistent preparation of larger molecular entities used in applied medicinal chemistry programs.
6. Analytical Standards And Labeling
Fmoc-2,4,5-Trifluoro-L-Phenylalanine is suitable for analytical research and method development where fluorinated amino acid standards are required for quantification, identification, and structural confirmation. The three aryl fluorines provide a distinctive 19F NMR and mass spectrometric signature, supporting unambiguous detection of the residue in complex peptide mixtures and degradation products. The Fmoc-protected form helps maintain chemical stability during sample handling and supports consistent incorporation into reference peptides used for calibration or LC-MS method validation. The compound can therefore serve as a biochemical research intermediate for preparing reference materials, isotope-compatibility studies, and peptide-based analytical controls that improve confidence in characterization of fluorinated peptide libraries.
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