Fmoc-2,4,5-Trifluoro-D-Phenylalanine is a protected, fluorinated aromatic amino acid derivative in which the phenylalanine side chain bears three fluorine substituents at the 2, 4, and 5 positions and the amino acid is provided in the D stereochemical form. The molecule contains an Fmoc-protected amino group and a free carboxylic acid, with the electron-withdrawing trifluoromethyl-free aryl fluorination altering side-chain polarity and aromatic character while maintaining the α-amino acid backbone for peptide coupling. In synthesis, it is used as a building block for stepwise peptide assembly where the Fmoc group supports controlled protection of the α-amino functionality and the fluorinated phenyl side chain provides a handle for structure-activity studies, conformational probing, and analytical differentiation of fluorinated peptide analogues.
CAT No: CP16907
Fmoc-2,4,5-Trifluoro-D-Phenylalanine is an Fmoc-protected, D-configured phenylalanine derivative in which three fluorine atoms are installed at the 2, 4, and 5 positions of the aromatic ring. The molecule contains a stable fluorenylmethoxycarbonyl (Fmoc) group on the α-amino functionality, a free carboxylate equivalent within the protected amino acid framework, and a chiral stereocenter at the amino acid α-carbon that is fixed to the D-configuration. The perfluorinated aromatic ring modulates electronic density and increases hydrophobicity and metabolic stability relative to non-fluorinated analogs, while maintaining an aromatic handle for π-interactions and conformational effects in peptide contexts. The combination of Fmoc protection and a stereodefined amino acid core makes the compound suitable for peptide building block preparation and downstream derivatization where controlled deprotection and coupling chemistries are required.
1. Peptide Synthesis
Fmoc-2,4,5-Trifluoro-D-Phenylalanine supports solid-phase peptide synthesis and fragment assembly workflows for generating D-phenylalanine-containing sequences. The Fmoc group enables standard N-terminal protection and orthogonal deprotection strategies, while the chiral α-carbon stereochemistry provides stereochemical control during peptide coupling. The trifluorinated phenyl side chain can influence local folding, aromatic packing, and resistance to oxidative side reactions, which is relevant for preparing fluorinated peptide analogs for structure-activity relationship studies. The resulting peptide products can be carried forward to purification, analytical characterization, and comparative scaffold generation in amino acid chemistry and peptide science.
2. Peptidomimetics And SAR
Fmoc-2,4,5-Trifluoro-D-Phenylalanine is used in peptidomimetic design and SAR-focused molecular scaffold construction where fluorinated aromatic residues tune physicochemical properties. The 2,4,5-trifluoro substitution pattern changes ring electronics and can alter hydrogen-bonding patterns at nearby heteroatoms in the peptide backbone environment, while the D-configuration can affect overall conformational preferences. Fmoc-protected incorporation into peptide analogs enables systematic side-chain functional variation while keeping the backbone coupling chemistry consistent across analog series. Downstream, the fluorinated D-phenylalanine residue can be used to generate libraries of analogs for mapping structure-property relationships and refining molecular recognition motifs.
3. Chemical Biology Labeling
Fmoc-2,4,5-Trifluoro-D-Phenylalanine can serve as a chemically defined amino acid building block for chemical biology workflows that require incorporation of fluorinated aromatic motifs into peptides or protein fragments. The Fmoc-protected amino acid format supports controlled placement into bioactive peptide probes, and the D-stereochemistry provides a handle for studying stereochemical effects on binding or protease stability in biochemical assays. The trifluorinated aromatic ring can function as a spectroscopically informative tag for NMR-based tracking and can also modulate hydrophobic interactions that govern probe localization and retention. The resulting labeled constructs can be employed as research intermediates for biomolecule modification and molecular recognition studies where fluorinated side chains improve assay robustness.
4. Protected Amino Acid Chemistry
Fmoc-2,4,5-Trifluoro-D-Phenylalanine is suitable for protected amino acid synthesis planning that relies on orthogonal protection and predictable coupling behavior. The Fmoc group provides a removable N-protection strategy compatible with peptide coupling cycles, while the D-phenylalanine core preserves stereochemical integrity through intermediate handling. The electron-poor, highly fluorinated aromatic side chain can tolerate many peptide-manufacturing conditions without undergoing side reactions that are common for more reactive substituents, supporting its role as a stable chiral building block. The compound thereby functions as a chiral synthetic intermediate for producing fluorinated peptide building blocks and for preparing downstream derivatives requiring controlled deprotection and residue-specific incorporation.
5. Pharmaceutical Intermediate Preparation
Fmoc-2,4,5-Trifluoro-D-Phenylalanine can be applied in pharmaceutical intermediate preparation for fluorinated peptide-like structures used in process-oriented fine chemical synthesis. The protected amino acid architecture, including the Fmoc carbamate and stereodefined α-amino acid center, aligns with manufacturing routes that assemble complex intermediates by iterative coupling and purification. The trifluorinated aromatic side chain supports generation of analogs with altered lipophilicity and metabolic stability profiles, which is relevant for producing processable chemical entities and reference standards. Downstream, the compound can be incorporated into larger synthetic sequences that yield peptide intermediates, peptidomimetic fragments, and analytical materials for quality control and method development.
6. Process Chemistry and Fine Chemical Synthesis
Fmoc-2,4,5-Trifluoro-D-Phenylalanine is relevant to process chemistry and specialty chemical production where reproducible chiral amino acid building blocks are required. The combination of a single stereocenter at the α-carbon and a robust Fmoc-protected amine supports scalable peptide building block preparation and controlled deprotection/coupling cycles in automated synthesis environments. The trifluorinated aromatic ring provides a chemically stable motif that can be carried through multi-step syntheses with reduced risk of side-chain oxidation or electrophilic aromatic substitution under typical peptide synthesis conditions. The compound can therefore be employed as a defined intermediate for manufacturing fluorinated peptide analogs, peptidomimetic scaffolds, and other amino acid-derived fine chemicals that depend on stereochemical fidelity and functional-group compatibility.
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