Boc-4-Trifluoromethyl-D-Phenylalanine is a protected, non-natural amino acid derivative in which the amino group is masked as a Boc (tert-butoxycarbonyl) carbamate and the side chain is a 4-trifluoromethyl-substituted benzyl group attached to the alpha carbon of the D-phenylalanine scaffold. The molecule contains both a Boc-protected amino functionality and a free carboxylic acid group, with the trifluoromethyl substituent imparting strong electron-withdrawing character and increased hydrophobicity at the aromatic ring while the D stereochemical configuration is specified by the name. In peptide chemistry and chemical biology workflows, this Boc-protected amino acid is used as a building block for stepwise peptide assembly and for preparing structurally defined analogues in structure-activity and labeling studies where an aryl CF3 functionality is incorporated.
CAT No: CP16805
CAS No:82317-83-7
Synonyms/Alias:82317-83-7;Boc-4-(trifluoromethyl)-D-phenylalanine;Boc-D-Phe(4-CF3)-OH;BOC-D-4-TRIFLUOROMETHYLPHE;(R)-2-((tert-Butoxycarbonyl)amino)-3-(4-(trifluoromethyl)phenyl)propanoicacid;Boc-D-4-Trifluoromethylphenylalanine;Boc-4-Trifluoromethyl-D-Phenylalanine;SBB064602;(2R)-2-[(tert-butoxycarbonyl)amino]-3-[4-(trifluoromethyl)phenyl]propanoicacid;(R)-2-(TERT-BUTOXYCARBONYLAMINO)-3-(4-(TRIFLUOROMETHYL)PHENYL)PROPANOICACID;Boc-L-phe(4-CF3)-OH;AC1MC51U;15016_ALDRICH;SCHEMBL3556235;15016_FLUKA;CTK8C5719;MolPort-001-773-106;SMVCCWNHCHCWAZ-LLVKDONJSA-N;ZINC2569504;KM2113;MFCD00797557;AKOS015890209;AB07177;AM83502;BOC-D-4-TRIFLUOROMETHYL-PHE-OH
Boc-4-Trifluoromethyl-D-Phenylalanine is a D-configured phenylalanine derivative bearing a Boc-protecting group on the amino functionality and a 4-trifluoromethyl substituent on the aromatic ring. This combination of stereochemical control and electron-withdrawing aryl functionality makes it a practical building block for assembling non-natural or conformationally tuned peptide segments and for preparing medicinal chemistry intermediates where fluorinated aromatic motifs are required. Researchers typically select this protected amino acid when they need a defined stereochemical residue and a stable, isolable form compatible with peptide coupling workflows.
1. Peptide Segment Building
Boc-4-Trifluoromethyl-D-Phenylalanine is used as a protected amino acid building block for constructing peptide segments that incorporate a D-amino acid residue and a 4-trifluoromethyl-substituted aromatic side chain. Peptide chemists and custom synthesis groups rely on Boc-protected inputs to deliver consistent coupling performance in solution-phase or protected-amino-acid workflows, enabling the preparation of D-residue-containing peptides used for structure-activity relationship studies, protease stability screening, and conformational comparison panels. The 4-trifluoromethyl group provides a fluorinated aromatic handle that is commonly leveraged to modulate physicochemical properties of peptide-like scaffolds without changing the backbone connectivity.
2. Medicinal Chemistry Intermediate
Boc-4-Trifluoromethyl-D-Phenylalanine serves as a stereodefined intermediate for medicinal chemistry programs that require fluorinated phenylalanine analogs. Medicinal chemistry teams use this type of protected amino acid to access aryl-trifluoromethyl motifs in peptidomimetic series, where the D-configuration and protected amine allow downstream transformations into amides, activated fragments, or residue-level modifications during lead optimization. The presence of the Boc group supports controlled functional-group manipulation, while the electron-withdrawing trifluoromethyl substituent helps rationalize how aromatic electronics and hydrophobic character translate into measurable structure-property trends in small-molecule and peptide-derived libraries.
3. Stereocontrolled SAR Libraries
Boc-4-Trifluoromethyl-D-Phenylalanine is frequently selected for generating stereochemically defined SAR libraries that compare L- versus D-residue effects and evaluate the impact of fluorinated aromatic substitution patterns. Chemical biology and peptide drug discovery groups incorporate this residue into short, residue-defined constructs to probe how side-chain electronics and stereochemistry influence folding propensity, binding-site complementarity, and overall scaffold behavior in biochemical assays. Because the input is already protected at the amino terminus and carries a specific D stereocenter, it supports reproducible library synthesis where each variant differs by residue identity rather than by protecting-group or stereochemical variability.
1. Implications of ligand-receptor binding kinetics on GLP-1R signalling
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