Boc-3-Trifluoromethyl-D-Phenylalanine is a Boc-protected, non-natural amino acid derivative in which the phenylalanine scaffold bears a 3-trifluoromethyl substituent on the aromatic ring and the stereochemical form is specified as D. The molecule contains a Boc-protected amino functionality and a free carboxylic acid group, while the side chain features a substituted benzyl moiety with a strongly electron-withdrawing trifluoromethyl group that can influence hydrophobicity and conformational preferences in peptide contexts. As a protected amino acid building block, it is used in peptide synthesis and structure-activity or chemical biology studies to introduce the trifluoromethyl-bearing D-phenylalanine residue with controlled chemoselectivity during stepwise coupling and subsequent deprotection.
CAT No: CP16705
CAS No:82317-82-6
Synonyms/Alias:82317-82-6;Boc-3-(trifluoromethyl)-D-phenylalanine;Boc-D-Phe(3-CF3)-OH;(R)-2-((tert-Butoxycarbonyl)amino)-3-(3-(trifluoromethyl)phenyl)propanoicacid;BOC-D-3-TRIFLUOROMETHYLPHE;Boc-D-3-Trifluoromethylphenylalanine;Boc-3-Trifluoromethyl-D-Phenylalanine;(2R)-2-[(tert-butoxycarbonyl)amino]-3-[3-(trifluoromethyl)phenyl]propanoicacid;Boc-L-phe(3-CF3)-OH;(2R)-2-(tert-butoxycarbonylamino)-3-[3-(trifluoromethyl)phenyl]propanoicacid;AC1MC51R;15012_ALDRICH;SCHEMBL3556619;15012_FLUKA;CTK8C5726;MolPort-001-771-178;ZINC2567678;KM2112;PC0938;AKOS025117413;AB06802;AM83493;BOC-D-3-TRIFLUOROMETHYL-PHE-OH;CB-1283;BOC-D-PHE(3-TRIFLUOROMETHYL)-OH
Boc-3-Trifluoromethyl-D-Phenylalanine is a D-configured, non-proteinogenic amino acid building block bearing a Boc-protected alpha-amino group and a 3-trifluoromethyl-substituted phenyl side chain. Its strongly electron-withdrawing CF3 group and stereochemical definition make it a useful chiral intermediate for constructing fluorinated peptidomimetics and peptide analogs where side-chain electronics and sterics are tuned for structure-activity relationship studies. The protected format supports downstream peptide-coupling workflows used in medicinal chemistry and custom peptide manufacturing.
1. Peptidomimetic Building Blocks
Boc-3-Trifluoromethyl-D-Phenylalanine is used by medicinal chemistry groups to assemble D-amino-acid-containing peptidomimetics and constrained peptide analogs for SAR campaigns. The Boc protection enables reliable incorporation into protected peptide fragments during custom synthesis, while the 3-trifluoromethyl phenyl side chain provides a distinctive fluorinated motif that is often leveraged to modulate physicochemical properties and conformational preferences in lead optimization. Researchers frequently select this specific D stereochemistry when designing analog series that probe stereochemical effects on structure and function.
2. Solid-Phase Peptide Fragment Assembly
Boc-3-Trifluoromethyl-D-Phenylalanine serves as a defined amino acid component for peptide fragment construction workflows where D-residues are introduced intentionally to alter peptide backbone stereochemistry. In solid-phase or fragment-based assembly strategies, the Boc-protected amine form supports controlled coupling into larger sequences, enabling consistent placement of the fluorinated aromatic side chain within a peptide scaffold. This is particularly relevant for teams producing modified peptide libraries for chemical biology screening, where reproducible building blocks and stereochemical fidelity are essential for downstream analytical comparison.
3. Pharmaceutical Intermediate Development
Boc-3-Trifluoromethyl-D-Phenylalanine is also used as a chiral, protected intermediate in the development of fluorinated amino acid derivatives and related medicinal chemistry intermediates. Process chemistry and discovery chemistry teams rely on this kind of protected building block to access D-configured fluorinated motifs that can be further transformed into specialized analogs, including protected or activated derivatives used in subsequent coupling steps. The presence of the Boc group and the CF3-substituted aromatic side chain makes it a practical starting material for building diversified fluorinated series used in lead optimization and analog synthesis planning.
4. Chiral SAR Analog Synthesis
Boc-3-Trifluoromethyl-D-Phenylalanine supports chiral structure-activity relationship studies where researchers compare stereochemical variants and side-chain electronic effects across closely related analogs. The D configuration allows direct evaluation of stereochemical contributions, while the 3-trifluoromethyl substituent provides a strong handle for tuning hydrophobicity and electronic character within an otherwise comparable aromatic framework. This building block is commonly selected when investigators need a single, well-defined fluorinated residue to generate a consistent set of analogs for comparative characterization by LC-MS, NMR, and chromatographic profiling.
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