Fmoc-2,4,6-Trifluoro-D-Phenylalanine is an Fmoc-protected, non-natural amino acid derivative featuring a D-phenylalanine backbone bearing three fluorine atoms at the 2, 4, and 6 positions of the aromatic ring. The molecule contains an Fmoc-protected amino group and a free carboxyl group, with the fluorinated phenyl side chain providing increased electronegativity and altered hydrophobic/aromatic character relative to unsubstituted phenylalanine. In peptide synthesis and structure-activity studies, it functions as a protected building block for incorporating a fluorinated, stereodefined phenylalanine analogue into peptides to support chemical probing, molecular labeling, and conformational or binding investigations.
CAT No: CP17007
Fmoc-2,4,6-Trifluoro-D-Phenylalanine is an Fmoc-protected, D-configured phenylalanine derivative in which the aromatic ring is substituted with three fluorine atoms at the 2,4,6-positions. The molecule combines a stereogenic alpha-carbon typical of amino acid chemistry with an Fmoc carbamate that supports standard solid-phase peptide synthesis handling and orthogonal deprotection workflows. The electron-withdrawing trifluoromethyl-free aryl fluorination pattern modulates side-chain polarity and reactivity, enabling controlled incorporation of a fluorinated aromatic motif into peptide sequences and peptidomimetics. The presence of the protected amine and the carboxyl functionality suitable for coupling chemistry makes the compound a chiral, fluorinated amino acid building block and a downstream intermediate for synthetic and biochemical research.
1. Peptide Synthesis
Fmoc-2,4,6-Trifluoro-D-Phenylalanine is applied in peptide building block workflows for solid-phase and solution-phase assembly where Fmoc removal and subsequent amide bond formation depend on the protected amino group. The D-configuration at the alpha-carbon provides stereochemical control for backbone conformation and for studies of D-amino acid incorporation effects on peptide stability and folding. The 2,4,6-trifluorinated phenyl side chain functions as a chemically robust aromatic group that can be introduced without requiring additional side-chain protection during coupling. The resulting fluorinated peptide analogs can be used to generate structure-defined libraries for peptide science and to prepare intermediates for further derivatization at the peptide level.
2. Peptidomimetics And SAR
Fmoc-2,4,6-Trifluoro-D-Phenylalanine is utilized in peptidomimetic design and structure-activity relationship studies where a fluorinated aromatic residue serves as a tunable physicochemical handle. The aryl fluorination at 2,4,6-positions alters hydrogen-bonding patterns, aromatic electronics, and steric presentation relative to unsubstituted phenylalanine, while the D-amino acid stereochemistry supports exploration of conformational constraints. The Fmoc-protected amine enables stepwise incorporation into larger scaffolds, supporting systematic variation of residue position and sequence context. Downstream, fluorinated analogs prepared from this chiral building block can be used to support SAR mapping, generate reference compounds for binding studies, and supply standards for method development in medicinal chemistry research.
3. Chiral Building Blocks
Fmoc-2,4,6-Trifluoro-D-Phenylalanine is employed as a chiral amino acid intermediate for stereoselective synthesis programs that require D-configured backbone elements. The defined stereocenter and the Fmoc carbamate provide a protected, configurationally stable platform for sequential functionalization during peptide coupling or for conversion into other protected forms. The trifluorinated aromatic side chain offers a distinct mass and electronic signature that can be leveraged for traceable intermediate tracking and for constructing fluorinated fragments in synthetic organic chemistry. The compound can be applied to produce chiral fluorinated derivatives used as reference materials, scaffold components, or synthetic intermediates feeding into larger fine chemical manufacturing routes.
4. Chemical Biology Probes
Fmoc-2,4,6-Trifluoro-D-Phenylalanine is applied in chemical biology research where fluorinated aromatic residues can be incorporated into peptides or protein-interacting motifs for labeling and interaction studies. The Fmoc-protected amino functionality supports controlled assembly of D-amino acid-containing probes, while the trifluorinated phenyl side chain can serve as a spectroscopically and analytically distinctive element for monitoring incorporation. The D-configuration can be used to probe protease resistance or to modulate binding conformations in assays that compare L- versus D-containing analogs. Downstream, fluorinated peptide probes derived from this building block can be adapted into conjugatable constructs for biomolecular interaction mapping and method development.
5. Pharmaceutical Intermediate Preparation
Fmoc-2,4,6-Trifluoro-D-Phenylalanine is suitable for pharmaceutical intermediate preparation in synthetic routes that require Fmoc-protected, stereodefined amino acid residues for manufacturing of peptide-like candidates or process intermediates. The Fmoc group enables standardized protection management during stepwise assembly, supporting reproducible coupling chemistry and subsequent deprotection strategies aligned with peptide manufacturing workflows. The 2,4,6-trifluorinated aromatic side chain contributes a stable, electron-poor aryl motif that can be carried through intermediate stages without introducing labile side-chain protecting groups. The resulting fluorinated peptide fragments and intermediates can be used for downstream scale-up synthesis, analytical reference preparation, and controlled generation of final fluorinated products.
6. Analytical Research Standards
Fmoc-2,4,6-Trifluoro-D-Phenylalanine is utilized for analytical research and method validation where a defined D-configured, Fmoc-protected amino acid with a trifluorinated aromatic signature supports unambiguous detection. The combination of Fmoc chromophore and the 2,4,6-trifluorinated phenyl group can facilitate LC-MS and NMR-based tracking of incorporation, deprotection, and purification stages in peptide chemistry workflows. The stereochemical definition at the alpha-carbon allows use as a reference standard when distinguishing D- versus L-containing residues in synthetic libraries or process monitoring. Downstream, fluorinated standards derived from this compound can be employed to calibrate analytical methods, support impurity profiling, and provide structurally consistent controls for amino acid derivative characterization.
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