3-Trifluoromethyl-D-Phenylalanine is a non-proteinogenic, fluorinated amino acid derivative in which the phenylalanine side chain bears a trifluoromethyl substituent at the 3-position of the aromatic ring, and the molecule is specified as the D stereoisomer. It contains both amino and carboxyl functional groups suitable for forming peptide bonds, with the aromatic side chain featuring the electron-withdrawing CF3 group that can modulate hydrophobicity and aromatic interactions while the D configuration influences stereochemical outcomes in peptide and stereoselective assays. This compound is used in peptide chemistry and chemical biology workflows to introduce a fluorinated aromatic residue for structure-activity studies, conformational probing, and analytical method development involving fluorinated amino acid analogues.
CAT No: CP16702
CAS No:14464-67-6
Synonyms/Alias:14464-67-6;(R)-2-AMINO-3-(3-(TRIFLUOROMETHYL)PHENYL)PROPANOICACID;3-(Trifluoromethyl)-D-phenylalanine;D-3-Trifluoromethylphenylalanine;3-Trifluoromethyl-D-Phenylalanine;(2R)-2-amino-3-[3-(trifluoromethyl)phenyl]propanoicacid;D-3-TRIFLUOROMETHYLPHE;SBB063879;(R)-2-Amino-3-[3-(trifluoromethyl)phenyl]propionicacid;TRIFLUOROMETHYPHE;D-3-Trifluoromethyphenylalanine;AC1OCXT0;76029_ALDRICH;D-PHE(3-CF3)-OH;SCHEMBL503602;H-D-PHE(3-CF3)-OH;76029_FLUKA;CTK3J1763;MolPort-001-777-230;ZINC2170206;MFCD01860875;AKOS017482217;AB10089;AC-5863;AM83490
3-Trifluoromethyl-D-Phenylalanine is a D-configured phenylalanine analog bearing a 3-trifluoromethyl substituent on the aromatic ring, introducing strong electron-withdrawing character and increased hydrophobicity. This non-proteinogenic amino acid building block is widely used in medicinal chemistry and peptide/peptidomimetic design to probe how aryl electronics and fluorinated substituents influence structure-activity relationships, conformational preferences, and metabolic stability trends. Its stereochemical specification supports consistent incorporation into synthetic sequences and comparative SAR workflows.
1. Peptidomimetic Building Blocks
3-Trifluoromethyl-D-Phenylalanine is used as a stereodefined amino acid building block for constructing D-amino acid-containing peptides and peptidomimetics in chemical biology and medicinal chemistry programs. Researchers incorporate this aryl-trifluoromethyl residue into short bioactive peptide analogs, cyclic scaffolds, and backbone-modified constructs to systematically evaluate how the fluorinated aromatic side chain affects potency-driving properties and overall molecular behavior. The D-configuration enables access to non-natural peptide architectures that are commonly explored in protease-resistance and stability-focused lead optimization studies, while the 3-CF3 group provides a strong handle for SAR comparison across analog series.
2. Medicinal Chemistry SAR Studies
3-Trifluoromethyl-D-Phenylalanine serves as a precise SAR tool for medicinal chemistry teams developing small-molecule surrogates and peptide-like inhibitors where aryl electronics are tuned for performance. The 3-trifluoromethyl substituent is frequently selected to modulate lipophilicity, aromatic ring polarization, and physicochemical balance relative to unsubstituted or differently substituted phenylalanine analogs. By using a defined D-amino acid stereochemistry, teams can compare stereochemical effects alongside electronic effects, supporting rational optimization of lead series that rely on fluorinated aromatic motifs.
3. Chiral Intermediate For Synthesis
3-Trifluoromethyl-D-Phenylalanine is also used in the preparation of chiral amino acid derivatives and downstream pharmaceutical intermediates where a D-phenylalanine framework with a 3-CF3 aromatic ring is required. Process development and custom synthesis laboratories often select this building block when a stereochemically consistent chiral element must be carried through to later stages, such as formation of protected amino acid intermediates, coupling-ready derivatives, or incorporation into larger synthetic fragments. The fluorinated aromatic side chain provides a chemically robust motif that is valuable for assembling fluorinated libraries and for route development where maintaining the CF3 substitution pattern is critical.
4. Analytical Reference In Fluorinated Studies
3-Trifluoromethyl-D-Phenylalanine is employed as an analytical reference material in method development and characterization workflows involving fluorinated amino acid analogs. Analytical chemists use it to support LC-MS and related quantitation/identification strategies for peptide fragments, amino acid derivatives, and synthetic intermediates that contain the 3-trifluoromethyl aromatic motif. Its defined D-stereochemistry helps distinguish stereoisomeric or isomeric analogs in analytical comparisons, making it useful for confirming identity and monitoring incorporation during synthetic sequence development.
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