Cbz-2-Trifluoromethyl-L-Phenylalanine is a Cbz-protected, L-configured amino acid derivative in which the phenylalanine side chain bears a 2-trifluoromethyl substituent, making it a fluorinated, non-proteinogenic analogue suitable for peptide chemistry. The molecule contains a free carboxyl group and an N-terminus masked as a benzyloxycarbonyl (Cbz) carbamate, which suppresses amino-group reactivity while retaining the carboxyl functionality for coupling. In synthesis, it is employed as a protected amino acid building block for stepwise assembly of modified peptides and for structure-activity or labeling studies where the trifluoromethyl group provides distinct electronic and hydrophobic characteristics.
CAT No: CP16608
Cbz-2-Trifluoromethyl-L-Phenylalanine is an N-Cbz protected L-phenylalanine derivative bearing a stereogenic α-carbon and a 2-trifluoromethyl-substituted side chain on the aromatic ring. The molecule combines a benzyloxycarbonyl (Cbz) carbamate-protected amino group with a free carboxylic acid, enabling controlled peptide coupling at the C-terminus while maintaining orthogonality to side-chain transformations. The electron-withdrawing trifluoromethyl substituent modulates aromatic reactivity, conformational preferences, and hydrophobicity, which can influence coupling outcomes and downstream derivatization chemistry. As a chiral amino acid intermediate, it is suitable for protected amino acid synthesis workflows and for constructing fluorinated peptide analogs and peptidomimetic scaffolds where stereochemical fidelity at the L-configuration is required.
1. Peptide Synthesis
Cbz-2-Trifluoromethyl-L-Phenylalanine supports peptide building-block preparation in solid-phase or solution-phase peptide synthesis by pairing an N-Cbz carbamate with a carboxylic acid handle for amide bond formation. The Cbz group provides a stable protection strategy during coupling and subsequent side-chain manipulations, while the L-configuration at the α-carbon preserves stereochemical integrity of the incorporated residue. The 2-trifluoromethyl aromatic side chain can be used to tune local hydrophobicity and electronic character in peptide sequences, enabling the construction of fluorinated analog libraries for structure-activity relationship studies. Downstream Cbz removal and sequential coupling steps can generate longer peptide chains containing this fluorinated phenylalanine unit for biochemical research and synthetic methodology development.
2. Peptidomimetics And SAR
Cbz-2-Trifluoromethyl-L-Phenylalanine is applicable to peptidomimetic construction and SAR-focused medicinal chemistry workflows where fluorinated aromatic residues help probe binding-site interactions. The protected amino functionality and free carboxyl group allow conversion into activated coupling partners or incorporation into scaffold fragments while maintaining a defined stereochemical element. The trifluoromethyl substituent can participate in modulating aromatic stacking, dipole effects, and metabolic stability proxies, making the residue suitable for generating analog series that vary only in side-chain electronics and hydrophobic surface. The resulting fluorinated peptide-like structures can serve as chemically defined intermediates for SAR mapping, fragment elaboration, and iterative structure refinement in applied discovery chemistry.
3. Chemical Biology Labeling
Cbz-2-Trifluoromethyl-L-Phenylalanine can be employed in chemical biology research for preparing amino-acid-derived probes and conjugation-ready intermediates. The Cbz-protected amine enables controlled deprotection to reveal a primary amine for subsequent functionalization, while the carboxylic acid supports formation of amide or ester linkages to labeling handles such as linkers, affinity tags, or detection motifs. The fluorinated aromatic side chain provides a chemically stable motif that can be used in tracer design, including incorporation into peptide conjugates where fluorinated residues improve detectability in analytical workflows. The compound's chiral center and protected-group strategy support consistent synthesis of stereochemically defined conjugates for downstream biomolecule modification studies.
4. Process Chemistry Intermediate
Cbz-2-Trifluoromethyl-L-Phenylalanine is suitable for process chemistry intermediate preparation in fine chemical manufacturing due to its clear protection/deprotection logic and defined functional group set. The N-Cbz carbamate and carboxylic acid combination supports scalable peptide-coupling chemistry while allowing orthogonal handling of the amino functionality during intermediate isolation and purification. The trifluoromethyl-substituted aromatic ring can be leveraged as a robust, non-labile structural element in manufacturing routes that require chemical stability across multiple transformations. The compound can therefore serve as a chiral building block for industrial synthesis of fluorinated amino acid derivatives, peptide intermediates, and peptidomimetic fragments used in applied research and specialty chemical production.
5. Analytical Research Standards
Cbz-2-Trifluoromethyl-L-Phenylalanine can function as an analytical reference material for method development and characterization of fluorinated amino acid derivatives. The presence of a stereogenic α-carbon and a defined N-protection state (Cbz) enables unambiguous tracking of protected amino acid intermediates during synthesis, purification, and deprotection monitoring. The trifluoromethyl group provides a distinctive chemical signature that can support chromatographic and spectrometric discrimination from non-fluorinated phenylalanine analogs. The compound can be utilized to prepare standards for confirming incorporation of the fluorinated residue in peptides, verifying stereochemical outcomes, and calibrating analytical assays used in applied peptide chemistry and quality control workflows.
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